Spend five days exploring the art and cuisine of Italy's Tuscany region. Discover Rennaissance art in Florence, browse bustling markets for fresh produce and cured meats and stroll through narrow medieval streets to see the 1,000-year-old Ponte Vecchio bridge. Head to the Tuscan countryside to visit Siena, tour a typical Chianti winery, and see the medieval Monteriggioni fortress. End your visit with a trip to see the famous leaning tower of Pisa and Lucca's historic city walls.


  • Explore famous Tuscan cities of Siena, Pisa, and Lucca
  • See Michelangelo's 'David' sculpture in the Galleria dell'Accademia
  • Sample regional wines in the famous Chianti Classico wine region
  • Tour medieval castles and explore Tuscany's culture

Brief Itinerary

Day Highlights Overnight
Day 1 Arrival in Florence Florence
Day 2 Full day in Florence Florence
Day 3 Siena and the Tuscan Countryside Florence
Day 4 Pisa and Lucca tour from Florence Florence
Day 5 Departure  

Detailed Itinerary

Day 1: Arrival in Florence

Various cured meats in the Mercato Centrale
Various cured meats in the Mercato Centrale

Welcome to Florence, the capital of Italy's Tuscany region! Arrive at Florence Airport and transfer to the city center to check in to your hotel. Spend the rest of the day relaxing and settling in, or head out for a relaxing stroll and dinner downtown.

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. Make the most of your time at some of these spots:

  • Head to Studio Artemisia, located steps away from the Ponte Vecchio for a class in ancient fresco painting techniques
  • Visit the Mercato Centrale, a 19th-century open-air market, to browse for a wide selection of vegetables, fruits, meats and cheeses, and a variety of lunch spots  
  • Take a walk through the peaceful Boboli Gardens to see the oval-shaped Isolotto, a small island surrounded by various sculptures and lots of greenery 

In the evening, stroll around the historic L-shaped Piazza della Signoria, located in front of the Palazzo Vecchio, for some people watching followed by dinner and drinks in the hip Sant'Ambrogio neighborhood.

Day 2: Full day in Florence

Ponte Vecchio bridge
Ponte Vecchio bridge

Spend the day exploring the top sites, located in the medieval city center. Popular highlights include the sprawling 15th-century Pitti Palace and the world-famous Uffizi Gallery, which houses works by artists like Michelangelo and Leonardo de Vinci. As a center for art, Florence has hosted many of European history's most notable figures, including Botticelli, Donatello, Dante, Boccaccio, and Niccolò Machiavelli. 

In the afternoon indulge yourself on the decadence of Tuscany's culinary delights. A walking tour of the city together with a guide is the perfect way to discover the region's history and find the best off-the-beaten-path gelato and coffee shops. Sample wares from city markets to find the best of the best. Try truffle panini, fresh-pressed Tuscan olive oil, handmade chocolate focaccia, finished with a glass of chilled prosecco or Chianti wine.

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Day 3: Siena and the Tuscan Countryside

Siena Cathedral and medieval Old Town in Siena
Siena Cathedral and medieval Old Town in Siena

In the morning head to the Tuscan countryside to explore the Chianti Region. Your first stop is the medieval village of San Gimignano, a UNESCO World Heritage Site located an hour away from Florence. Explore the beautiful squares, palaces, and churches of the city and before grabbing a coffee in an open-air cafe. 

Continue to the Chianti Classico wine region to visit a typical Tuscan winery. Tour the cellars and vineyards, then enjoy a wine tasting accompanied by a delicious Tuscan lunch of pasta, cured meats, cheeses, and local desserts. 

In the afternoon visit nearby Siena, located a scenic hourlong drive away, to see the magnificent Cathedral and Town Hall, site of the famous horse race of the Palio. Finish the day with a visit to the medieval fortress of Monteriggioni before returning to Florence for the night.

Day 4: Pisa and Lucca tour from Florence

Lucca from Guinigi Tower
Lucca from Guinigi Tower

Spend today diving into Tuscany's history and traditions with visits to Pisa and Lucca, two of the regions most iconic cities. 

Go for a guided walking tour of Pisa, located an hour and a half away on the coast, to see the famous leaning tower at the Piazza dei Miracoli, the cemetery and the cathedral. The tour continues with a stop to see a typical Tuscan wine shop with a tasting of regional wines. 

Continue your visit to nearby Lucca, famous for its art and Renaissance architecture. Enjoy a pleasant stroll along parts of the old city walls, then head into the historic center to see the Piazza Anfiteatro, Guinigi Tower, San Martino Cathedral. Finish your day in Florence with dinner and drinks in a family-style local restaurant.

Day 5: Departure

Train arrives to Enna railway station near Sicily
Train arrives to Enna railway station near Sicily

Time to say goodbye to Tuscany - for now! Connect to the train station or airport for your flight home. Safe travels!


Map of Explore Tuscany: Florence, Siena, Pisa & More - 5 Days
Map of Explore Tuscany: Florence, Siena, Pisa & More - 5 Days