Spend five days exploring the art and cuisine of Italy's Tuscany region. Discover Renaissance 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 the 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 Arrive in Florence, Italy's Renaissance Capital Florence
Day 2 Free Day in Florence: Explore at Your Own Pace Florence
Day 3 Day Trip to San Gimignano, Chianti Winery Tour & Tasting Florence
Day 4 Day Trip to the Tuscan Cities of Pisa & Lucca Florence
Day 5 Depart Florence  

Detailed Itinerary

Day 1: Arrive in Florence, Italy's Renaissance Capital

Welcome to Florence
Enjoy the art of the aperitivo before a dinner of Tuscan fare in Florence

Welcome to Florence! Upon arrival at the airport, transfer to the city center and check into your hotel. Once you've had time to rest and settle, step outside and begin exploring the elegant, pedestrian-friendly streets of Tuscany's Renaissance capital at your own pace.

Florence is home to a plethora of Renaissance masterpieces and architecture, including the iconic Il Duomo, a terracotta-tiled dome that's impossible to miss, and the Galleria dell'Accademia, which displays Michelangelo's "David" sculpture. Immerse yourself in the city's cultural and artistic vibe with a visit to Studio Artemisia, located steps away from the Ponte Vecchio, to learn more about ancient fresco painting techniques. Alternatively, stroll through the peaceful Boboli Gardens and admire Isolotto, a tiny 17th-century island surrounded by sculptures and greenery.

In the evening, make your way to the historic L-shaped Piazza della Signoria, located in front of the Palazzo Vecchio, for aperitivo (an aperitif, usually spritz or wine, accompanied by small bites) and experience the Italian art of dolce far niente (the sweetness of doing nothing). As the sun sets, head over to the bustling Sant'Ambrogio neighborhood for traditional Tuscan fare.

Day 2: Free Day in Florence: Explore at Your Own Pace

Duomo & Gelato
Be sure to visit one of the city's famous gelaterie

Today is yours to explore the city at your leisure. Head over to the Mercado di San Lorenzo, where you can grab a midmorning pastry and espresso and spend an hour or two soaking up the atmosphere and browsing the stalls. You'll find plenty to catch your eye with the various artisanal leather goods the city is famed for, alongside pottery, beautiful notebooks, jewelry, and much more. When you're feeling peckish, head inside to the Mercado Centrale, where you'll find all the foodie stalls and plenty of options for a great lunch. 

In the afternoon, wander over to Piazza della Republica and pause for refreshments at one of the historic cafés that line the square. Continue on to Il Ponte Vecchio, a medieval stone bridge with an array of jewelry shops and beautiful views along the River Arno. As the afternoon fades, end your day with a visit to Piazzale Michelangelo. It's an uphill walk (or you can catch a cab or bus), but you'll be rewarded with splendid sunset views across the whole of Florence and the rolling Tuscan countryside.

Plan your trip to Italy
Chat with a local specialist who can help organize your trip.

Day 3: Day Trip to San Gimignano, Chianti Winery Tour & Tasting

Explore Plaza della Cisterna in San Gimignano
Explore Plaza della Cisterna in San Gimignano—one of Tuscany's most picture-perfect hill towns

This morning, you'll embark on a tour of the local towns dotted along the rolling hills outside Florence. Admire the landscape filled with olive groves, cypress trees, and farms as you approach one of the region's gems—the medieval village of San Gimignano. This UNESCO World Heritage Site is known for its 14th-century Torre Grossa, which, at 177 feet (54 m), stands as the tallest of the town's 14 towers. Explore the beautiful squares and stop for award-winning gelato in Piazza della Cisterna or a glass of the local Vernaccia di San Gimignano white wine.

Your next stop is a winery in the Chianti Hills, where you'll tour the vineyards and cellars behind the region's eponymous wine. Made from a minimum of 80% sangiovese grapes, Chianti Classico is produced from vineyards within a distinct area that stretches between the cities of Florence and Siena. Learn about the centuries-old production process and then sit down to a tasting of various vintages accompanied by a typical Tuscan lunch of cured meats, cheeses, a primo (usually a pasta course), and a choice of dolce (dessert). 

After lunch, you'll visit nearby Siena and tour the Duomo di Siena, a magnificent Romanesque-Gothic cathedral known for its intricate marble inlay floor and treasures, including works by Bernini, Pisano, and Donatello. Roam the narrow cobbled backstreets until you reach the vast Piazza del Campo, the town's central square and site of the famous Palio di Siena horse race. It's a great spot for aperitivo and to catch a breather before you finish the day with a visit to the medieval fortress of Monteriggioni and head back to Florence for the evening. 

Day 4: Day Trip to the Tuscan Cities of Pisa & Lucca

End today's explorations among the art and architecture of Lucca

Finish your tour of Tuscany with visits to two of the region's most well-known cities. Start in Pisa, a 1.5-hour drive away on the coast, where you'll start your guided walking tour with a stroll around the city's medieval walls. Visit the Cattedrale di Pisa to see the Romanesque masterpieces, the 12th-century Baptistery, and the ancient cemetery. Finish in Piazza dei Miracoli and climb the 294 steps until you reach the campanile (bell tower), where you can admire the panoramic views. Afterward, reward your efforts with gelato and a tasting of typical Tuscan wines at a nearby enoteca (wine shop).

Your next stop is the wonderful town of Lucca, famous for its art, architecture, and laid-back bohemian atmosphere. The medieval city is known for its well-preserved Renaissance-era city walls, which have been converted into a promenade. Enjoy a wander around the tree-lined paths and head into the historical center to see the Piazza Anfiteatro, Torre di Guinigi, and the Cattedrale di San Martino Cathedral. Pause for refreshments in Piazza Cittadella, where you'll find a statue of the composer Giacomo Puccini, who was born in the city.

After your tour, your guide will drop you back in Florence, where the evening is yours to enjoy at leisure. Toast your Tuscany adventure with aperitivo at one of the city's elegant rooftop bars, such as Il Continentale or Hotel Lucchesi, where you can watch the sun go down and admire the city's skyline.

Day 5: Depart Florence

Bid arrivederci to the Tuscan countryside
Bid arrivederci to the Tuscan countryside

Say goodbye, or ciao, to Italy for now. Take advantage of any extra time with one last morning stroll around Florence before transferring to the airport, where you'll catch your flight home or continue your European adventure. Safe travels!

More Great Italy Itineraries

Looking for more inspiration for your trip to Italy? Check out these other Italy itineraries, explore different ways to spend five days in Tuscany, or discover the best time to visit Italy.


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