Top Tuscany Day Trips

See all that Tuscany has to offer on this day trip to Pisa, Siena, and San Gimignano from Florence. Led by an expert guide, explore the main square and Gothic cathedral in Siena, followed by a traditional, 3-course lunch with wine. Afterward, enjoy free time to stroll the medieval streets of San Gimignano independently, as well as the city of Pisa, famous for its UNESCO-listed Leaning Tower. Your full day of sightseeing concludes with transportation back to Florence.

Art, history, countryside, food. Tuscany has it all. If you only have one day free, book this Tuscany day trip from Florence to discover the region’s highlights with a local guide. Explore the city of Siena and the cathedral, and then take to the Chianti hills for a Tuscan lunch and wine tasting. Roam the streets of San Gimignano, and travel to Pisa to admire the architectural drama of Cathedral Square — home to the UNESCO-listed Leaning Tower of Pisa. Upgrade to include skip-the-line entry, if you wish.

Explore the Italian Riviera on this day trip to the beautiful Cinque Terre from Florence, with transport between each small town provided. Led by a tour guide, discover each fishing village by coach, train, and boat, from the beaches of Monterosso to the charming streets of Riomaggiore. Stop for a swim in the turquoise waters and upgrade to include a traditional Italian lunch. Soak up all the character of this UNESCO-listed region before heading back to Florence.

Experience the UNESCO-listed Cinque Terre in one day with a guided tour through the five idyllic fishing villages of old-world Italy. Following the walking trails along the cliffs of the national park, you will see glorious views of this unspoiled stretch of the Italian Riviera. Check out the highlights and learn about the area as you complete a 3.4-mile (5.5-km) route with your guide. If you choose the tour option without hiking, the train will be used instead to move between villages.

Experience the famous beauty and flavor of Italy’s Chianti wine region on this half-day tour from Florence. Travel through the rolling hills and vineyards of the Tuscan countryside, stopping at two estate wineries to taste authentic Chianti wines and snack on regional specialties like bruschetta and cheese.

See the Tuscan gems of San Gimignano, Siena, and Chianti on a day trip from Florence. Stop first in the city the medieval hilltop town of San Gimignano. Then it's off to the village of Chianti for a tasting of local blends and delicious lunch at a winery. Top off your trip in Siena to explore its historic city center with a stop at the Duomo.

Ride a vintage Vespa through Tuscany on this tour from Florence. A local guide leads the way up through the scenic hills, where you pass the famous Piazzale Michelangelo and the Church of San Miniato al Monte. Afterward, head back to our country estate for a traditional Italian meal to top off your journey. To ensure an intimate experience, this tour is limited to 10 travelers.

Discover some of the highlights of Tuscany on this day trip from Florence by coach. Visit historical hill towns Pienza, Montalcino, and Montepulciano; admire the gorgeous, vineyard-covered scenery of Orcia Valley (Val d’Orcia); and enjoy cheese and wine tastings as you stop at local wineries and other venues. It’s a great day out in the Italian countryside.

Experience the true flavor of the Tuscan countryside on this Chianti wine tour from Florence. Led by a professional tour escort, the tour includes visits local wineries set in scenic villages. Sample the most revered Tuscan wines, learn the characteristics of each blend and hear the winemakers’ secrets. Later, stop for a look at the fortress of Castellina before your return to Florence.

Visit San Gimignano, Monteriggioni, and Montalcino on a day trip from Siena, and discover medieval architecture, wine, and stunning views of Tuscany. With ample free time in each of the hill towns, the tour also includes lunch at a Monteriggioni winery plus samples of Chianti and Brunello di Montalcino wine.

Enjoy a full-day tour into the heart of the beautiful Tuscan countryside. Visit the town of San Gimignano, the wine territory of Chianti, the medieval town of Siena, and the Monteriggioni fortress. If you choose the option with lunch, you'll have the chance to spend your lunchtime in Piazza del Campo, where every year the Palio Horse Race takes place.

Discover three of Tuscany’s most iconic destinations on a full-day tour from Florence by coach. Snap photos of the famous Leaning Tower and Piazza dei Miracoli in Pisa, stroll through the UNESCO-listed hill town of San Gimignano, and step inside Siena’s cathedral. Enjoy a traditional Tuscan lunch in Piazza del Campo.

Head to the Italian Riviera on a day trip from Florence to the Cinque Terre, a UNESCO World Heritage site made up of five cliffside villages perched dramatically on the sea. After the drive from Florence, you’ll visit the villages of Manarola, Monterosso, Vernazza and Riomaggiore, traveling by boat (weather dependent) and short train rides. The villages may also be reached by walking along the popular path that links them, taking you past terraced vineyards and providing spectacular views of the Mediterranean.

Chianti is home to Italy’s most scenic wine country and top cellars, but exploring the rural roads on your own can be frustrating. With this wine tour, set off directly from Florence and visit two different wineries in the Tuscan hills to tour the vineyards, visit the cellars, and relax over guided tastings. Sip local reds and whites plus sample balsamic vinegar and extra-virgin olive oil while enjoying views over the Chianti countryside.

Combine medieval gems, fine wines, and UNESCO-listed monuments on this full-day tour of central Tuscany from Florence. Marvel over the medieval castle of Monteriggioni; explore the architectural wonders of historic Siena; and admire the striking skyline of hilltop San Gimignano. Enjoy Siena and finish your tour with a wine tasting at a local winery in the Chianti region.

Visit two of the most popular day trip destinations from Florence in one tour on this small-group trip to the Cinque Terre and the Leaning Tower of Pisa. Enjoy a boat ride along the enchanting coastline of the Cinque Terre, then choose between a hike or train trip to another village. Stop in Pisa on the way back to Florence to see the famous leaning tower.

See Italy from behind the wheel of a retro Fiat 500 on this half-day tour through Tuscany. Take a spin around the countryside, enjoying panoramic views of Florence and a stop at the Church of San Miniato al Monte. Your guide will lead the way to a private terrace, where you’ll enjoy a delicious Tuscan lunch before cruising back to your original departure point in Florence.

Get a true taste of Italy's famous Chianti region on this full-day wine and food tour departing from Florence. Led by a guide, travel through the Tuscan hills by a 4x4 off-road vehicle, stopping to visit a wine estate and historic villa, and a cellar specializing in bottles of Chianti Classico. Sample the finest specialties at each stop, and save room for a 3-course meal in the Chianti countryside before making the return trip to Florence.

See the iconic Leaning Tower on this half-day trip to Pisa from Florence. Admire Cathedral Square and the Pisa Baptistery as you follow an expert guide past the city’s main attractions. After posing with the UNESCO-listed Leaning Tower of Pisa, some time to explore the area independently. Your trip concludes with transportation back to Florence.

Visit the highlights of Tuscany in a single day on a tour from Florence. Explore Pisa, Chianti, San Gimignano, and enjoy a guided walking tour and entrance ticket to the cathedral Siena. Then visit a family-run Chianti winery for a traditional Italian lunch accompanied by a Chianti tasting. 

Discover the charming seaside villages of the Ligurian coast on this full-day tour to Cinque Terre from Florence. Travel through the rolling hills of Tuscany to arrive at the dramatic rocky coastline, and take the train to visit the villages of Riomaggiore, Vernazza, Monterosso, and Manarola as well as Porto Venere. Enjoy free time to stroll through the winding streets, swim at picturesque beaches, and or upgrade to include lunch.

Immerse yourself in Tuscan culture, cuisine, and history on an 8-hour group shore excursion from Livorno. Comfortable and efficient transfer by coach ensures that you maximize your day on dry land and return to port with time to spare before your ship’s departure. Florence highlights include the Central Market, Ponte Vecchio, and multiple iconic piazzas. Round-out your Italian adventure with a visit to the Piazza dei Miracoli in Pisa.

Get a taste of Chianti without a long day trip or drive using an e-bike to visit a vineyard on the outskirts of Florence. Easily scale the lovely Florentine hills with a battery-assisted boost and directions on an included GPS device. Sample Chianti-style wine and other Tuscan products at a vineyard in the ancient Etruscan town of Fiesole, and enjoy inspiring views of Florence on the ride back down.

Explore the Italian gems of Pisa and Lucca on a day trip departing from Florence. Head to Pisa first, admiring the impressive square of Piazza dei Miracoli as your local guide discusses the historic buildings around you. See the Baptistery, the Duomo and the city’s most iconic attraction, the UNESCO-listed Leaning Tower of Pisa. Afterward, journey to Lucca for a walking tour of the Cathedral and Piazza dell 'Anfiteatro. Top off the day with a sweet slice of Lucca’s signature cake before traveling back to Florence.