Day Trips from Florence to San Gimignano

In the heart of Tuscany and Chianti. Hills, vineyards, unspoiled nature. Intact medieval cities. Unforgettable atmospheres.

Explore the enchanting landscapes of Tuscany on this full-day adventure from Florence. Visit iconic sites like the Leaning Tower of Pisa and the medieval gem of San Gimignano, renowned for its impressive towers and stunning views. Discover the historic charm of Siena, with opportunities to delve into its rich heritage through an optional guided tour of the Duomo and other landmarks. Finally, unwind with a delightful wine tasting at a Chianti winery, where you can savor local wines and shop for unique souvenirs. Lunch will be a typical tuscan meal with antipasto, cheese, bruschette, pasta al ragù, dessert, wine and water. Vegetarian Menu available upon request.

Leave the bustle of Florence behind and dive into the rolling hills of Chianti on a scenic bus tour from Villa Costanza. Visit two authentic family‑run wineries, enjoy up to eight delicious wine tastings paired with local Tuscan bites, and wander through a true medieval village perched in the countryside. A perfect experience for wine lovers and curious travelers alike. Set off through a landscape of vineyards, olive groves, and soft green hills. Explore the medieval charm of Monteriggioni or the iconic town of San Gimignano, famous for its towers and timeless beauty. Discover historic cellars, taste Chianti Classico, local olive oil, balsamic vinegar, and freshly made bruschette—all while immersing yourself in the authentic flavors and traditions of Tuscany.

Savor the sights and tastes of Tuscany on this private wine-tasting tour of the famed Chianti region. From Florence, journey across the Chianti hills, covered with vineyards and olive groves, toward Greve where you will make a first stop before heading for a respected Chianti winery to visit the cellars and learn about the production methods of the Chianti Classico. After a Tuscan-style lunch paired with wine, you'll head towards a second Chianti winery for another wine tasting.

Discover a piece of ancient Tuscany with this hassle-free private round-trip transfer from Florence to San Gimignano. Set off from your Florence hotel for the idyllic small town that transports you back to the Middle Ages with its perfectly preserved center. Enjoy a few hours of free time to explore the city walls and five impressive entrance gates plus well-preserved old town. Then simply sit back, relax, and enjoy the return ride to your Florence hotel.

Siena and San Gimignano are two of the most beautiful cities in Tuscany, but to visit both in a single day from Florence, private transportation is required. Let someone else do the driving—and the planning—during this full-day private excursion. Stop wherever and as often as you like on a fully customized tour, and enjoy the full attention of a knowledgeable driver throughout the day.

Visit two of the most captivating villages in the Tuscan countryside on this private day tour from Florence. Travel in a Mercedes minivan to the Etruscan town of Volterra, known for its 3,500 years of history, ancient city walls and museums. Stop at a local farm or restaurant for an optional lunch before visiting the UNESCO-listed medieval village of San Gimignano. Enjoy the personalized attention of a private guide and a customized itinerary to match your interests. Price is per group, based on a maximum of eight passengers per vehicle.

This full day tour will take you into the hills of Tuscany passing along one of the country’s most beautiful and famous routes.First stop is a surprise for most:a quick visit to the WW2 American war Memorial where more than 4400 brave US soldiers rest in peace.Next stop is Siena, home of the famous Palio.Your driver will take you through the tight streets of this fierce rival of Florence until the 16th century. You will be told all about the contradas, the buroughs in which Siena is divided. Next you will stop by the marvelous Duomo of Siena.You will be given all the info about its tormented building history so that you can enjoy some time on your own. After lunch, we will move on to San Gimignano.The medieval village’s towers symbolized the prosperity of the village and the wealth of its merchants.It is therefore known as the”Manhattan of the Renaissance”.You will have time to stroll the tiny alleys and perhaps, taste their “Vernaccia” white wine, before heading back to Florence.

Explore Tuscany’s art, culture, and medieval history on this 8-hour private tour from Florence. Visit the enchanting towns of Volterra and San Gimignano at your own pace while traveling through the picturesque Chianti countryside with a knowledgeable private driver.

Spend a full day exploring a trio of Tuscany’s best-preserved medieval cities on a private day trip from Florence. Skip the stress of renting a car and let a personal chauffeur take your group directly from your hotel door through the Tuscan countryside and into the historic centers of Siena, San Gimignano, and Pisa. Explore the cities at your own pace, with the help of tips and local guidance from your driver.

Spend a full day touring the Italian cities of Siena, San Gimignano, and the surrounding area of Chianti. Specifically designed for guests staying in Florence, get picked up directly from the hotel in a comfortable vehicle and take a private tour of these Tuscan hotspots. Learn about the area’s Gothic and medieval history, and enjoy the local vineyards.

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.

Cover several Tuscan towns without the need to rent a car on this group tour from Florence. Stop in the medieval hilltop town of San Gimignano before seeing the intact walls of Monteriggioni. Then enjoy a typical Tuscan lunch at a Chianti winery that includes a guided wine tasting and “vin santo." Top off your trip in Siena to explore its historic city center with a stop at the Duomo.

Explore the Chianti countryside on this full-day private tour of Siena and San Gimignano. Departing from Florence, head first to Siena for a walking tour of the city’s medieval streets. Admire the palaces and Piazza del Campo, followed by time to explore independently. Then travel via the fortified village of Monteriggioni to the town of San Gimignano and discover the medieval architecture and art on your own before heading back to Florence.

Traverse Tuscany in search of architecture, landscapes, and local flavors—without needing to self-drive—on a small-group tour departing from Florence. See the iconic Leaning Tower of Pisa, admire the Siena Duomo, and stroll through the medieval streets of San Gimignano and Monteriggioni. Plus, relax with lunch and a Chianti wine tasting to complete your Tuscan adventure.

Explore some of the most popular Tuscan hill towns on this day trip to Siena, San Gimignano, and Monteriggioni from Florence. Enjoy visiting each town independently while also having the round-trip transportation organized in advance. Learn about the famous region from the tour leader on board the bus, listening to informative commentary as you travel.

Skip the hassle of renting a car ad explore the Tuscan countryside on a full-day tour to Pisa, Chianti, and San Gimignano from Florence. See the iconic Leaning Tower and its cathedral. Continue to the UNESCO-listed medieval town of San Gimignano for a tour and a typical Tuscan lunch with wine tasting. Conclude with a visit to Siena and its cathedral (if the option is selected).

Experience the heart of Tuscany with ease on a guided tour from Florence to Siena, San Gimignano, and a charming Chianti winery for lunch. Enjoy the convenience of round-trip transportation as a knowledgeable tour leader showcases the region’s must-see sights. Begin in Siena, where you’ll explore the historical Piazza del Campo. Next, indulge in a delightful 3-course lunch and 6 local wines at a traditional winery, savoring the authentic flavors of Tuscany and stroll its vineyards. Finally, take in the stunning views of San Gimignano, renowned for its striking medieval towers and nickname, the "Medieval Manhattan."

Sample locals wines at two family-owned vineyards in Tuscany on a gourmet tour from Florence that includes a 3-course lunch of regional dishes. Visiting two different vineyards gives you an expansive introduction to local wines—and with a professional to handle the twists and turns of Tuscany’s narrow roads, you can enjoy all the wine you want without worrying about driving.

Experience two of Tuscany’s most iconic hill towns—Siena and San Gimignano—on this private day tour, complete with a visit to a carefully selected winery for wine tasting and a traditional Tuscan lunch. Travel in comfort aboard a private Mercedes A/C minivan or similar vehicle, accompanied by an expert English-speaking driver-guide with in-depth knowledge of the region’s history and art.

Let us guide you through the medieval and legendary towers of San Gimignano. In the heart of Chianti, treat yourself to a break among centuries-old vineyards with a traditional Tuscan lunch and a tasting of fine wines. An exclusive tour, in a private car with all the comforts, for those seeking authentic emotions, unique flavors, and endless beauty. An experience steeped in history, nature, and fine wine. Book your trip to the heart of Tuscany now!

Explore the enchanting medieval towns of San Gimignano and Certaldo on this full-day Tuscany tour. Begin with an early visit to San Gimignano, allowing you to wander its stunning streets and iconic towers before the crowds arrive. Then, head to Certaldo, known for its authentic charm and rich history as the birthplace of Giovanni Boccaccio. Enjoy a leisurely lunch at an organic winery, savoring delicious local dishes paired with exquisite wines while soaking in views of the picturesque Tuscan landscape. - Tour duration: 7 hours with a semi-private setting for up to 8 guests - Luxury transportation from/to Florence included - Visit two unique towns: San Gimignano and lesser-known Certaldo - Indulge in a farm-to-table lunch at an organic winery overlooking the hills - Guide for the day always with you

On this wine-tasting tour, you will sample some of the region’s best Tuscan wines. Every glass is perfectly paired with local cured meats, cheeses, and a homemade pasta dish, or a full course meal, depending which wine tasting experience you choose (please inform us if you have any dietary restrictions).

Check out two villages that not all tourists visit, since they are off the beaten path in this trip to medieval Tuscany from Livorno, Pisa, or Florence. This private tour is tailored just for you and your group, so you can spend more time on what interests you, and skip what doesn’t. Explore the Roman Amphitheatre, Rossi Alabastri Volterra, and the historic center of San Gimignano without a guided walking tour included.