The Three Cities of Art: Rome, Florence & Venice in a Boutique Small Group Tour

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The Three Cities of Art

cities: venice - florence - rome
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Discover Rome, Florence, and Venice in Boutique Style

If you're visiting Italy for the first time, there's no better way to begin than with a small group journey through Venice, Florence, and Rome—Italy’s most iconic cities of art, history, and culture. Traveling with just 6–12 guests, you’ll enjoy the perfect blend of exclusivity and camaraderie, with expert local guides and thoughtfully curated experiences throughout.

Venice, rising like Atlantis from the sea, feels almost otherworldly—its winding canals, arched bridges, and Byzantine-inspired architecture reveal a city shaped by centuries of maritime trade and Eastern influence.

In contrast, Florence is the birthplace of the Renaissance, exuding intimacy and artistic brilliance. With its human-scale piazzas, domed cathedrals, and romantic streetscapes, it’s a city where every corner feels like a masterpiece.

Then there’s Rome, a city of grandeur and bold expression, where monumental ruins, baroque piazzas, and imperial landmarks create an awe-inspiring sense of timelessness.

Together, these three cities capture the heart, soul, and imagination of Italy. With the Your Own Italy Advantage, your small group experience will be seamless, immersive, and unforgettable—crafted with care for travelers who want more than just a tour… they want a journey worth remembering.

Day by day

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venice

Summary venice
Day 1
Day 2
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Day 1

Arrival in Venice: Welcome Dinner

Arrive in Venice, the magical city of canals, where your journey begins in true Italian style. A private boat will escort you across the lagoon to your hotel in the heart of the city. Settle into your accommodations and take in your first glimpses of this enchanting floating world.

In the evening, gather with your fellow travelers for a warm welcome dinner at a traditional Venetian restaurant. Savor regional specialties like fresh seafood risotto, cicchetti, and local wines as you toast the start of your unforgettable Italian adventure. It’s the perfect introduction to the elegance, camaraderie, and culinary delights of Your Own Italy’s Small Group Tours.

Gondolas gliding along the Grand Canal in Venice, Italy
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Day 2

Venice: A Timeless Journey Through Canals, History & Elegance

Step into the enchanting world of Venice, where history, art, and beauty blend in a maze of canals and streets. With your private guide, explore iconic landmarks and end your adventure aboard a private gondola, gliding through scenic waterways.

Start at the magnificent Piazza San Marco, the heart of Venice for centuries. Marvel at St. Mark’s Basilica, with its dazzling Byzantine mosaics, and uncover the legendary relics transported from Alexandria. Admire the Gothic grandeur of the Doge’s Palace, once the seat of Venice’s powerful rulers.

Venture beyond the crowds into hidden piazzas and narrow alleyways, where the true magic of Venice awaits. Stop at La Fenice, the city’s renowned opera house, cross the iconic Rialto Bridge for breathtaking views of the Grand Canal, and explore the lively Rialto Market, where Venetians have traded for centuries.

No visit to Venice is complete without a private gondola ride through its picturesque canals. Glide past graceful palaces, charming bridges, and historic passageways, experiencing the city as nobles once did. Let the gentle lapping of the water and the soft creak of the gondola immerse you in Venice's timeless romance.


View of from across the water of San Giorgio Maggiore Island in Venice, Italy
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Day 3

Free Day in Venice

Stroll at Your Leisure or Discover More with a Guided Tour

Today is yours to savor as you wish in the enchanting city of Venice. Meander through its labyrinth of narrow alleys and over elegant bridges, uncovering serene canals, picturesque piazzas, and hidden artisan shops tucked away from the bustling tourist paths.

Prefer a deeper dive into the city’s rich history and culture? Ask us about our highly recommended guided tour experiences, including the awe-inspiring St. Mark’s Basilica and the historic Doge’s Palace. Or embark on a scenic day trip to the island of Murano—famous for its centuries-old glassmaking tradition—and the vibrant island of Burano, renowned for its colorful homes and exquisite hand-made lace.

Venice is yours to explore, discover, and fall in love with at your leisure.

Detail of the spires on St. Mark's Basilica in Venice, Italy
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florence

Summary florence
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Day 4

Arrival in Florence & Welcome Dinner

Arrive in Florence, the cradle of the Renaissance, where cobbled streets, domed cathedrals, and timeless beauty await. Your driver will meet you upon arrival and escort you to your centrally located hotel. After check-in, take time to unwind or enjoy a leisurely stroll through the city’s elegant streets and historic piazzas.

In the evening, come together with your fellow travelers for a delightful welcome dinner at a handpicked Florentine trattoria. Indulge in Tuscan specialties, sip local Chianti, and savor the flavors that define this rich culinary region. It’s the perfect way to begin your small group journey through Italy, with great food, great company, and a touch of magic.

The cityscape of Florence, Italy with mountains in the background
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Day 5

Introductory Tour and the Accademia Gallery

Step into the heart of the Renaissance as you explore the timeless beauty, rich history, and artistic masterpieces of Florence. With its grand piazzas, architectural marvels, and world-renowned art, every street, stone, and sculpture tells a story. Led by your expert guide, you’ll uncover the genius of Michelangelo, Brunelleschi, and Ghiberti as you journey through the city that shaped Western art and culture.

You’ll begin at Piazza della Repubblica, the historic crossroads of ancient Roman Florence, before marveling at the Piazza del Duomo, home to the Florence Cathedral and Brunelleschi’s revolutionary dome. You’ll admire the Baptistery’s legendary “Gates of Paradise,” then stroll across the iconic Ponte Vecchio, lined with goldsmith shops and artisan boutiques.

Your adventure will culminate at the Accademia Gallery, where you’ll stand face to face with Michelangelo’s David—a masterpiece that captures the power and beauty of the Renaissance like no other.

The cityscape of Florence, Italy with mountains in the background
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Day 6

Lunch and Wine Tasting at Villa Machiavelli and Visit to San Gimignano

Tuscany Day Trip: Chianti & San Gimignano

Escape the bustle of Florence and embark on a breathtaking journey through the rolling vineyards, historic villages, and world-renowned wineries of Tuscany. This unforgettable experience blends the legendary wine culture of Chianti with the medieval allure of San Gimignano, offering the perfect mix of indulgence, history, and stunning scenery.

You’ll travel through the picturesque Chianti countryside, where vine-covered hills, olive groves, and cypress-lined roads create a timeless landscape. Your private driver will take you to the renowned Machiavelli Winery, where you can tour the historic cellars, savor exceptional wines, and enjoy a Tuscan lunch in a charming villa once owned by Niccolò Machiavelli himself.

Next, you’ll continue to San Gimignano, the UNESCO-listed “City of Beautiful Towers,” where soaring medieval towers rise above the Tuscan hills. You’ll wander through Piazza della Cisterna, admire stunning frescoes in the Romanesque cathedral, and explore the quaint artisan shops offering hand-painted ceramics, saffron, and local delicacies.


the Tuscan countryside in Italy
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rome

Summary rome
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Day 7

Welcome to Rome! Introductory Dolce Vita Tour

Step into the enchantment of Rome and see the city through the eyes of a true Roman. This immersive Dolce Vita Tour takes you beyond the usual sightseeing, leading you through timeless streets, iconic fountains, and awe-inspiring monuments. With your expert guide, uncover Bernini’s artistic genius, marvel at the Pantheon’s architectural brilliance, and embrace the traditions that define Roman life.

Stroll through charming piazzas, soak in the vibrant rhythm of daily life, and master the art of la passeggiata, Rome’s beloved evening stroll. Toss a coin into the Trevi Fountain to ensure your return, and uncover the hidden meanings behind Bernini’s sculptures and Rome’s legendary fountains.

This isn’t just a tour—it’s an invitation to live la dolce vita, navigate the city like a local, and experience Rome in the most authentic and unforgettable way.



Trevi Fountain at night in Rome, Italy
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Day 8

Free Day in Rome

Wander at Your Own Pace or Enhance Your Experience with a Guided Tour

Today is yours to enjoy the Eternal City however you wish. Lose yourself in the charm of Rome’s cobblestone streets, relax with a cappuccino in a sun-drenched piazza, or explore hidden gems tucked between ancient ruins and Renaissance fountains.

Want to make the most of your time? Ask us about our popular guided tour options, including skip-the-line access to the Vatican Museums, a deep dive into history at the Colosseum and Roman Forum, or a food and wine tour through the vibrant Trastevere neighborhood. However you choose to spend the day, Rome is yours to discover.

the Temple of Hercules Victor in Rome just before sunset
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Day 9

Last Day in Italy: Leisure & Farewell

Enjoy your final day in Italy with the freedom to explore at your own pace. Revisit a favorite museum, stroll through a hidden neighborhood, pick up a few last-minute gifts, or simply relax with a cappuccino in one of the city’s charming piazzas as street musicians play in the background. Let the timeless beauty of the Eternal City leave one last, lasting impression.

In the evening, gather with your fellow travelers for a memorable farewell dinner at one of our favorite Roman restaurants. Nestled in the historic center, this hand-selected trattoria offers an intimate atmosphere, exceptional local wines, and a seasonal menu that celebrates the best of Roman cuisine. As you dine on handmade pasta, fresh ingredients, and decadent desserts, raise a glass to a journey well traveled—and to the unforgettable moments that made it your own.

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Day 10

Departure – Arrivederci!

As you bid farewell to Italy, you carry with you not just memories of breathtaking landscapes, exquisite cuisine, and timeless history, but also the warmth of newfound friendships. Your driver will ensure a smooth journey to the airport, giving you plenty of time to make your flight. Though your adventure may be coming to an end, Italy salutes you with a heartfelt “Arrivederci!”—until we meet again.

Now that you’ve traveled with Your Own Italy, you’ll always have friends eager to welcome you back whenever you long for the beauty, flavors, and magic of this incredible land once more.

What’s Included

Charming Accommodations

Stay in selected 4-star boutique hotels located in the heart of Italy’s most iconic cities:

Venice – 3 nights in a charming canal-side retreat.
Florence – 3 nights in a boutique hotel.
Rome – 3 nights in a boutique hotel.

Expert Guides and Skip-the-Line Access

Enjoy the expertise of English-speaking local guides who bring Italy’s history, art, and culture to life. With skip-the-line tickets, you’ll spend less time waiting and more time exploring.

Immersive Private Tours and Exclusive Excursions

Venice:

    • Transfer to hotel
    • Welcome dinner
    • Introductory Tour and Gondola Ride

Florence:

    • Transfer From Venice Hotel to Florence Hotel
    • Welcome dinner
    • Introductory Tour and the Accademia Gallery
    • Lunch and Wine Tasting at Villa Machiavelli and Visit to San Gimignano

Rome:

    • Transfer from Florence Hotel to Rome Hotel
    • Introductory Dolce Vita Tour
    • Farewell Dinner
    • Transfer from Hotel to Airport
venice
3 nights
florence
3 nights
rome
3 nights
Package Pricing
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Pricing (per person)
Rates depend on hotel selection
Classic $4,000 per person
Deluxe $5,000 per person
The Classic Package includes handpicked 4-star hotels in central locations. The Deluxe Package offers upgraded rooms in premium 4-star or 5-star hotels for added luxury and comfort.
2025 Tour Dates
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June 1 – 10, 2025
July 6 – 15, 2025
August 31 – Sept. 9, 2025
October 5 – 14, 2025


Vacation Airfare
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To book your international flights at preferred rates, contact an UP AND AWAY TRAVEL International Specialist:
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+1 (800) 275 8001
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kyle@upandaway.com
Vacation Insurance
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We highly recommend purchasing travel insurance at the time of booking to protect against potential fund forfeiture due to cancellation or unexpected incidents such as injury or loss. We offer travel insurance through our partner, Allianz.
Awards
Tripadvisor Award
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Schedule 30 minutes call with Carmen
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Best trip ever!
We would like to sincerely thank Carmen and her team for the wonderful two week itinerary planned for us in Italy as well as your dedication and constant communication in keeping us always informed with our tour guides and drivers.
Being that this was our first time traveling to Italy, Your Own Italy made our hotel (beautiful hotels) , transportation, and tour reservations for us which made our trip stress free where we could relax and enjoy our time. All the private drivers and AP Tour Guides were wonderful, gracious, very knowledgeable and informative. We really enjoyed them and learned a lot from them.
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