Day Trips from Florence to San Gimignano

Art, history, countryside, food. Tuscany has it all. If you only have one day free, venture into Tuscany on this day trip from Florence and discover the region's highlights with a local guide. Explore the medieval city of Siena and its cathedral before heading to the hills of Chianti for a 3-course 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.

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.

Get a taste of the Tuscan countryside on this full-day tour from Florence. Take a guided walking tour of Siena, home to the famous Palio horse race, and explore the medieval hill town of San Gimignano. Midday, visit a family-owned winery for a lunch of seasonal Tuscan delicacies paired with local wines. Tour size is limited to a maximum of 25 people.

Discover the delights of Tuscany on a private day trip from Florence. With a knowledgeable private driver, travel through the renowned Chianti wine region to visit the towns of Siena and San Gimignano. See famous landmarks like Siena’s Piazza del Campo, home to the annual Palio horserace, and the medieval hilltop towers of San Gimignano.

Escape the hustle and bustle of Florence on a day trip to the Chianti wine region, with round-trip transport from a convenient Florence location. In addition to navigating for you, your guide provides insight into the winemaking process at vineyards often missed by visitors to Tuscany. The day’s itinerary includes wine tastings, an authentic Tuscan lunch, and frame-worthy photo opportunities along the way.

Explore the Tuscan countryside during a full-day tour from Florence with horseback riding. Your guide provides a gentle horse and riding gear, then leads you through the vineyards, olive groves, and rolling hills of the Chianti region. Afterward, visit the medieval town of San Gimignano, and enjoy a 3-course Tuscan lunch with wine tasting lesson. Option available to substitute a farm tour for the horseback ride if desired.

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 is time for a stop at a Chianti winery for a typical lunch which includes guided wine tasting and “vin santo." Top off your trip in Siena to explore its historic city center with a stop at the Duomo.

Tick off several of Tuscany's most renowned locations during this full-day Vespa tour. Enjoy a photo stop and farm visit at Fattoria Poggio Alloro and take a guided stroll through the picture-perfect village of San Gimignano, with free time to explore. Tours include a three-course lunch paired with a tasting of nine local wines at Tenuta Torciano.

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.

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.

Taste the true essence of the renowned Chianti wine region on a small-group tour from Florence. Visit three hand-picked wineries to tour the wine cellars and taste different varietals like Chianti Classico. Midday, treat your senses to a lunch of fresh regional products like bruschetta, cheese and salami. Finally, travel through the Tuscan countryside dotted with vineyards, olive groves and villas, stopping to explore the traditional village of Greve. Group size is limited to 25 for a more personalized experience.

Spend a day in the beautiful Tuscan countryside sipping wine and making new friends. Visit authentic wineries for tours and generous tastings of world-famous varietals like Chianti Classico and Super Tuscan. Learn about the wines’ production and flavor profiles from a sommelier guide, and round out your palate with samplings of high-quality balsamic vinegar and olive and truffle oils. Also, visit the charming medieval village of San Gimignano for free time to explore the winding streets and artisan shops.

Spend a day in Tuscany, visiting the cities of Siena, Pisa, and the medieval town of San Gimignano. With a private driver, benefit from a more flexible itinerary with plenty of free time. Enjoy a stroll through Siena’s history-rich Old Town, then admire views over the Tuscan countryside from San Gimignano. Finish with a visit to Pisa’s Piazza dei Miracoli, and snap a photo in front of the Leaning Tower of Pisa before your return to Florence. Lunch and entrance fees are at your own expense.

Ideal for travelers looking to maximize their time, this tour visits Siena, San Gimignano, and Pisa from Florence in one day of sightseeing. Travel along the Chianti road to Siena and see the town’s famous Piazza del Campo and Gothic cathedral. Then, head to San Gimignano for lunch and wine tasting (own expense) with time set aside for sightseeing and shopping. The tour finishes in Pisa, where you’ll have the chance to visit the Leaning Tower of Pisa.

To try some of Italy’s most famous white wine, visit San Gimignano on this small group, intimate tour from Florence. You’ll have transport provided the entire day, while you visit a boutique winery, medieval caves, Piazza del Campo, and more hidden gems of Sienna. Taste chianti wine, sample local cheese, bruschetta, and salami, and maybe treat yourself to the region’s famous ice cream.

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.

When visiting Florence, don’t miss a day trip to the scenic, gourmet paradise of the Tuscan countryside. On this small-group tour, visit the remarkably well-preserved medieval town of Siena, home to a magnificent cathedral and the famous Palio horse race. Indulge your taste buds with a seasonal lunch and wine tastings at a family-run farm in the Chianti region, and wander the storybook streets of the UNESCO-listed village San Gimignano. Group size is limited to 14 for a more personalized experience.

Discover the inspiring landscapes and famous flavors of the Chianti wine region on a small-group tour from Florence. Enjoy leisure time to explore the charming medieval town of San Gimignano with helpful pointers from your guide. Visit local wineries for tours, followed by a tasting of renowned Chianti varietals along with a traditional Tuscan lunch.

Discover two of the most charming and best-preserved medieval villages in Tuscany on a private day trip from Florence. Travel in a deluxe minivan through the countryside to the World Heritage-listed town of Siena, known for its majestic cathedral and pedestrian-only Piazza del Campo. After free time to explore at your leisure, continue on to the lovely hill town of San Gimignano. Get recommendations from your driver and guide on the best places to shop, dine and visit during this completely customized day.

Get out of Florence for the day to see other Tuscany highlights on a private tour to Siena, San Gimignano, and Monteriggioni. Reaching these countryside gems can be difficult without a car, but door-to-door transport and all logistics are arranged, so you can focus on taking in sights like Siena’s famous Piazza del Campo and the UNESCO-listed medieval towers in San Gimignano. Complete the experience with an optional private lunch at a hand-picked Chianti farm or winery.

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. 

Get a true taste for the Tuscan countryside with this day trip to Siena, San Gimignano and a Chianti winery for dinner. Departing from Florence, venture first to the city of Siena for a guided tour through the Piazza del Campo, the site of the renowned Palio horse races, as well as a surprise food tasting. Afterward, wander the hilltown of San Gimignano before heading to a Chianti winery for a delicious 3-course dinner, complemented by fine local wine. Your trip is reserved to 16 people to keep the experience intimate.

Florence is the capital of Tuscany, and the city makes the ideal base from which to explore this beautiful corner of Italy—but organizing travel and tickets individually is time-consuming. With this tour, begin at your Florence hotel and spin into the Tuscan countryside by private vehicle with your guide. Visit top attractions including UNESCO–listed Pisa and medieval Siena, and gaze out over vineyards and olive orchards in Chianti.

Spend a day in the Tuscan countryside with this day trip from Florence to San Gimignano and the Chianti area, including a wine tasting. Enjoy a stroll in the charming town of San Gimignano before trying wine at a local farmhouse. Then, explore Greve in Chianti and visit some local food shops.