Day Trips from Florence to San Gimignano

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.

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 pairing. 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.

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 Colle Alta in Colle di Val d'Elsa. This tour includes wine-tasting and a nice mix of guided exploration and free time at each destination.

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 Tuscan lunch and wine tasting (optional). 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 admission to climb the tower.

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 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.

See the Tuscan gems of San Gimignano, Siena, and Monteriggioni on a day trip from Florence. Stop first in the medieval hilltop town of San Gimignano before seeing the intact walls of Monteriggioni. 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.

Visit three of Tuscany’s top destinations on this day trip from Florence that introduces you to the history and culture of this favorite Italian region. You’ll travel by bus to Siena, San Gimignano and Pisa, where you have free time to explore each city independently. Admire the vineyards of Chianti, the Piazza del Campo, the Learning Tower of Pisa, UNESCO World Heritage–listed attractions and more.

Experience for your private group. Come with us for an unforgettable day spent visiting Siena with a professional city guide and the Chianti area accompanied by one of our expert English speaking drivers born and raised in Tuscany. -During the 8hr tour you will explore the Gothic city of Siena with its famous shell-shaped Piazza del Campo and the gorgeous cathedral, followed step by step by a licensed TOUR GUIDE! If you love to visit the cathedral there will be to pay at the guide directly euro 5 per person or euro 7pp with priority -In the afternoon you will have the opportunity to visit some of the most famous vineyards, or unknown small family businesses, see their cellars and taste their excellent wines and food. -Then explore the wonderful medieval city of San Gimignano.

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.

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.

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 light lunch of fresh regional products like bruschetta, handmade pasta, cheese, and salami. You'll also travel through the Tuscan countryside dotted with vineyards, olive groves and villas, stopping to explore the traditional village of Greve.

This Siena and San Gimignano day trip from Florence allows you to explore the two towns in Tuscany easily without having to drive yourself or rent a car. Plus, along with round-trip transport from Florence, this day trip also provides lunch and wine tastings at a Chianti winery, as well as a guide who gives you insight into each stop. Learn about the history and must-see things in Siena and San Gimignano, while also getting free time, too.

Experience the architecture, landscape, and local flavors of Tuscany on a day trip departing from Florence. Led by an English-speaking driver, visit San Gimignano, Siena, Monteriggioni, Pisa, and Chianti’s famous wine region. Admire the Leaning Tower of Pisa, the Siena Duomo, and relax with lunch and a Chianti wine tasting on this comprehensive exploration of Tuscany. This small-group tour is limited to eight people to ensure an intimate experience.

Make the most of a day trip from Florence with this private guided tour that includes all transfers and admission fees. Tour the old town of Siena and San Gimignano with a guide and then enjoy free time to explore both independently before returning to Florence.

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.

Visit three of the most captivating towns in Tuscany in a single day with this tour that includes time-saving transportation directly from Florence. Enjoy a guided tour of Siena to take in the Piazza del Campo and Duomo, then relax over a traditional Tuscan lunch with wine at a local cellar. Spend your afternoon exploring first San Gimignano and then Pisa—including the iconic Leaning Tower—at your own pace.

Explore the highlights of Tuscany with this full-day tour of Siena, San Gimignano, Chianti, and Pisa from Florence. Walk through medieval streets in Siena and San Gimignano. Have lunch and wine at a Chianti winery. See the town where Leonardo was born and admire the famous Leaning Tower of Pisa.

Explore the world-class Chianti wine region on a day trip from Florence. Stop to explore Siena's sights independently, discover the hill town of San Gimignano, famous for its medieval architecture and incredible vistas. Enjoy the delights of the town of Monteriggioni. Numbers are limited to 6/7 people per van on this tour to ensure an intimate experience.

Spend a day exploring Tuscan hill towns and history on a private tour from Florence in a luxury van. Follow winding roads through vineyards and olive groves to the medieval town of San Gimignano, a UNESCO-site with stunning views of the Tuscan countryside. Discover Italy’s Etruscan heritage in Volterra, where ancient tombs, Roman ruins and brick-lined piazzas rub shoulders with bustling alabaster workshops.

There are so many beautiful places to visit in Tuscany, but it can be tricky to travel between dispersed countryside sights without your own transport. With this tour, enjoy the luxury of having a comprehensive itinerary planned out for you and transport included. Start with a tour of Pisa's famous sights—including the Leaning Tower of Pisa, then, visit a winery in the Chianti Hills. The tour also includes a visit to San Gimignano and Siena's stunning squares and cathedral.

Discover Siena, Monteriggioni, and San Gimignano on a day trip from Florence, and indulge in a Tuscan wine tasting, too. The day-long tour starts with a guided walk around Siena’s historical center with admission to Siena Cathedral, the city’s Gothic masterpiece. In the afternoon, you’ll visit Monteriggioni for photos, stop at a Tuscan estate for lunch and wine, then amble the streets of San Gimignano at your own pace.

Experience the magic of the Tuscan countryside—and visit two UNESCO World Heritage sites—on this private, customizable day trip, direct from your door. A typical itinerary begins with a stop at Piazzale Michelangelo for Florence photos and continues through Chianti to Siena, where you'll have time to explore. After a winery visit—lunch and tastings available at your expense—explore the San Gimignano walled town and take the Strada 222 wine road home.