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Northern Italia Adventure: September 2026

Northern Italia Adventure: September 2026 image

Northern Italia Adventure

Embark on an unforgettable journey through Northern Italy, where history, culture, and culinary delights come alive in stunning landscapes. Beginning in Lake Como, we’ll explore the charming villages of Varenna and Bellagio, renowned for their colorful streets and alpine views, before gliding across the lake’s glacial waters on a private boat to the historic Villa Balbianello. Our adventure continues with a scenic transfer to Tirano and a breathtaking ride on the Bernina Express through wild gorges and icy glaciers, culminating in the elegance of St. Moritz, Switzerland.

As we venture into Cinque Terre, we’ll uncover the rugged beauty of its five cliffside villages, savoring Ligurian specialties like pesto and sciacchetrà wine. In Bologna, we will discover that this medieval university town is perhaps best described as Italy's stomach! As the birthplace of tortellini and mortadella... we will visit gastronomic treasures such as a Parmigiano Reggiano cheese production, a balsamic vinegar production, and a prosciutto production.

In Tuscany, our luxurious private villa will serve as a serene home base for exploring medieval treasures in Siena, Florence, Montepulciano, Pienza, and other Tuscan hilltop villages.  Along the way, we’ll experience several of Tuscany’s world-class wineries, all while delving into the art, history, and vibrant culture of this iconic region. 

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Overview

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Map

1. Milan

Milan, Metropolitan City of Milan, Italy

2. Bellagio

22021 Bellagio CO, Italy

3. Varenna

23829 Varenna LC, Italy

4. Saint Moritz

7500 St Moritz, Switzerland

5. Monterosso al Mare

19016 Monterosso al Mare, SP, Italy

6. Bologna

Bologna, Metropolitan City of Bologna, Italy

7. Fattoria Torre a Cona

Località Torre a Cona, 50067 Rignano sull'Arno FI, Italy

8. Montepulciano

53045 Montepulciano, Province of Siena, Italy

9. Pienza

53026 Pienza, Province of Siena, Italy

10. Siena

53100 Siena, Province of Siena, Italy

11. Florence

Florence, Metropolitan City of Florence, Italy

12. Pisa

Pisa, Province of Pisa, Italy

13. Lucca

55100 Lucca, Province of Lucca, Italy

Information & Documents

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Welcome to Keyrow Tours

Dear valued guest, 

Thank you very much for choosing Keyrow Tours, a family company specializing in small group travel for over 20 years.

Our aim is to provide a unique and authentic experience of Italy, that exceeds personal hopes and expectations. We believe that we achieve that goal by focusing on immersive cultural experiences, such as local food and wine tastings, hands-on cooking classes, guided tours of historical sites, and interactions with locals. Of course we will visit the main attractions on each of our trips, but we especially love to explore off-the-beaten-path places that truly capture the essence of Italy. 

Thank you again for choosing Keyrow Tours. We are delighted to host this extraordinary trip with you. Our time together will be recreational, educational, and experiential…with memories to last a lifetime. Please contact us with any questions, and know that we remain at your service. "Andiamo!" ("Let's Go!")

With kind regards, 

Paolo C. Carman
Owner and Director

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Your Digital Itinerary

Prior to your trip, each guest will receive an email invitation to download our digital itinerary onto your smartphones or computers. That version of the itinerary will be more detailed than the website version that you are viewing at this time. It will eventually include flight information, departure times, meeting points, helpful tips on what to pack, information about money, hotel contact information, and more. 

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What is the "Day's Recap: a reflection"?

Keyrow Tours coordinates the ambiance and the magic of travel. However, YOU are the travelers soaking in the experience. You become the experts! 

Each evening, a few guests will be asked to present a brief reflection: there is no right or wrong with your reflection.

This could be something simple like sharing what your favorite observation was from earlier in the day. Previous Keyrow travelers have read passages from books, shared prior travel memories, created custom poems, and offered personal thoughts on their life's journey…the possibilities are endless!

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Thoughts for your Consideration! -.pdf

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Italy Packing List*

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Helpful Tips for Sleeping on the Airplane.pdf

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Movie Entertainment Before and After Your Trip

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Italian Words and Phrases.pdf

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What's Included, What's Not

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What's included

Historic Hotels

Centrally located historic hotels (double room occupancy)

Transportation

All ground and sea transportation

Entrance tickets

to museums and special events such as cooking classes and wine tastings

European breakfasts

Daily

Main meals

daily exquisite traditional main meals with local wine

Select light meals

All taxes

Tips

Private walking tours

with your personal Keyrow host

What's not included

Airfare

Single room fees

Travel insurance

optional

Some light meals

Day 1 (Travel Day) Departure for Milan

September 18 2026
Day 1 (Travel Day) Departure for Milan image

“What is the fatal charm of Italy? What do we find there that can be found nowhere else? I believe it is a certain permission to be human, which other places, other countries, lost long ago.” 

Erica Jong

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Departure from the USA to Milano

 Airfare not included...

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Uni-World/Jetaway Travel

In conjunction with Uniworld Travel (Endicott, NY), Keyrow Tours is pleased to make all flight arrangements, including primary flights originating from anywhere in the United States and international flights. We will depart from a major international airport located on the east coast of the United States [usually JFK (NY) or Philadelphia (PA)] and fly into Florence, Italy with one international layover. Transportation to and from your primary airport of departure is each person’s responsibility.

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The Team: Tour Director Paolo Carman

Paolo Carman is the founder, owner and director of Keyrow Tours, a family-run company which offers creative excursions for intimate sized groups.

Paolo has earned post-graduate degrees in Spirituality and Canon Law from the University of St. Thomas Aquinas in Rome (Italy). Having worked for the Vatican's Scavi Office for over 25 years, he shared the extraordinary archeological excavations beneath St. Peter's Basilica with guests from all over the world. Paolo has traveled extensively through 27 countries on 5 continents, and is now thrilled to pass on his love of history, cuisine and culture by hosting Keyrow guests in regions throughout Italy. He makes his home in a Central NY farmhouse dating back to the Civil War, along with his wife, Heather, the kitten gang and a host of native wildlife. Facilitating a powerful and transformational experience for Keyrow guests is a continuation of his lifelong commitment to serving others.

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Day 2 (Varenna) The Lake Escape

September 19 2026
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“Our battered suitcases were piled on the sidewalk again; we had longer ways to go. But no matter, the road is life.” 

Jack Kerouac

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Arrival in Miano

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Weather Information

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Private Transfer from Milan Airport to Lake Como

After arriving in Milan, we will set off by private minivan to Varenna, a historic village nestled on the eastern shore of Lake Como. Founded in the 8th century by fishing communities, Varenna flourished during the Middle Ages as a strategic trading post along the lake. Its brightly colored houses and cobblestone streets, preserved through centuries, speak to its rich past. For the next three nights, we will stay on the shores of Lake Como, a region that has been a retreat for the wealthy since Roman times and later a favored destination for Renaissance nobles. Our accommodations, offering panoramic views of the lake, will provide the perfect vantage point to connect with the history, charm, and serenity that have made this area an enduring jewel of Italy. 

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Arrival to Lake Como, hotel check-in and lunch

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Pranzo! (Lunch)

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Afternoon private boat departure for Bellagio and Villa Melzi’s botanical gardens

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Bellagio

Our group will arrive in Bellagio, a gem nestled at the meeting point of Lake Como’s three shimmering branches. As we stroll through the cobblestone streets, it will become clear why this enchanting village has drawn travelers for centuries. Perched at the tip of a peninsula, Bellagio has long been a haven for poets and aristocrats since the Renaissance, its elegant villas and gardens framed by the snow-capped Alps across the lake. The afternoon will be marked by the gentle breva breeze, cooling us as we soak in the beauty of this timeless lakeside retreat.

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Wine Tasting and Dinner on Bellagio

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Private boat transfer back to Varenna

Day's Recap: Reflection by

Keyrow Tours coordinates the ambiance and the magic of travel. However, YOU are the travelers soaking in the experience. You become the experts! 

Each evening, a few guests will be asked to present a brief reflection: there is no right or wrong with your reflection.

This could be something simple like sharing what your favorite observation was from earlier in the day. Previous Keyrow travelers have read passages from books, shared prior travel memories, created custom poems, and offered personal thoughts on their life's journey…the possibilities are endless!

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Overnight in Varenna

Day 3 (Varenna) Bellagio and Beyond

September 20 2026
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“Open my heart and you will see, Graved inside of it, Italy.” 

Robert Browning

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Weather Information

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Colazione! (Breakfast)

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Optional morning hike to Varenna’s Castle Vezio

Time9:30 AM
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Free time to explore Varenna

Our group will have the opportunity to enjoy free time in the charming village of Varenna, a peaceful haven along the shores of Lake Como. For centuries, this lake has been a retreat for Roman patricians and Renaissance nobles, drawn by its serene beauty and cultural treasures. Varenna itself is steeped in history, with its roots as a medieval fishing village. Strolling through its quiet streets, we’ll admire the traditional stone houses and vibrant lakeside promenades. For those seeking adventure, nearby villas like Villa Serbelloni and Villa Carlotta—adorned with exquisite gardens and art collections—tell stories of the aristocrats who once graced these shores. With the Alps as a breathtaking backdrop, the tranquility of the lake will offer a perfect respite before continuing our journey.

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Pranzo! (Lunch on your own)

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Private boat tour of the lake, with tour of Villa Balbianello

Time02:30 pm

Our group will embark on a private boat tour across the glacial waters of Lake Como, renowned for its striking beauty and storied history. This 146-square-kilometer lake, shaped like an inverted "Y," has been a source of inspiration since Roman times and remains a retreat for the world’s elite. As we glide past picturesque villages like Bellagio, Menaggio, and Varenna—situated at the intersection of the lake’s three branches—we will be surrounded by breathtaking views of the Alps and lush, forested slopes.

A highlight of our journey will be a visit to the historic Villa Balbianello. Perched on a wooded promontory near Lenno, this iconic villa was built in the late 18th century by Cardinal Angelo Maria Durini. Over the centuries, it has hosted adventurers, writers, and even served as a filming location for movies such as Casino Royale and Star Wars: Episode II. Surrounded by terraced gardens and offering panoramic views of the lake, the villa will give us a glimpse into the luxurious lives of those who called this enchanting region home.

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1. FAI - Villa Del Balbianello

Via Comoedia 5, Lenno, COMO, IT, 22016

Day's Recap: Reflection by

Keyrow Tours coordinates the ambiance and the magic of travel. However, YOU are the travelers soaking in the experience. You become the experts! 

Each evening, a few guests will be asked to present a brief reflection: there is no right or wrong with your reflection.

This could be something simple like sharing what your favorite observation was from earlier in the day. Previous Keyrow travelers have read passages from books, shared prior travel memories, created custom poems, and offered personal thoughts on their life's journey…the possibilities are endless!

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Cena! (Dinner)

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Overnight in Varenna

Day 4 (Varenna) Saint Moritz, Switzerland

September 21 2026
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“What a wonder it is! So grand, so solemn, so vast! And yet so delicate, so airy, so graceful! A varied world of solid weight, and yet is seems…a delusion of frostwork that might vanish with a breath!”

Mark Twain, describing the Cathedral of Milan

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Weather Information

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Weather Information

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Colazione! (Breakfast)

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Morning departure from Varenna by private minibus to Tirano, Italy

This morning our group will travel by private minibus through the stunning alpine landscapes to Tirano, a historic town nestled at the base of the Italian Alps. The journey will lead us past crystal-clear streams and through ancient forests, with snow-capped peaks rising dramatically in the distance. Tirano, known for its Renaissance-era basilica and its role as a crossroads for travelers since medieval times, offers a rich blend of history and natural beauty.

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Bernina Express Train from Tirano (Italy) to Saint Moritz (Switzerland)

Welcome aboard the legendary Bernina Express, a rail journey renowned for its unparalleled alpine scenery and engineering marvels. The train will wind its way from the warm, Mediterranean-influenced landscapes of northern Italy to the heart of the Swiss Alps. Highlights of the route include the spectacular Brusio spiral viaduct, an architectural feat dating back to 1908, and the Bernina Pass, which ascends to over 2,200 meters (7,200 feet) above sea level.

As we cross wild gorges, glide past ancient glaciers, and navigate looped tunnels, the sweeping views will captivate us at every turn. The train’s iconic red cars provide panoramic windows, perfect for capturing the pristine beauty of alpine valleys, sparkling lakes, and cascading waterfalls. Upon arriving in St. Moritz, the world-famous resort town known for its elegance and winter sports legacy, we’ll have time to explore its chic boutiques, sample its renowned chocolates, or simply soak in its alpine charm.

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Pranzo! (Lunch on your own)

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Private Minibus back to Varenna

Day's Recap: Reflection by

Keyrow Tours coordinates the ambiance and the magic of travel. However, YOU are the travelers soaking in the experience. You become the experts! 

Each evening, a few guests will be asked to present a brief reflection: there is no right or wrong with your reflection.

This could be something simple like sharing what your favorite observation was from earlier in the day. Previous Keyrow travelers have read passages from books, shared prior travel memories, created custom poems, and offered personal thoughts on their life's journey…the possibilities are endless!

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Cena! (Dinner)

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Overnight in Varenna

(Varenna) Magnificent Milano

Sep 22
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A Full Day Trip to Milano

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Day 5 (Monterosso) Cinque Terre Bound!

September 23 2026
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“Thou paradise of exiles, Italy!”

Percy Shelley

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Weather Information

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Colazione! (Breakfast)

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Morning minivan departure for Cinque Terre

Private minivans will take us from Lake Como to Cinque Terre’s village of Monterosso al Mare.

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Cinque Terre

Our group will journey to the captivating Cinque Terre, a rugged coastal treasure that has drawn visitors for centuries and earned UNESCO World Heritage status in 1997. The “Five Lands”—Monterosso, Vernazza, Corniglia, Manarola, and Riomaggiore—date back to at least the 11th century, when fishing and agriculture shaped their beginnings. Over generations, residents ingeniously constructed terraces into the steep cliffs to grow grapes and olives, leaving a legacy of sustainable living that endures today. Once accessible only by sea or narrow footpaths, these villages remained isolated until the 19th century, when a railway connected them to the wider world. Cars are still a rarity here, ensuring a peaceful retreat as we explore the winding paths, historic harbors, and timeless beauty of this coastal gem.

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Pranzo! (Lunch)

Food in Liguria is a celebration of local flavors and time-honored traditions. Anchovies (accuighe), freshly caught from the Ligurian Sea, are a cornerstone of the region’s cuisine, with dishes like tegame alla Vernazza blending anchovies, potatoes, tomatoes, white wine, and herbs into a savory delight. Pesto, born in this very region, has been perfected through centuries; basil thrives in the mild climate and is blended with Parmigiano, pecorino, garlic, olive oil, and pine nuts. Served over trofie, pasta designed specifically for pesto, it offers an authentic taste of Ligurian heritage. For something heartier, pansotti, ricotta and spinach ravioli paired with walnut sauce, is a local favorite. On the simpler side, farinata, a chickpea flatbread baked in wood-fired ovens, harkens back to humble peasant roots. And for a sweet finale, sciacchetrà wine, crafted from semi-dried grapes, offers a taste of Ligurian history in every golden drop.

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Boat or train to Riomaggiore and Manarola

Depending on the season and weather, we will navigate Cinque Terre by public boats or the local train system, each offering a unique perspective on this coastal paradise. If the weather allows, the boats will provide a leisurely journey along the rugged coastline, with panoramic views of the brightly colored villages clinging to the cliffs. Alternatively, the train will whisk us efficiently through tunnels carved into the mountains, a marvel of 19th-century engineering that connected these once-isolated villages to the world. Whether by water or rail, our journey will highlight the dramatic beauty of this UNESCO-protected region.

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Riomaggiore and the Via Del Amore

Riomaggiore, the southernmost village of the Cinque Terre, sits tucked into a narrow valley where the "Rivus Maior" river once flowed, giving the village its name. According to legend, this picturesque hamlet was founded in the 8th century by Greek refugees seeking safety along the Ligurian coast. The village's most famous feature, the Via dell’Amore ("Lover’s Way"), is a cliffside path carved into the rock in the early 20th century. Originally built to connect Riomaggiore to Manarola for workers on the railway, it now serves as a romantic promenade offering sweeping views of the turquoise sea and dramatic cliffs.

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Manarola

Manarola, thought to be the oldest village in the Cinque Terre, carries a deep sense of history and charm. The Church of San Lorenzo, whose cornerstone dates back to 1338, stands as a testament to the town’s medieval roots. The village’s name is believed to have evolved from the Latin magna rota, meaning "large wheel," a nod to the ancient mill wheel that once played a vital role in the town’s daily life. Today, Manarola enchants visitors with its vibrant, pastel-colored houses perched on steep cliffs overlooking the sea. The terraced vineyards surrounding the village produce the renowned Sciacchetrà, a sweet wine that has been crafted here for centuries. During the holiday season, Manarola transforms into a spectacle of lights, showcasing the world’s largest nativity scene, a tradition that reflects the village’s rich cultural heritage.

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Back to Monterosso

Day's Recap: Reflection by

Keyrow Tours coordinates the ambiance and the magic of travel. However, YOU are the travelers soaking in the experience. You become the experts! 

Each evening, a few guests will be asked to present a brief reflection: there is no right or wrong with your reflection.

This could be something simple like sharing what your favorite observation was from earlier in the day. Previous Keyrow travelers have read passages from books, shared prior travel memories, created custom poems, and offered personal thoughts on their life's journey…the possibilities are endless!

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Cena! (Dinner)

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Overnight in Monterosso

Day 6 (Monterosso) Life on the Ligurian Sea

September 24 2026
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“For us to go to Italy and to penetrate into Italy is like a most fascinating act of self-discovery – back, back down the old ways of time. Strange and wonderful chords awake in us, and vibrate again after many hundreds of years of complete forgetfulness.”

D.H. Lawrence

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Weather Information

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Colazione! (Breakfast)

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Free Day in the Cinque Terre

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Optional Morning Hike: Corniglia to Vernazza

For those seeking adventure, a morning hike from Corniglia to Vernazza offers a chance to experience Cinque Terre’s dramatic landscapes up close. This 2.5-hour trek follows an ancient goat path, historically used by villagers to connect these cliffside towns. With a difficulty level of 3 out of 4, it’s a rewarding challenge that winds through terraced vineyards, fragrant Mediterranean vegetation, and rocky overlooks offering breathtaking views of the Ligurian Sea.

For those preferring a more leisurely morning, train to Vernazza! Its charming streets, local shops, and tranquil atmosphere provide plenty to explore. At the end of the hike, hikers and non-hikers alike will reunite in Monterosso for dinner, ready to share stories and enjoy the beauty of this iconic village.

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Recommended Explorations

Embark on your own a journey through the stunning villages of Cinque Terre by ferry, train, and foot, each offering a unique perspective on this UNESCO World Heritage site. Start with a public ferry or train from Monterosso al Mare to Vernazza. Enjoy leisure time in the shops, sip vino, and watch the world go by...

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Pranzo! (Lunch on your own)

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The beauty of Monterosso al Mare...

The ancient, original centre of Monterosso lies on the summit of the hill of San Cristoforo, which separates the present village into two. During the 12th and 13th century there was an increase in population and families began to move down the slope of the hill, setting up house on the banks of the stream called “Branco” which is now covered. This part of the village, known as Monterosso Vecchio (Old Monterosso), has remained practically intact from that time period. Monterosso's beach is the longest of the Cinque Terre coast and the “carruggi” (small streets) of Old Monterosso are picturesque gems from a different time period…

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Day's Recap: Reflection by

Keyrow Tours coordinates the ambiance and the magic of travel. However, YOU are the travelers soaking in the experience. You become the experts! 

Each evening, a few guests will be asked to present a brief reflection: there is no right or wrong with your reflection.

This could be something simple like sharing what your favorite observation was from earlier in the day. Previous Keyrow travelers have read passages from books, shared prior travel memories, created custom poems, and offered personal thoughts on their life's journey…the possibilities are endless!

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Cena! (Dinner)

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Overnight in Monterosso

Day 7 (Bologna) Bella Bologna

September 25 2026
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“All journeys have destinations of which the traveler is unaware.”  

Martin Buber

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Weather Information

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Colazione! (Breakfast)

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Transfer from Cinque Terre to Bologna

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Bologna

Bologna, the vibrant capital of the Emilia-Romagna region, is a city where ancient history meets modern vitality. With roots stretching back over a millennium before the Common Era, it was first settled by the Etruscans, later occupied by the Celts, and eventually flourished under Roman rule. During the Middle Ages, Bologna cemented its intellectual legacy as the birthplace of the world’s oldest university, founded in 1088. Even today, the University of Bologna attracts thousands of students who infuse the city with youthful energy and cultural diversity.

Famous for its medieval towers and the world’s longest network of porticoes, Bologna’s historic center is remarkably well-preserved, offering a window into its storied past. Beyond its architecture, Bologna is a culinary treasure, often celebrated as the gastronomic capital of Italy. Known for its high quality of life, the city is both a haven for history enthusiasts and a bustling hub of culture and innovation.

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Arrival to hotel

Time to unpack and get settled

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Pranzo! (Lunch)

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Private Guided Walking Tour

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Bologna's Treasures...

At the heart of Bologna lies Piazza Maggiore, the city’s central plaza and a bustling hub of activity since the 13th century. Originally established as a marketplace and gathering space, it remains a cherished meeting point for locals today. Dominated by the iconic Fountain of Neptune and framed by the grandeur of the Basilica of San Petronio, this piazza embodies Bologna’s rich medieval heritage. The Basilica, dedicated to the city’s patron saint, is a striking example of Italian Gothic architecture, its unfinished façade a reminder of ambitions left incomplete.

Surrounding Piazza Maggiore are some of Bologna’s most significant historical landmarks. We will explore the Palazzo del Podestà, a 13th-century palace of government; the Basilica of San Petronio; and the haunting World War II Memorial. Nearby, the University of Bologna’s Anatomical Theater offers a glimpse into 17th-century medical education with its public autopsies, while Santa Maria della Vita houses the dramatic “Screaming Marys” terracotta sculptures depicting the death of Jesus. Rounding out our visit, we’ll marvel at Bologna’s famous Two Leaning Towers and the serene Basilica of Santo Stefano. Each step in and around Piazza Maggiore reveals layers of history and culture in this remarkable city.

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Day's Recap: Reflection by

Keyrow Tours coordinates the ambiance and the magic of travel. However, YOU are the travelers soaking in the experience. You become the experts! 

Each evening, a few guests will be asked to present a brief reflection: there is no right or wrong with your reflection.

This could be something simple like sharing what your favorite observation was from earlier in the day. Previous Keyrow travelers have read passages from books, shared prior travel memories, created custom poems, and offered personal thoughts on their life's journey…the possibilities are endless!

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Cena! (Dinner)

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Overnight in Bologna

Day 8 (Bologna) Di-Vine Wanderings

September 26 2026
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"Life for the Italians was what it was, no more and no less, an interlude between meals."

Abraham Verghese in "Cutting for Stone"

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Colazione! (Breakfast)

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Morning departure for the Emilia–Romagna countryside

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A Foodie's Delight!

Today we embark upon an epicurean adventure, visiting and tasting some of the most important edible elements that the local culture celebrates and provides...

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Parmigiano Reggiano Cheese Factory

Our journey will take us by private coach from Bologna to a renowned Parmigiano Reggiano cheese farm, where we will witness the art and tradition behind one of Italy’s most iconic products. Known as the “King of Cheeses,” Parmigiano Reggiano has been crafted in this region for over 800 years, using time-honored techniques passed down through generations.

During our visit, we’ll follow the intricate production process, from the fresh milk collected daily to the careful shaping and salting of the wheels. In the aging rooms, where the cheese develops its distinct flavor over months or even years, we’ll have the opportunity to sample this culinary treasure. As we taste, we’ll gain a deeper appreciation for the craftsmanship and dedication that make Parmigiano Reggiano a symbol of excellence worldwide.

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Balsamic Vinegar Production

After our visit to the cheese farm, we will continue to a private villa where the art of traditional balsamic vinegar production comes to life. Here, we will taste new and aged vinegars, each offering a unique depth of flavor. Known as Aceto Balsamico Tradizionale, this treasured condiment has been crafted in Modena and Reggio Emilia since the Middle Ages, with its production first documented in 1046 when a bottle was gifted to Emperor Henry III.

Unlike common vinegar, traditional balsamic vinegar is made from the reduction of cooked Trebbiano grape juice, aged slowly in wooden barrels, and prized for its complex, syrupy sweetness. The term balsamico, derived from Latin and Greek roots meaning "restorative" or "curative," reflects its historical use not only as a culinary delight but also for its medicinal qualities. This visit will provide a sensory journey into one of Italy’s most cherished gastronomic traditions.

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Prosciutto Production

We will visit a traditional prosciutto production facility to witness the time-honored process of curing this world-renowned delicacy. Using only select cuts of pork and sea salt, artisans have perfected the method over centuries, creating the rich, savory flavors that make Italian prosciutto a culinary treasure.

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Pranzo! (Lunch)

We will dine well as a perfect end to a day filled with the very best of local food culture.

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Back to Bologna

Day's Recap: Reflection by

Keyrow Tours coordinates the ambiance and the magic of travel. However, YOU are the travelers soaking in the experience. You become the experts! 

Each evening, a few guests will be asked to present a brief reflection: there is no right or wrong with your reflection.

This could be something simple like sharing what your favorite observation was from earlier in the day. Previous Keyrow travelers have read passages from books, shared prior travel memories, created custom poems, and offered personal thoughts on their life's journey…the possibilities are endless!

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Cena! (Dinner)

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Overnight in Bologna

Day 9 (Tuscany) Life in the Tuscan Hills

September 27 2026
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“Wherever you go becomes a part of you somehow”

– Anita Desai

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Weather Information

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Private Transfer from Bologna to Tuscany

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Check into Our Tuscan Villa

We are delighted to welcome you to the rolling hills and enchanting countryside of Tuscany, where life’s simple pleasures are celebrated with elegance and style.

Our home for this unforgettable journey is a luxurious private villa perfectly situated in a peaceful and secluded setting. This villa will be our sanctuary as we explore, unwind, and immerse ourselves in the timeless beauty of Tuscany.

The villa’s estate comprises three thoughtfully designed structures:

  • The Main Guest House: Featuring five beautifully appointed bedrooms, each with a private bathroom, and shared spaces including a dining room, breakfast room, fully equipped kitchen, and a cozy billiards room. Outdoors, you’ll find an infinity swimming pool and inviting seating areas perfect for relaxation. All villa meals will be hosted in this central space.
  • The Cottage Suite: Located just a few steps from the main house, this two-story building offers two bedrooms with bathrooms upstairs and a shared family room with a TV and kitchenette downstairs.
  • The Fitness Center: A serene space equipped with a small workout area and a sauna for ultimate relaxation.

Please note that room assignments are made randomly, though we strive to keep families and friends close together. All accommodations at the villa are designed to provide comfort, privacy, and a restful retreat after our days exploring Tuscany’s treasures.

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Mid-afternoon at villa

Welcome to the picturesque hills of Tuscany, a region celebrated for its timeless landscapes and deep historical roots dating back to the Etruscans, who first cultivated these lands over 2,500 years ago. Our home for the next six nights is a private Tuscan villa, nestled in a serene and secluded setting surrounded by rolling vineyards and olive groves that have been a hallmark of the region since antiquity.

This villa will be our haven, offering a perfect balance of relaxation and exploration. In the afternoon, unwind by the infinity pool, enjoy the villa’s welcoming common spaces, or simply take in the breathtaking views of the countryside. This tranquil retreat allows us to connect with Tuscany’s rich heritage and indulge in its enduring beauty.

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Orientation with time to relax and explore our new surroundings

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Pranzo! Light lunch and drinks provided

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Visit to Torre a Cona Winery for tour and tasting

We will visit a historic winery set amidst the scenic Tuscan hills. With roots dating back to the 18th century, this estate blends tradition and innovation, offering a guided tour through its vineyards and cellars, followed by a tasting of its exceptional wines crafted from centuries-old practices.

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Day's Recap: Reflection by

Keyrow Tours coordinates the ambiance and the magic of travel. However, YOU are the travelers soaking in the experience. You become the experts! 

Each evening, a few guests will be asked to present a brief reflection: there is no right or wrong with your reflection.

This could be something simple like sharing what your favorite observation was from earlier in the day. Previous Keyrow travelers have read passages from books, shared prior travel memories, created custom poems, and offered personal thoughts on their life's journey…the possibilities are endless!

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Cena! (Dinner)

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Overnight in Tuscan Villa

Day 10 (Tuscany) Medieval Time Travel in Siena

September 28 2026
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“Traveling forces you to lose sight of all the familiar comforts of home. Nothing is yours except the essential things – air, sleep, dreams, the sea, the sky – all things tending towards the eternal or what we imagine of it.”  

Cesare Pavese

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Weather Information

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Colazione! (Breakfast)

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Private transfer to Siena

Departure09:00 am
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Private Guided Walking Tour: Meet Costanza

My name is Costanza, and I will serve as your local city guide today. I was born in Siena and raised in a nearby village in the Tuscan countryside. I have a degree in Natural Sciences and have lived in Siena all my life, except one year that I spent in England where I was doing a research in a National Park.

Siena is so rich in history and traditions that I decided to further my education by studying art history and archaeology. I love to talk about every aspect of this place that I call "my home": its nature, art, history, local traditions, cuisine and good wines. Shall we explore it all together?

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Siena

Our journey will take us to Siena, a city steeped in history and legend, whose UNESCO-listed historic center preserves the essence of medieval Italy. First settled during the Etruscan era (c. 900–400 BC), Siena grew into a powerful medieval city-state renowned for its art, cuisine, and the famed Palio, a thrilling horse race held twice a year in the heart of the city’s Piazza del Campo.

According to local lore, Siena’s origins are tied to Senius and Aschius, the sons of Remus and nephews of Romulus, who founded Rome. Fleeing after their father’s murder, they brought with them the iconic symbol of the she-wolf nursing twins, a motif that remains central to the city’s identity.

Siena is also the birthplace of Saint Catherine, a revered mystic and poet whose writings and devotion made her one of the most influential figures of her time. Over lunch, we’ll delve into her life, including her poetic depiction of God as an “inebriated lover,” and toast to the enduring spirit of this remarkable city.

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Pranzo! (Lunch)

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Personal time in Siena

Enjoy personal time to wander through Siena’s enchanting medieval streets Explore the iconic Piazza del Campo, visit boutique shops, or simply relax in a café while soaking in the city’s rich history and vibrant atmosphere.

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Return to our villa

Day's Recap: Reflection by

Keyrow Tours coordinates the ambiance and the magic of travel. However, YOU are the travelers soaking in the experience. You become the experts! 

Each evening, a few guests will be asked to present a brief reflection: there is no right or wrong with your reflection.

This could be something simple like sharing what your favorite observation was from earlier in the day. Previous Keyrow travelers have read passages from books, shared prior travel memories, created custom poems, and offered personal thoughts on their life's journey…the possibilities are endless!

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Cena! (Dinner)

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Overnight in Tuscan Villa

Day 11 (Tuscany) Noble Wine and Nibbles

September 29, 2026
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“A journey is best measured in friends, not in miles”

– Tim Cahill

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Weather Information

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Colazione! (Breakfast)

Private transfer to Montepulciano

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Montepulciano

Montepulciano, a stunning Tuscan hill town, combines centuries of history with breathtaking views and renowned wines. Built along the ridge of Monte Poliziano, this village has roots as a fortified settlement dating back to 715, later flourishing during the Renaissance. Its cobbled main street stretches 11.5 kilometers, leading visitors past historic landmarks to the grand Piazza Grande, where the cathedral, completed in 1619, stands as a centerpiece of architectural elegance. The town also served as a strategic outpost during the struggles between Florence and Siena in the Middle Ages, with its fortifications playing a key role in regional conflicts.

Known worldwide for its exceptional wines, Montepulciano offers a chance to taste the celebrated Vino Nobile di Montepulciano and Rosso di Montepulciano. As you explore, you’ll uncover a town that weaves together its rich past, scenic beauty, and winemaking traditions into an unforgettable experience.

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Visit to Gattavecchi Winery for lunch and tasting

Time1:00 PM
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Pienza

Perched between Montepulciano and Montalcino, the village of Pienza is a Renaissance masterpiece with a playful side. Originally known as Corsignano, this modest village was transformed in the 15th century by Pope Pius II, who sought to create an “ideal city” that embodied humanist ideals of balance and beauty. Designed by architect Bernardo Rossellino, Pienza became a model for Renaissance urban planning and remains a UNESCO World Heritage Site for its harmonious layout and architectural significance.

Beyond its historical grandeur, Pienza has a cheesy claim to fame. Renowned for its Pecorino, made from the milk of sheep grazing the local pastures, this town celebrates its culinary pride with an annual Pecorino tossing contest—a tradition as lively as it is delicious. As we wander through its charming streets and sample its famous cheese, we’ll experience a town that blends history, flavor, and fun in perfect harmony. Pass the Pecorino, per favore!

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Transfer back to the villa

Day's Recap: Reflection by

Keyrow Tours coordinates the ambiance and the magic of travel. However, YOU are the travelers soaking in the experience. You become the experts! 

Each evening, a few guests will be asked to present a brief reflection: there is no right or wrong with your reflection.

This could be something simple like sharing what your favorite observation was from earlier in the day. Previous Keyrow travelers have read passages from books, shared prior travel memories, created custom poems, and offered personal thoughts on their life's journey…the possibilities are endless!

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Cena! (Dinner)

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Overnight in Tuscan Villa

Day 12 (Tuscany) Florence… Fantastico!

September 30, 2026
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“To awaken quite alone in a strange town is one of the most pleasant sensations in the world. You are surrounded by adventure” 

– Freya Stark

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Weather Information

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Colazione! (Breakfast)

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Private Transfer to Florence

Departure08:15 am
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Private Guided Walking Tour: Meet Adriana

Adriana (Adri) Faust Bianchi was born to American and Italian parents in Florence, Italy. Early in her in career, she taught English and Italian for extended periods of time in Sweden and in Great Britain, where she feels very much at home. Adri has worked extensively in the luxury travel industry. She currently resides in Florence, and operates a successful business as a licensed tour guide in the Tuscan region, welcoming visitors from all over the world. A proud mother of two young adult daughters, Adri's passions include travel, hiking, horses, photography, Renaissance art and her beloved city of Florence. Adri has worked for Keyrow Tours for over a decade, making the enchanted vistas of Florence come alive for Keyrow guests. She has also expanded her role as a tour director for Keyrow Tours, hosting Italian adventures beyond the Tuscan sun.

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Ponte Vecchio

The Ponte Vecchio, or “Old Bridge,” is one of Florence’s most iconic landmarks and a symbol of the city’s enduring charm. Spanning the Arno River, this historic bridge dates back to 1345 and is renowned as the only Florentine bridge to survive World War II, allegedly spared by direct order of Hitler. Once home to butchers and tanners, the bridge was transformed in the 16th century by Duke Ferdinand I, who replaced the workshops with luxurious gold and jewelry shops—a tradition that continues today.

Conveniently located just steps from our hotel, the Ponte Vecchio offers not only a shopper’s paradise but also a stunning view of the Arno, making it a must-visit for both history enthusiasts and treasure seekers alike!

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Piazza Signoria

Piazza Signoria, Florence’s central square, has been the city’s political and cultural heart since the 14th century. The square witnessed pivotal moments in history, including the rise of the Medici family and the infamous Bonfire of the Vanities in 1497, when religious zealots destroyed art and luxury goods under the influence of the preacher Savonarola. 

The Palazzo Vecchio, originally built in 1299, stands as a testament to Florence’s power during the Renaissance and has been the seat of government since Medici rule. The Loggia dei Lanzi, an open-air gallery, features sculptures spanning centuries, including Benvenuto Cellini’s bronze masterpiece of Perseus holding Medusa’s severed head, a work commissioned by Duke Cosimo I in the 16th century to symbolize his triumph over tyranny.

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The Academia Museum

The Accademia Museum houses some of the most extraordinary works of Renaissance art, offering a window into Florence’s golden age. Its centerpiece, Michelangelo’s David, was carved from a single block of marble between 1501 and 1504 and originally intended to adorn the rooftop of the Florence Cathedral. The statue instead became a symbol of Florentine independence and was placed in Piazza Signoria before being moved indoors for preservation. Visitors will also encounter Michelangelo’s Prisoners, unfinished sculptures intended for Pope Julius II’s tomb, which illustrate the artist’s belief in "liberating the figure" from the stone. The museum provides a deeper understanding of the genius and innovation that flourished during the Renaissance.

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Pranzo! (Lunch)

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Late afternoon departure for dinner in our Tuscan villa

Day's Recap: Reflection by

Keyrow Tours coordinates the ambiance and the magic of travel. However, YOU are the travelers soaking in the experience. You become the experts! 

Each evening, a few guests will be asked to present a brief reflection: there is no right or wrong with your reflection.

This could be something simple like sharing what your favorite observation was from earlier in the day. Previous Keyrow travelers have read passages from books, shared prior travel memories, created custom poems, and offered personal thoughts on their life's journey…the possibilities are endless!

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Cena! (Dinner)

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Overnight in Tuscan Villa

Day 13 (Tuscany) Free Day in the Villa

October 1, 2026
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Free Day at the Villa

Take a day to unwind and embrace the tranquility of our Tuscan villa. Stroll through the picturesque countryside, where centuries-old olive groves and vineyards stretch as far as the eye can see, evoking the agricultural traditions of the region. Enjoy the villa’s luxurious amenities—lounge by the infinity pool or relax in the sauna. For some lighthearted fun, challenge a friend to a game of pool or ping pong, or simply find a quiet spot to savor a good book and a glass of local vino. This is a day to recharge and fully immerse yourself in the timeless beauty of Tuscany.

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Breakfast

Optional Massage Therapy

Book an optional massage with Keyrow Tours during your free day at the villa. You won't regret it!

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Pranzo (Lunch!)

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Private Tuscan Cooking Class at our Villa with dinner included

Welcome to the glorious hills and countryside of the Tuscany region, where simple pleasures are elevated to an art form. This afternoon, you'll take part in a hands-on cooking experience that celebrates the rich culinary traditions of the area. From fresh pasta to seasonal local ingredients, this will be an afternoon to remember as we honor the flavors and bounty of Tuscany.

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Cena (Dinner!)

Day's Recap: Reflection by

Keyrow Tours coordinates the ambiance and the magic of travel. However, YOU are the travelers soaking in the experience. You become the experts! 

Each evening, a few guests will be asked to present a brief reflection: there is no right or wrong with your reflection.

This could be something simple like sharing what your favorite observation was from earlier in the day. Previous Keyrow travelers have read passages from books, shared prior travel memories, created custom poems, and offered personal thoughts on their life's journey…the possibilities are endless!

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Overnight at the villa

Day 14 (Tuscany) Exploring Pisa and Lucca, Under the Tuscan Sun

October 2, 2026
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“As with circling round of turrets, Monteriggioni crowns his walls; E’en thus the shore, encompassing the abyss, Was turreted with giants, half their length Uprearing, horrible, whom Jove from heaven Yet threatens, when his muttering thunder rolls.”

Dante Alighieri, Hell, canto XXXI, lines 40-45

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Weather Information

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Colazione! (Breakfast)

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Morning departure for Pisa

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Pisa

Our small group of friends set out to explore the charming city of Pisa. Together we will marvel at the iconic Leaning Tower, and wander through its narrow streets that surround Piazza dei Miracoli and its beautiful cathedral. 

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Lucca

 Armed with curiosity and a map (and a local guide of course!), we will meander through cobblestone streets, marveling at ancient Roman ruins and medieval towers. Together we will listen to tales about the city's past rulers and famous landmarks. With each step, we will surely feel a deeper connection to Lucca's storied past, imagining the lives of those who once walked its historic walls. And the end of our tour we will gather in a cozy trattoria, toasting to today's journey through the layers of history that made Pisa and Lucca come alive before our eyes.

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Return to our villa

Day's Recap: Reflection by

Keyrow Tours coordinates the ambiance and the magic of travel. However, YOU are the travelers soaking in the experience. You become the experts! 

Each evening, a few guests will be asked to present a brief reflection: there is no right or wrong with your reflection.

This could be something simple like sharing what your favorite observation was from earlier in the day. Previous Keyrow travelers have read passages from books, shared prior travel memories, created custom poems, and offered personal thoughts on their life's journey…the possibilities are endless!

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Cena! (Dinner)

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Overnight in Tuscan Villa

Day 15 (Travel Day) Arrivederci Italia!

October 3, 2026
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“Travel does what good novelists also do to the life of the everyday, placing it like a picture in a frame or a gem in its setting, so that the intrinsic qualities are made more clear. Travel does this with the very stuff that everyday life is made of, giving to it the sharp contour and meaning of art.”

Freya Stark

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Colazione! (Breakfast)

Private transfer to Florence's Airport and return to the USA

Thank you so much for joining Keyrow Tours. Until next time, arrivederci! 

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Once Upon a Time...

Once upon a time, a small group of friends decided to embark on an unforgettable journey through Italy. Their first stop was the breathtaking Lake Como, where they spent peaceful mornings sipping espresso by the water and exploring the charming towns along the lake.

Next, they ventured to the colorful villages of Cinque Terre, where they hiked the scenic coastal trails and indulged in delicious seafood pasta at local trattorias. The group marveled at the stunning views of the Mediterranean Sea and watched the sunset over the rugged cliffs.

In Bologna, they immersed themselves in the rich gastronomic culture of the city, indulging in mouthwatering dishes like handmade tortellini and creamy gelato. They also explored the historic architecture of the city, visiting medieval towers and beautiful piazzas.

Their final destination was the rolling hills of Tuscany, where they stayed in a charming villa surrounded by vineyards and olive groves. They sampled world-renowned wines, visited medieval hilltop towns, and enjoyed leisurely strolls through the picturesque countryside.

They entered as strangers, and now they leave as friends. As their journey came to an end, these new friends reflected on the unforgettable experiences they shared and the deep bonds they had formed. They knew that their memories of exploring Northern Italy together would last a lifetime, and each individual vowed to embark on more adventures in the future...

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