This incredible Italy itinerary packs a lot into five days but doesn't skimp on the luxurious details. Explore Venice to see wide city canals and ornate palaces and feast on fresh seafood, then head to Florence for a private tour of the Accademia Gallery with an art historian and a romantic sunset cruise on the Arno River.


  • Explore Venice's canals and grand palaces on a private tour
  • Visit a traditional boatyard to see how gondolas are made
  • See world-famous art in the Accademia Gallery
  • Dine at a three-star Michelin restaurant in Florence and see Italy's largest wine cellar
  • Tour Florence's beautiful medieval piazzas and cathedrals with an art historian

Brief Itinerary

Day Highlights Overnight
Day 1 Arrive in Venice, Private Guided City Tour Venice
Day 2 Bacaro & Private Squero Tour in Venice Venice
Day 3 Train to Florence, Private Guided City Tour Florence
Day 4 Private Guided Accademia Gallery & Boat Tour Florence
Day 5 Depart Florence  

Detailed Itinerary

Day 1: Arrive in Venice, Private Guided City Tour

Gondola on the Grand Canal
Gondola on the Grand Canal

Welcome to Italy! Arrive at Venice Airport, then transfer to the city center. Once in the city, a water taxi will transport you to the town center and your hotel.

Venice in northern Italy is famous for both industry and tourism. Stretching across 117 small islands in the marshy Venetian Lagoon along the Adriatic Sea, the city has long been a commercial and cultural hub thanks to its strategic placement. Silk, grains, spices, and art were traded through the Middle Ages, making Venice very wealthy. The city is also famous for its many beautiful historical attractions, such as the Piazza San Marco and San Marco Basilica, the Grand Canal, and the ornate Doge's Palace. The Lido de Venezia is a popular luxury destination that attracts actors, critics, and other cinema industry celebrities.

In the afternoon and evening, head out for a private guided walking tour of the city's top sights. Start at Piazza San Marco (St. Mark's Square), the heart of the city's cultural and administrative district. The piazza is also home to the Palazzo Ducale (Doge's Palace), a Venetian Gothic palace built as the primary residence for the Doge of Venice in 1340.

Adjacent to the palace is the San Marco's Basilica, originally the Doge's personal chapel. The building is one of the best surviving examples of Italo-Byzantine architecture and features an impressive collection of Byzantine art, gold mosaics, and marble floors.

The palace is also connected to the next-door prison by the infamous Bridge of Sighs, which has joined the two buildings since the 16th century. The bridge features a small window onto Venice's harbor and earned its grisly name from the prisoners' sighing as they got one last glimpse of the city on their way to execution. While most visitors gather outside the bridge to look in, you'll get the best sense of history from inside the bridge, looking out from the same window as the doomed medieval prisoners.

Day 2: Bacaro & Private Squero Tour in Venice

Open-air restaurant on a canal
Open-air restaurant on a canal

Enjoy a free morning in the city. Pick from the following suggestions, then head out to explore before lunchtime:

  • Discover art at the Ca' Pesaro Galleria Internazionale d'Arte Moderna, Peggy Guggenheim Collection Modern Art Museum, and La Biennale di Venezia Art Museum
  • Explore San Giorgio Maggiore, one of Venice's smaller islands that stands separate from the main canals  
  • See an opera show at the Teatro La Fenice 
  • Haggle for produce at the busy Mestre market, held every Wednesday and Friday
  • Go shopping for luxury items on Le Mercerie and Salizada San Moisè 
  • Browse textiles, craft shops, boutiques, and galleries in the bohemian San Samuele district 
  • Rent a kayak and explore Venice from the water 

For lunch, head to a traditional bacaro, a Venetian wine bar, to try the Cicchetti—little bite-sized snacks accompanied by a glass of wine. The seafood in Venice is always fresh-caught, so try the fried squid skewer or the creamy salted codfish canapès. The mozzarella in Carrozza (a fried cheese sandwich), various cold cuts, and other delicacies are also delicious. 

In the afternoon, take a private guided tour of a traditional squero, a small boatyard where tradesmen build and repair gondolas. This squero was founded in 1884 by an expert local craftsman who changed the traditional shape of the gondola boat. These changes were permanently adopted into gondola construction and handed down over the generations to keep the art alive. 

You'll learn about the art and science of traditional gondola construction and see how beautiful boats are constructed using a combination of carefully selected natural wood for ultimate longevity. Afterward, enjoy an evening stroll in the city center, then find the perfect restaurant by the canal for a delicious meal.

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Day 3: Train to Florence, Private Guided City Tour

Ponte Vecchio bridge
Ponte Vecchio bridge

After breakfast, head to the train station to catch a train to Florence. Florence is Tuscany's regional capital and its most populous city. Long considered a cultural capital and the "Jewel of the Renaissance, Florence is home to many masterpieces of Renaissance art and architecture, including the iconic Duomo, a terracotta-tiled dome, and the Galleria dell'Accademia, which displays Michelangelo's "David" sculpture.

Spend the day exploring the top sites with an art historian on a private guided walking tour. Start in the medieval city center in the Piazza della Repubblica, one of the city's main squares. It has marked the city center since Roman times. See the Colonna della Dovizia, also known as the Column of Abundance, that marks the point where the cardus (north-south oriented road) and decumanus maximi (east-west oriented road) met and also where the Roman forum stood.

Continue to the Piazza della Signoria, the city's political center since the Middle Ages, where ceremonial events, rallies, and festivals are celebrated. Here you'll find several iconic Florentine landmarks—Palazzo Vecchio and the Uffizi Gallery, which houses works by Michelangelo and Leonardo da Vinci. The square's centerpiece is the Neptune Fountain, a popular meeting place. 

See the Ponte Vecchio bridge, a symbol of Florence's power for over seven centuries. The bridge houses buildings and shops, which have been occupied by merchants and shopkeepers since the Middle Ages. Arrive at the Italian Gothic Cathedral of Florence and climb the 400+ steps to reach Giotto's bell tower. Enjoy a private and exclusive visit to the Cathedral Terraces, which perch high above the city traffic and are generally closed to the public. From here, you'll have a birds-eye view of the whole city.

For dinner, head to Enoteca Pinchiorri, Florence's 3-star Michelin restaurant, then stroll through the city on your way back to the hotel.

Day 4: Private Guided Accademia Gallery & Boat Tour

Ponte Vecchio at sunset
Ponte Vecchio at sunset

In the morning, meet your art historian guide and visit the Accademia Gallery for a private guided tour. The Galleria dates back to 1784 when the Grand Duke of Tuscany, Pietro Leopoldo, reorganized the Academy of Arts of Design in Florence into the modern Academy of Fine Arts. The Galleria was specifically designed to house valuable works of art, and its spectacular architecture is impressive in its own right.

Among other masterpieces, the Galleria is home to one of the Renaissance's most iconic masterpieces, Michelangelo's David. This incredibly 14-foot tall Renaissance sculpture, which depicts the Biblical hero, was created between 1501 and 1504 and became a symbol of the Florentine republic's strength during a time of massive political change. Much like David facing the mighty Goliath, the Republic was threatened at the time by stronger states, not to mention the Medici family regaining power.

Enjoy lunch on your own time and spend some time shopping for souvenirs or simply enjoying the city's ambience.

Later in the afternoon, board a traditional boat piloted by a renaiolo (a traditional boatman) for a sunset ride on the Arno River. The 45-minute trip on a traditional boat will take you down the Arno from Piazza Mentana, pass under the Ponte Vecchio and Ponte Santa Trinità, and navigate by the Uffizi Gallery, the Vasari Corridor, Palazzo Corsini, and the 10th-century San Jacopo sopr'Arno Church. 

Day 5: Depart Florence

Little details of life in Rome
Little details of life in Rome

Time to say goodbye to the country of love! After one last cappuccino over breakfast, head to the airport for your connecting flight home. Safe travels!

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Map of Luxury Italian Highlights: Venice & Florence - 5 Days
Map of Luxury Italian Highlights: Venice & Florence - 5 Days