Given the small size of Tuscany, you can experience 3-4 destinations in five days. First-timers will enjoy Chianti wine tours, Florence's Il Duomo, and the Leaning Tower of Pisa. Art enthusiasts can learn about fresco painting at Studio Artemisia, while foodies can feast on Ligurian cuisine in the Cinque Terre and join a cooking workshop in Florence. Active travelers will traverse countryside trails and historic villages, overnight in farmhouses, and taste Tuscan fare on cycling and walking tours.

Itinerary #1: Explore Tuscany: Florence, Siena, Pisa & More

Travelers eager to experience a blend of architecture, history, and cuisine will enjoy this classic itinerary. With Florence as your base, you'll take in the sites, such as Il Duomo, and indulge in Tuscan fare in the Sant'Ambrogio neighborhood before making day trips to see the towers (and taste the wine gelato!) of San Gimignano, learn about wine production in the Chianti Hills, visit the Duomo di Siena and the fortress of Monteriggioni, and see the curious Leaning Tower of Pisa for yourself. Given that this trip includes free time, it's best for travelers who enjoy the flexibility of self-guided adventures. 

Florence's iconic skyline and the Ponte Vecchio bridge
Florence's iconic skyline and the Ponte Vecchio bridge
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  

Your journey begins in Florence, where you'll have time to take in the city's masterpieces, like Il Duomo and the famous "David" at the Galleria dell'Accademia, at your own pace. In the evening, head to Piazza della Signoria for an aperitivo (an aperitif, usually spritz or wine, accompanied by small bites), followed by traditional Tuscan fare at a restaurant in the Sant'Ambrogio neighborhood. Start your second day with a pastry and espresso at the Mercado di San Lorenzo, then continue your self-guided tour of Florence, ending with sunset at Piazzale Michelangelo with views across Florence and the Tuscan countryside. 

Take a day trip to the medieval village of San Gimignano to see some of its famous towers, including Torre Grossa, and taste the local white wine and award-winning gelato, then continue to the Chianti Hills, where you'll learn about the centuries-old wine production and indulge in a tasting. The day concludes with a tour of the nearby Duomo di Siena, a Romanesque Gothic cathedral, and the fortress of Monteriggioni. Make the most of your final full day with a visit to Pisa, known for its medieval walls and iconic Leaning Tower, and Lucca, renowned for its art, architecture, and bohemian atmosphere. Learn more

Itinerary #2: Highlights of Florence

Deep dive into art history and Tuscan cuisine with this highlights tour of Florence. You'll admire the works of Michelangelo and others at the Galleria dell'Accademia and the Uffizi Gallery, learn ancient fresco painting techniques at Studio Artemisia, sample fresh local foods from the Mercado di San Lorenzo vendors, taste Chianti wine at a countryside vineyard, and learn how to prepare traditional Italian dishes in a cooking workshop with a local chef.

Get various viewpoints of Florence's iconic skyline on this itinerary
Get various viewpoints of Florence's iconic skyline on this itinerary
Day Highlights Overnight
Day 1 Arrive in Florence, Italy's Renaissance Capital Florence
Day 2 Florence Self-Guided City Tour Florence
Day 3 Day Trip to Siena & San Gimignano Florence
Day 4 Local Cooking Class in Florence Florence
Day 5 Depart Florence  

Start your Tuscan adventure with a visit to the Galleria dell'Accademia to see Michelangelo's "David" sculpture and other works of art, then learn about fresco painting techniques at Studio Artemisia. Wrap up your first day with a leisurely walk through the serene Boboli Gardens, followed by people-watching at Piazza della Signoria and dinner in the Sant'Ambrogio neighborhood. Your second day will be spent on a self-guided city tour, starting at the Cathedral of Santa Maria del Fiore for a glimpse of the famed terracotta roof and moving to the Mercado di San Lorenzo for some artisanal eats and souvenirs. 

Next, head to the Tuscan countryside on a full-day tour that takes you to the medieval village of San Gimignano and the ancient walled city of Siena and ends with a wine tasting at a vineyard in the Chianti Hills. Your final day includes more art and culinary experiences, starting with a visit to the Uffizi Gallery, which houses work by artists like Michelangelo and Leonardo da Vinci, followed by a cooking lesson and dinner with a local chef where you'll prepare four regional dishes together and toast your Tuscan trip with a glass of prosecco. Learn more

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Itinerary #3: Exploring Italian Wines in Tuscany & the Cinque Terre

Couples, honeymooners, wine lovers, and those interested in a romantic getaway to Tuscany and the Cinque Terre will enjoy this food and wine itinerary. You'll indulge in locally produced meat, cheese, wine, and more during your farmhouse stay in Colle Val D'Elsa, sip Brunello di Montalcino wines on a tour of the Val d'Orcia, explore the ruins of Volterra and the medieval architecture of San Gimignano, and cap off your trip with sassicaia wine in Bolgheri and Ligurian cuisine in the colorful seaside villages of Riomaggiore. 

Savor some of Italy's best wine tasting experiences in Chianti
Savor some of Italy's best wine-tasting experiences in Chianti
Day Highlights Overnight
Day 1 Arrive in Florence, Transfer to Colle di Val D'Elsa Colle Val D'Elsa
Day 2 Wine Tasting in Montalcino, Visit Siena  Colle Val D'Elsa
Day 3 Day Trip to Volterra & San Gimignano, Chianti Winery Visit & Tasting Colle Val D'Elsa
Day 4 Transfer to the Cinque Terre, Visit Portovenere & Riomaggiore La Spezia
Day 5 Sassicaia Tasting in Bolgheri, Transfer to Pisa, Depart  

On arrival in Florence, your driver will whisk you to the village of Colle Val d'Elsa. Here, you'll experience Italian agritourism, including a farmhouse stay and the opportunity to taste local cheese, ham, and olives paired with wine. The next day, immerse in the tranquil landscape of the Val d'Orcia, a UNESCO Heritage Site celebrated for its cypress-lined hills and world-class wines, where you'll enjoy a meal made from local produce and savor the Brunello di Montalcino wines. A visit to Siena follows with a chance to marvel at the marble floor and works by Bernini, Pisano, and Donatello at the Duomo di Siena.

Next, you'll tour Roman ruins in Volterra and admire medieval architecture in San Gimignano, pausing to sample the local white wine, Vernaccia di San Gimignano, at a restaurant overlooking the vineyards. Then, swap Tuscany's green hills for the rugged coastline and colorful structures of the Cinque Terre. Your guide will show you the UNESCO World Heritage Site of Portovenere before heading to Riomaggiore, where you'll feast on Ligurian cuisine. Arise early on your final day so you can make stops to sip Sassicaia wine in Bolgheri and see the Leaning Tower of Pisa before your flight (or train) departs. Learn more

Itinerary #4: Tuscany By Bike: San Gimignano, Siena & Murlo

Discover Tuscany and its cuisine by bike with this active itinerary. You'll bike through the rolling Chianti Hills, stop by medieval villages, including Siena, and overnight in a farmhouse. Along the way, you'll have the chance to taste locally made wines and homecooked Tuscan fare, and you'll end the journey with a challenging ride to Montalcino—and, of course, more Italian food and wine. 

Cycle through the scenic Tuscan countryside
Cycle through the scenic Tuscan countryside
Day Highlights Overnight
Day 1 Arrive in San Gimignano, Cycle in the Chianti Hills San Gimignano
Day 2 Cycle to Siena, Tuscany's Medieval Treasure Siena
Day 3 Cycle to Murlo via Buonconvento & the Crete Senesi Murlo
Day 4 Cycle to Montalcino& the Val d'Orcia Murlo
Day 5 Depart Buonconvento  

Starting in the UNESCO World Heritage Site of San Gimignano, you'll ease into your cycling adventure with a leisurely bike ride through the rolling Chianti Hills, followed by a farm-fresh dinner and a glass of the local Vernaccia di San Gimignano wine. The next day, you'll ride 26 miles (42 km) to the walled city of Siena, passing sunflower fields, medieval castles, and churches, as well as vineyards where you can stop for a wine tasting. Then, cycle through the Crete Senesi and the strade bianche (unpaved "white roads" that wind through the countryside) en route to Murlo, a medieval walled village.

Pause for refreshments at Buonconvento, a popular pit stop along the historic Via Francigena pilgrimage route, before continuing to a boutique farmhouse where you'll enjoy a relaxed afternoon by the pool (or, in the cooler months, the sauna) and homemade Tuscan fare. End on a high note with a final 28-mile (46 km) ride to the hilltop town of Montalcino, located in the UNESCO-listed Val d'Orcia region. Reward your efforts with a glass of Brunello di Montalcino wine before returning to the farmhouse for a farewell dinner. Learn more

Itinerary #5: Walk Italy's Via Francigena: San Miniato, San Gimignano & Siena

This Tuscan getaway is another excellent option for active travelers and is best suited to those who prefer scenic rambles through the countryside. You'll walk along a section of the Via Francigena pilgrimage route, starting from San Miniato, passing through medieval villages, taking a dip in the thermal baths of Gambassi Terme, and overnighting at Tuscan farmhouses. The journey culminates with sightseeing and a hearty Tuscan dinner in historic Siena.

Follow in the footsteps of history on the Francigena Way in Tuscany
Follow in the footsteps of history on the Francigena Way in Tuscany
Day Highlights Overnight
Day 1 Arrive in the Tuscan Hill Town of San Miniato San Miniato
Day 2 Walk to Castelfiorentino, Relax in a Traditional Tuscan Farmhouse Castelfiorentino
Day 3 Walk to San Gimignano via the Thermal Baths of Gambassi Terme San Gimignano
Day 4 Walk to Convento Vecchio via Monteriggioni, Transfer to Siena Siena
Day 5 Depart Siena  

You'll arrive in San Miniato via train and have a free night to rest before your journey on the Via Francigena pilgrimage route begins. After exploring San Miniato's medieval history, you'll walk to the town of Castelfiorentino, passing cypress trees and vineyards along the way. Here, you'll refuel with a homecooked meal and spend the night at a traditional Tuscan farmhouse. The following day, you'll walk to Gambassi Terme and take a dip in the nutrient-rich thermal baths before continuing to San Gimignano, where you'll enjoy the quiet charm and 13th-century architecture after the day-trippers have departed.

Then, you'll travel by car to Gracciano for the final leg of your Tuscan walk. Highlights along the route include the boroughs of Strove and Abbadia Isola and the fortified medieval hill town of Monteriggioni. When you arrive in Convento Vecchio, you'll be transferred to Siena, where you can freshen up and then head out into the historic city to feast on gnudi (gnocchi-like dumplings with spinach and ricotta) and other Tuscan dishes, toast your accomplishments with local wines, and soak up the atmosphere and people-watching in the famous Piazza del CampoLearn more

More Great 5-Day Italy Itineraries

Looking for more inspiration for your trip to Italy? Check out these other five-day Italy itineraries, with outdoor adventures, culinary trips, and best-of tours to hit the highlights.


Map of 5 Days in Tuscany - 5 Unique Itinerary Ideas
Map of 5 Days in Tuscany - 5 Unique Itinerary Ideas