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The Best of Tuscany April 2026

The Best of Tuscany April 2026 image

Welcome to Keyrow

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 visit the main attractions on all of our trips, but we especially love to explore off-the-beaten-path places that capture the essence of Italy and our imagination. 

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, Founder

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Overview

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Welcome to Keyrow

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1. Siena

53100 Siena, Province of Siena, Italy

2. Florence

Florence, Metropolitan City of Florence, Italy

3. Montepulciano

53045 Montepulciano, Province of Siena, Italy

4. Pienza

53026 Pienza, Province of Siena, Italy

5. Greve in Chianti

50022 Greve in Chianti, Metropolitan City of Florence, Italy

6. San Gimignano

53037 San Gimignano, Province of Siena, Italy

7. Pisa

Pisa, Province of Pisa, Italy

8. Lucca

55100 Lucca, Province of Lucca, Italy

Information & Documents

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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

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Movie Entertainment Before and After Your Trip

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Italian Words and Phrases

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: Departure for Tuscany

Apr 25
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“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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Enjoy seven nights in a fabulous private Tuscan villa....

Your home in the Tuscan hills is surrounded by olive orchards and vineyards. Complete with a swimming pool, private chef and butler... this is a perfect short getaway or launching point to explore more of Italy on your own!

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Information

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: (San Donato) Life in the Tuscan Hills

Apr 26
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“Wherever you go becomes a part of you somehow”

– Anita Desai

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Information

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Flight arrival into Rome's Leonardo da Vinci Airport

After passport control and collecting our luggage, private minivans will carry us to our private Tuscan villa…

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Private transfer to Tuscany: First Stop, Lunch at a Winery!

3 minivans... included

Because our rooms will not be ready this early, we will travel from the airport directly to lunch at a neighboring winery. Nothing better that hitting the ground running with a little wine tasting! :)

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Visit to the neighboring Fattoria Torre e Cona Winery for lunch and tasting

Time1:30 PM

Appetizer: Vegetable flan with a light cheese sauce 

First course: Ricotta and spinach gnudi pasta with butter and sage, topped with cheese shavings 

 Dessert: Chocolate cake

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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, Villa di Paolo 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 two 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, and fully equipped kitchen. Outdoors, you’ll find a 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 building offers two bedrooms with bathrooms and a shared family room with a TV and kitchenette downstairs.

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 glorious hills and countryside of the Tuscany Region, where simple pleasures are elevated to an art form. Our home for the next six nights is a beautiful private Tuscan villa, situated in a charming and secluded setting. Our villa will be an oasis as we explore, celebrate and enjoy the bounty of Tuscany.

These are some images of our actual villa...

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More Images of our Private Tuscan Villa....

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Orientation with time to relax and explore our new surroundings

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Cena! (Dinner in the Villa, included)

Time7:00 PM

DINNER AT THE VILLA

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Overnight in Tuscan Villa

Day 3: (San Donato) Medieval Time Travel in Siena

Apr 27
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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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Colazione! (Breakfast)

Time7:30 AM

BREAKFAST AT THE VILLA

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Departure for Siena

Time9:00 AM
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Siena

The historic center of Siena has been declared by UNESCO a World Heritage Site. It is one of the nation's most visited attractions, and is famous for its cuisine, art, museums, medieval cityscape and the Palio, a horse race that is held twice a year. 

Siena, like other Tuscan hill towns, was first settled in the time of the Etruscans (c. 900– 400 BC).

According to local legend, Siena was founded by Senius and Aschius, two sons of Remus and thus the nephews of Romulus, after whom Rome was named. Legend has it that after their father was murdered by Romulus, they fled Rome, taking with them the statue of the she-wolf suckling the infants and appropriating that symbol for the town. 

The most famous daughter of this important medieval city is Saint Catherine of Siena: a medieval mystic, poet and feminist-figure of her time. We will learn about Saint Catherine over lunch… and why she referred to God as an “inebriated lover.” Cheers!  

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Private Guided Walking Tour: Meet our guide Costanza Riccardi

Duration3 hours
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Pranzo! (Lunch on your own)

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Personal time in Siena

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Return to our villa

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Cena! (Dinner included)

Time7:00 PM

HAPPY HOUR/DINNER AT THE VILLA

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Overnight in Tuscan Villa

Day 4: (San Donato) Florence… Fantastico!

Apr 28
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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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Colazione! (Breakfast)

Time7:30 AM

BREAKFAST AT THE VILLA

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Morning departure for Florence

Time8:30 AM
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Private Guided Walking Tour of Florence

Time9:15 AM

Guide, Tickets and gratuity included.

MEETING POINT: Piazza Republica at the Hotel Savoy

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Private Guided Walking Tour: Meet Adri

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 looks forward to expanding her role to include hosting new adventures beyond the Tuscan sun.

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Ponte Vecchio

Ponte Vecchio, translated, means “The Old Bridge.” This historic bridge that crosses the Arno River is laden with gold and diamond shops. Conveniently located just around the corner from our hotel, shoppers…this one’s for you!

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Piazza Signoria

This is Florence’s central square. See the Palazzo Signoria (Florence’s City Hall since the reign of the Medici’s), the outdoor Loggia contains ancient Roman, Greek and Renaissance statuary, including Celini’s famous bronze of Persius holding Medusa’s severed head.

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The Duomo Cathedral (Exterior)

Built in the Middle Ages, the original architects left it uncompleted in a sheer act of faith: a large hole in its roof awaited a dome long before the technology existed to span such a distance. No Problema! Brunelleschi’s dome eventually completed the structure, becoming Michelangelo’s model for St. Peter’s Basilica in the Vatican and the model for the future U.S. Capitol.

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Florence’s Accademia Museum

Time11:30 AM

Enjoy incredible Renaissance artwork including Michelangelo’s monolithic statue of David and his famous series of “Prisoners” designed for Pope Julius II’s tomb in Rome

TICKETS WILL APPEAR HERE:

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Pranzo! (Lunch included)

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Mid to late Afternoon departure for the villa

Time4:30 PM

Where are we going for dinner? "Follow Paolo!"

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Cena! (Dinner included)

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Overnight in Tuscan Villa

Day 5: (San Donato) Free Day in the Villa

Apr 29
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Breakfast

Time7:30 AM
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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 pool 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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Pranzo (Lunch included)

Time12:00 PM
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Optional Massage Therapy Sessions

70 euros per hour to be pre-paid directly to Paolo. 


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Optional Biscotti Making Class!

Time2:00 PM
Duration1 hour 30 Minutes

My name is Elisa and I am 30 years old. I was born and raised in Florence, with two lovely parents and a younger sister. You may have met my mom Adri, your guide in Florence! As a baker and pastry cook, experience in high level restaurants and hotels has taught me to be determined to learn and discover more. Join me (and my passion for food), all in the comfort of my own kitchen.. Together we will make biscotti!!!

Price dependent on participants

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Private Tuscan Cooking Class at our Villa with dinner

Time4:00 PM

In the glorious hills and countryside of the Tuscany Region, simple pleasures are elevated to an art form. This afternoon we cook with a local chef and celebrate the bounty of Tuscany!

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Overnight in Tuscan Villa

Day 6: (San Donato) Noble Wine and Nibbles

Apr 30
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“A journey is best measured in friends, not in miles”

– Tim Cahill

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Colazione! (Breakfast)

Time7:30 AM

BREAKFAST AT THE VILLA

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Departure for Montepulciano

Departure9:00 AM
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Montepulciano

The Medieval and Renaissance village of Montepulciano is one of the most attractive hills towns in Tuscany. It is built on the ridge of Monte Poliziano, and its main street stretches for 11.5 kilometers from the Porta al Prato to the Piazza Grande at the top of the hill. The cathedral was built in 1619, and the castle of Montepulciano was first mentioned as a fortified center in the year 715. Of course Montepulciano is famous for not just one, but two excellent wines: Vino Nobile di Montepulciano and Rosso di Montepulciano. For those who partake in the fruit of the vine, you will have the opportunity to try both!

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Pranzo! (Lunch at a winery, included)

Gatavecchi
Time1:30 PM

Bruschetta Selection

Pici pasta with Garlic

Pork Loin with Baked Potatoes

Cantucci and Vino Santo

Tasting of 3 wines: Rosso di Montepulciano, Nobile di Montepulciano, Riserva

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Pienza

Nestled between the towns of Montepulciano and Montalcino, this small village was rebuilt by Pope Pius II who was born there, as the ideal Renaissance city and as a retreat for the Pope from Rome. It produces some of the best Pecorino cheese in the world which we will sample! Pienza is known for its annual Pecorino tossing contest. Pass the Pecorino, per favore!

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Cena! (Dinner included)

Lunch was huge today! 

The chef will leave soup and salad for you to prepare for yourselves... We will kindly clean up afterwards.


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Overnight in Tuscan Villa

Day 7: (San Donato) The Chianti Region

May 01
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Colazione! (Breakfast)

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Private Transfers for the whole day

Departure9:00 AM
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World War II American Cemetery

Just outside Florence, we will offer our respects to over 4,000 American service men and women who paid the ultimate price during the Second World War.

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Greve in Chianti

Explore this quaint Tuscan village

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Torciano wine tasting school and lunch

Tenuta Torciano has been producing wine and olive oil since 1720, a tradition passed down through generations of the Giachi family. With its panoramic views of rolling hillsides, vineyards, and olive groves, this estate offers an idyllic setting. A family member will guide us through the art of wine making and the science of wine tasting and pairing. Enjoy a sumptuous luncheon featuring local, organic ingredients, offering a true taste of Tuscany’s culinary heritage. Buon appetito...

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San Gimignano

San Gimignano is known as the “Manhattan of Tuscany” because of its many medieval towers that look like skyscrapers from a distance. 15 minutes from Tenuta Torciano, this is a charming town. Visit its central square, stroll into numerous shops, or dare to walk into the Medieval Torture Museum…we will have about two hours to enjoy this gem in the heart of Tuscany. Sample some wild boar meat while you’re here!

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Cena! (Dinner)

Day 8: (San Donato) Under the Tuscan Sun

May 02
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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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Colazione! (Breakfast)

Time7:30 AM

BREAKFAST AT THE VILLA

Private Transfer included

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Departure for Pisa

Time9:00 AM

Pisa is a legendary city and one of the most famous in this region of Italy. Located on the western coast of Italy, Pisa is only 20 minutes from the Ligurian Sea and has great transport links to Florence, Livorno and La Spezia. 

During the 11th century and onwards Pisa rose to prominence and became one of the major maritime republics of Italy. During the Middle Ages Pisa was involved in various battles and played an important role in the wars and feuds. Today the city still maintains its ports and this accounts for much of its economy. Enjoy historic buildings such as the Leaning Tower of Pisa as well as the Cathedral of Santa Maria Assunta…

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Walking Tour of Pisa

Time10:30 AM

Pisa is a legendary city and one of the most famous in this region of Italy. Located on the western coast of Italy, Pisa is only 20 minutes from the Ligurian Sea and has great transport links to Florence, Livorno and La Spezia. 

During the 11th century and onwards Pisa rose to prominence and became one of the major maritime republics of Italy. During the Middle Ages Pisa was involved in various battles and played an important role in the wars and feuds. Today the city still maintains its ports and this accounts for much of its economy. Enjoy historic buildings such as the Leaning Tower of Pisa as well as the Cathedral of Santa Maria Assunta…

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Depart from Pisa to Lucca

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Walking tour of Lucca

Lucca is one of the cities most loved all of Tuscany. Located on a plain at the foot of the Apuan Alps and is less than half an hour from the coast of Versilia. Since it isn't a hilltop village, it is ideal for anyone with mobility issues as well as for anyone wishing to take a break from climbing… 

Most of the attractions in Lucca today show its ancient history: from traces of the Roman amphiteater that can be seen in the shape of the Piazza dell'Anfiteatro, to the various towers and villas from the 12th to 16th centuries. 

The walls that surrounded the old town were maintained eventually lost their military importance… but today serve as a scenic pedestrian promenade, today one of Lucca's main attractions.

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Return to our villa

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Cena! (Dinner included)

Time7:00 PM

HAPPY HOUR AND DINNER AT THE VILLA

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Overnight in Tuscan Villa

Day 9: Return to the USA

May 03
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Colazione! (Breakfast)

Time7:00 AM

BREAKFAST AT THE VILLA

Early morning private transfer to Rome's airport

For those returning home to the USA, we wish you safe travels!

We may explore flying out of Florence, but it will not be direct. There will be one international connecting flight. Options will be discussed.

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