Iconic Italy: Highlights of Rome, Florence & Venice

This 9-day, 8-night itinerary takes you on an unforgettable journey through Italy’s iconic trio: Rome, Florence, and Venice. You’ll explore the must-see landmarks of these celebrated cities while also discovering a few hidden gems along the way. Like all our itineraries, this experience is fully customizable to align with your personal interests and preferences, ensuring a trip that’s uniquely yours.

Your Scenic Arrival in Venice

Venice is pure romance—a city where arched bridges span quiet canals, gondolas glide gracefully through the water, and moonlight shimmers on the rippling surface. Venice is also a living history museum, with landmarks like the Palazzo Ducale, Piazza San Marco, and the Grand Canal showcasing centuries of art, architecture, and cultural significance. Yet, Venice is not stuck in the past—it pulses with modern energy, from the glamour of the Venice Film Festival to the vibrant celebrations of Carnivale.

The city is home to an abundance of world-renowned museums and artistic treasures. The Basilica di San Marco, with its dazzling Golden Altar, stands as a symbol of Venetian splendor in the heart of Piazza San Marco. The hauntingly beautiful Bridge of Sighs offers a poignant glimpse into history, where prisoners caught their final view of the city on their way to confinement. Art enthusiasts will revel in the Gallerie dell’Accademia, featuring masterpieces from the 14th to 18th centuries, or the Peggy Guggenheim Collection, which showcases cutting-edge 20th-century art. And this is just the beginning—Venice is a treasure trove waiting to be explored.

Built on a network of islands linked by bridges, with the Grand Canal as its central artery, Venice is a city where boats replace cars. From elegant gondolas to bustling water taxis, life flows along its iconic waterways. However, this unique charm comes with challenges. Rising sea levels and increasingly frequent high tides threaten the city’s future, making its fragile beauty all the more precious. Venice is a place that is truly timeless. A destination where history, art, and romance come together in a way that exists nowhere else in the world.

Upon arrival in Venice, a private transfer will whisk you from the airport to your accommodations, ensuring a seamless start to your journey. As you settle into your luxurious Venetian hotel, take a moment to soak in the city’s unique ambiance. Spend the evening at your leisure—perhaps enjoying a stroll along the canals or indulging in a Venetian aperitivo as the city’s lights reflect on the shimmering waterways.

Experience the Culture and History of Venice

Your morning private tour begins in the iconic St. Mark’s Square, the beating heart of Venice and a hub of history and culture. After an introduction to the Piazza and a look at the stunning exterior of St. Mark’s Basilica, step inside to explore its breathtaking interior. Constructed in 1063, the Basilica is a masterpiece of Byzantine architecture, showcasing domes, intricate marble, and mosaics. Inside, nearly every surface shimmers with gold mosaics, a testament to the city’s wealth and grandeur during its time as a dominant trading empire.

Next, delve into the history of Venetian power at the Doge’s Palace, the seat of government until Napoleon’s conquest in 1797. This grand Gothic structure houses an impressive collection of Renaissance art, including Tintoretto’s monumental Paradiso. Tour the opulent Doge’s apartments, ascend the majestic Scala dei Giganti, and explore the palace’s darker side—the prisons. These later additions, built in the 16th century, are connected to the palace by the iconic Bridge of Sighs, where prisoners caught their final view of Venice’s beauty before entering confinement. This journey through the heart of Venice reveals its opulence, artistry, and enduring legacy.

Nothing captures the essence of Venice quite like a gondola ride. For nearly a millennium, these iconic boats have glided through the city’s intricate network of canals, becoming a symbol of Venice’s timeless charm and allure.

Your gondola journey will take you off the beaten path, meandering through quieter, lesser-known canals. These hidden waterways offer a glimpse into Venice’s past, showcasing the city as it was before the arrival of bustling crowds and modern traffic. Departing from the San Tomà water bus stop on the Grand Canal, your gondolier will guide you toward the peaceful San Polo district, one of Venice’s more tranquil neighborhoods. Here, savor a glass of Prosecco and sample cicchetti—Venetian bite-sized snacks traditionally enjoyed with aperitivo—while soaking in the serene atmosphere.

The ride concludes with a return to the Grand Canal, where you’ll pass some of Venice’s most magnificent palazzi and take in views of the iconic Rialto Bridge. Your journey ends where it began, near the historic Frari Church, leaving you with a newfound appreciation for the quiet elegance and vibrant history of Venice.

Venice to Florence

Begin your morning with a private water taxi ride through Venice’s iconic canals, offering a final glimpse of the city’s shimmering waterways and historic beauty as you make your way to the rail station. Board a comfortable high-speed train to Florence, gliding through the picturesque Italian countryside with its rolling hills, charming villages, and vineyards. Upon arrival in Florence, a private transfer will whisk you to your hotel in the heart of this Renaissance city.

Florence is a city where art and history greet you at every corner, captivating millions of visitors annually with its timeless beauty. From the grand Palazzo Vecchio to the iconic Uffizi Gallery, home to some of the world’s most renowned masterpieces, the city is a treasure trove of cultural wonders. The magnificent Cathedral of Santa Maria del Fiore, crowned by Brunelleschi’s awe-inspiring dome and Giotto’s elegant bell tower, dominates the skyline, while the Ponte Vecchio, lined with its historic jewelry shops, beckons travelers with its charm. On the opposite bank of the Arno, the sprawling Boboli Gardens provide a serene escape amid stunning sculptures and lush greenery.

Florence is equally renowned for its culinary heritage. As the heart of Tuscany, it offers a gastronomic experience rooted in tradition. The world-famous Chianti wines pair perfectly with the city’s signature dish, the hearty and flavorful Fiorentina steak. Whether exploring its artistic landmarks or indulging in its food and wine, Florence offers an experience that is as rich and vibrant as its history.

This remarkable collection was once the private treasure of the powerful Medici family, who amassed some of the finest works of art during their reign. When the Medici dynasty ended in the 1700s, their collection was opened to the public, transforming it into one of the most celebrated museums in the world. Today, it houses an unparalleled array of Italian Renaissance masterpieces, showcasing the evolution of art from its early beginnings to its golden age.

Begin your journey with works by pre-Renaissance visionaries like Giotto, and follow the progression of artistic genius through the groundbreaking innovations of Masaccio, da Vinci, Michelangelo, and countless other luminaries. This three-hour tour offers an intimate look at the creativity, passion, and innovation that defined the Renaissance, providing a window into one of the most transformative periods in history.

Highlights of Florence

Private Walking Tour in the morning. Afternoon at leisure. Overnight in Florence.

As the birthplace of the Renaissance, ​Florence​ combines unequaled beauty with centuries of history in a heady mix. This half-day private tour of Florence’s historic center is the perfect introduction to the city. It’s also the best way to get a complete picture of what makes Florence so beloved. After a walking tour of the city center, you’ll conclude with a visit to the Accademia Gallery. The home of Michelangelo’s marble statue of David since 1873.

Optional Activity: Palazzo Pitti & Boboli Gardens

A Day Trip Through Tuscany + Pisa

After breakfast, meet your private driver at your hotel to embark on a full-day journey to the charming towns of Lucca and Pisa. Your adventure begins at Villa Maionchi in Lucca, where you’ll enjoy a guided olive oil tasting and a tour of the estate’s historic oil cellar. Learn about the art and tradition of olive oil production as you explore the picturesque olive groves. A delightful lunch awaits, featuring a classic Tuscan menu paired with the villa’s own olive oil and wine, offering a true taste of the region.

In the afternoon, continue to Pisa for a private guided tour of the iconic Piazza dei Miracoli. Explore the Cathedral, the Monumental Cemetery, and marvel at the world-famous Leaning Tower. While entrance to the tower isn’t included, the stunning views of this architectural wonder and the surrounding square make for an unforgettable experience. This day promises a perfect blend of Tuscany’s rich flavors and historical treasures.

Tuscany to The Eternal City

Morning Transfer to rail station. Train to Rome. Transfer to hotel Overnight in Rome.

Nicknamed “The Eternal City,” Rome is a living tapestry of history, where every layer tells a story. Ancient temple ruins serve as the foundations for Christian churches, while medieval fortresses rise from the remnants of Roman theaters. Even the city’s thousand-year-old Corinthian columns now support modern walls. From its awe-inspiring art and architecture to its vibrant street life and famously chaotic traffic, Rome surrounds visitors with an energy that ensures an unforgettable experience.

Rome wasn’t built in a day, and exploring it fully takes far longer. The historic center alone offers enough to captivate travelers for a week. Highlights include Michelangelo’s masterful Campidoglio, the awe-inspiring Pantheon, the historic Palatine Hill, and the sprawling Roman Forum. Just beyond, marvel at the iconic Colosseum and the grand Baths of Caracalla. The city’s basilicas, scattered across Rome, invite deeper exploration and are well worth the time to uncover their splendor.

This half-day walking tour of Rome’s historic center begins at the iconic Piazza di Spagna. From there, stroll to the legendary Trevi Fountain, where tradition calls for tossing a coin to ensure your return to the Eternal City.

Next, visit Piazza Colonna to marvel at the towering Column of Marcus Aurelius, an ancient masterpiece erected between 176-192 AD to celebrate the emperor’s military victories. Continue to the awe-inspiring Pantheon, one of the best-preserved Roman structures in existence. Built in the 2nd century, this architectural marvel stands as a testament to the ingenuity and durability of Roman engineering.

The tour concludes at Piazza Navona, one of Rome’s most vibrant squares. Here, you’ll admire Bernini’s magnificent Fountain of the Four Rivers, a baroque masterpiece surrounded by the lively atmosphere of cafes and street performers, making it the perfect ending to your journey through Rome’s timeless treasures.

Explore the Wonders of Ancient Rome

This half-day tour begins with a visit to the iconic Colosseum, a marvel of ancient engineering constructed in 72 AD. Capable of seating up to 50,000 spectators, this grand amphitheater hosted thrilling and often brutal spectacles, captivating audiences of all social classes. Even today, the Colosseum remains a symbol of Rome’s history, culture, and enduring legacy.

After exploring the Colosseum’s interior with your guide, continue to Palatine Hill, one of the city’s oldest and most storied areas. Known as the legendary birthplace of Rome, this hill offers a fascinating glimpse into the city’s earliest days. The tour concludes at the Roman Forum, once the heart of political, social, and commercial life in ancient Rome. Here, you’ll walk among the ruins of temples, basilicas, and public spaces that were central to the daily life of the Roman Empire.

Exploring the Treasures of the Vatican

Begin your day at the Vatican Museums, home to one of the largest and most impressive art collections in the world. With the help of your expert private guide, you’ll navigate this vast treasure trove with ease. Highlights include the magnificent Raphael Rooms, the intricate Gallery of Maps, the Tapestries and Candelabra galleries, Giuseppe Momo’s stunning Spiral Staircase, and the Pio Clementino courtyard, where marble statues tell stories of ancient Rome.

No visit to the Vatican would be complete without experiencing the awe-inspiring Sistine Chapel, adorned with Michelangelo’s breathtaking frescoes. After marveling at this masterpiece, continue to Saint Peter’s Basilica, the spiritual heart of the Catholic Church and a marvel of artistic and architectural achievement. This iconic site is a must-see for anyone visiting Vatican City, offering a blend of history, faith, and unparalleled beauty.

Arrivederci, Roma

On your final day in Rome, enjoy a leisurely breakfast as you take in the last moments of this incredible city. Your private chauffeur will arrive at your hotel to ensure a seamless transfer to the airport, allowing you to relax and reflect on the unforgettable experiences of your journey. As you drive through the Eternal City one last time, take in the iconic sights and bustling streets that make Rome so unique. At the airport, your driver will assist with your luggage and ensure you are set for your scheduled departure. Safe travels, and we look forward to welcoming you back to Italy in the future!

Start Personalizing Your Experience with Windows on Travel

The journeys featured on our website can be booked as they are or can be tailored to reflect your personal travel preferences. Each experience is designed with care and expertise offering you the opportunity to discover Italy through fascinating local perspectives.

Our itineraries blend unparalleled access and deep immersion in each destination, delivered with the assurance of quality built on extensive expertise and trusted connections. To start the booking process, please request a quote below.

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Let's Connect!

We specialize in crafting highly personalized luxury travel experiences tailored to your unique preferences and desires, ensuring a vacation that's not only luxurious but also deeply personal and unforgettable. Ignite your passions and cultivate your interests with Windows on Travel.

Hi, I'm Alexis

06.

05.

04.

03.

02.

01.