Day Trips from Florence to San Gimignano

Swap Florence’s urban buzz for Tuscany’s rural charm on this full-day tour of San Gimignano and Siena. Wander San Gimignano’s medieval lanes and climb its ancient towers for panoramic views over the countryside. Sip local wine over lunch at hilltop winery, then head to Siena to explore the Gothic cathedral and Piazza del Campo, home to the Palio horse races. Explore solo or with a private guide—your driver handles the rest.

A wonderful day visiting the medioeval village of San Gimignano one of the main villages of Tuscany called the medioeval Manhatten because for all his towers and after 2 hours free to walk around on this village full of traditions and local small leather shops where you can find a piece of tradition of our land, you will enjoy a lunch and wines tasting of a typical local vinery all included on the price of the Tours.

Indulge in an half-day private day tour of Siena and San Gimignano from Tuscany. This tour service strives to deliver an exceptional experience and promises to live up to it by taking you on a luxurious journey in a Mercedes Benz Minivan. Your impressive team of English-speaking drivers have years of expertise and will leave no stone unturned to give you an unparalleled experience and knowledge of Italian culture.

Begin your private day trip with hotel pickup in Florence by a friendly, English-speaking driver in a comfortable, air-conditioned vehicle. Travel through Tuscany’s scenic hills to explore two iconic destinations. First, visit Siena, known for its medieval streets, Piazza del Campo, and Gothic cathedral. Then, enjoy an optional lunch and wine tasting at a local vineyard nestled among the rolling countryside. Continue to San Gimignano, a UNESCO-listed hilltop town famed for its medieval towers, charming streets, and stunning views. This fully customizable tour lets you adjust stops and timing. End the day with a relaxing ride back to Florence, filled with memories of Tuscany’s beauty and flavor.

Spend a day in Tuscany visiting the city of Siena, the castle of Monteriggioni and the medieval village of San Gimignano. With a private English speaking driver, you will enjoy greater flexibility in your itinerary with plenty of free time. Enjoy a walk through the historic center of Siena then have fun tasting the famous Chianti wine with a lunch in a family-run winery (tasting and lunch not included in the price) and then admire the view of the Tuscan countryside from San Gimignano where you can taste the best ice cream in Italy. Finish the tour with a visit to Piazzale Michelangelo before returning to Florence.

Whether you’re hoping to see the Leaning Tower of Pisa or want to take in San Gimignano’s medieval architecture, there’s a lot to experience in both locations. On this full-day private trip, meet your driver at your Florence accommodation and take in the Tuscan countryside as you ride, with two hours in each location to explore.

Exploring the Chianti countryside and its historic hill towns by public transportation is virtually impossible. With this private day trip, relax and enjoy the views as an expert local driver takes you across the rolling hills to San Gimignano and Monteriggioni. Explore the medieval towns at your own pace and relax over a wine tasting at a Chianti cellar before the ride back to Florence.

Enjoy this unforgettable High Level Tour and make memories of the landmarks. A day exploring the landscapes and artistic small towns that Tuscany can offer: • San Gimignano • Siena Wine and Light Lunch in the Tuscany countryside included! Upgradable with licensed local guide in Siena (if option selected) Pickup and dropoff will be at your accommodation. Worry-Free and Safe Private Tour Experience, operated only with: • Expert Professional English-Speaking Drivers • Selected local Expert Licensed Tour Guides • Welcoming by private licensed fully-insured air-conditioned comfortable Vehicles

- Very knowledgeable drivers with explanation about wine, food and general history of Tuscany. - Visit the town of Siena a Unesco World Heritage Site. - Lunch in a typical Trattoria or a wine Estate in the Chianti area. - Visit San Gimignano, the medieval "Manhattan" frozen in time.

Embark on a condensed yet captivating exploration of Siena and San Gimignano. Begin in Siena's heart at Piazza del Campo, marvel at the cathedral, and admire historic landmarks like Palazzo Salimbeni. Conclude your Siena visit to the Basilica of San Domenico. Transition to San Gimignano, starting at Piazza del Duomo with its iconic Collegiate Church. Climb Torre Grossa for panoramic views and stroll through Piazza della Cisterna. Explore the Civic Museum and meander along Via San Matteo. End the tour at Rocca di Montestaffoli for breathtaking views. For a more immersive experience, consider an optional lunch at a family winery, showcasing the best of Tuscan flavors. Indulge in farm-to-table dishes and local wine tastings amid the picturesque vineyards. Note that lunch with wine tasting is not included but can be added as an optional and delightful extension to your tour.

Discover the best of Tuscany on a private journey through its beautiful towns and landscapes. Travel from Florence with a professional English-speaking driver who takes the stress out of navigating. In Siena, meet a licensed local guide for a walking tour through medieval streets. Along the way you'll learn about the majestic cathedral and famous Palio horse race. Then, savor a leisurely Tuscan lunch with wine pairings at a family-run Chianti farmhouse, surrounded by vineyards and olive groves. End your day in the hilltop gem of San Gimignano, a UNESCO-listed village, where you’ll enjoy free time to explore artisan shops, climb the towers, or simply soak in the views. With private transport and a relaxed pace, this day offers an intimate and authentic way to experience Tuscany.

The Tuscan countryside is a gourmet paradise, but few transportation options keep many travelers limited to Florence. Explore Siena, home to a magnificent cathedral and the famous Palio horse race, and the storybook village of San Gimignano (a UNESCO World Heritage Site) during this small-group tour. A seasonal lunch and Chianti wine tasting at a family-run vineyard are included.

Seeing both San Gimignano and Siena in one day can be difficult to coordinate on your own. This guided day trip from Florence simplifies the journey, combining two of Tuscany’s most atmospheric towns into a single, well-paced itinerary. Travel through the Tuscan countryside with a guide providing insight along the way, then enjoy free time in each destination to wander medieval streets and take in the scenery at your own pace.

Getting around Tuscany by public transport can be daunting. Skip the hassle of coordinating train and bus schedules and cover two top Tuscan towns in a single day with this San Gimignano and Siena tour. Explore the medieval old town of San Gimignano and enjoy a wine tasting before continuing on to Siena. Skip the line to enter the magnificent cathedral and explore the sights, shops, and eateries at your own pace.

Discover the essence of Tuscany on this immersive tour that combines history, stunning landscapes, and exquisite flavors. Departing from Villa Costanza, journey to Monteriggioni, a medieval fortress town where cobbled streets and artisan shops await. After exploring its historical charm, indulge in a guided wine tasting at a picturesque Chianti winery, savoring local varietals and regional delicacies. Continue to a renowned family-run winery in San Gimignano for another rich tasting experience that reflects the region's winemaking passion. This tour promises a blend of cultural immersion and culinary delight, perfect for history buffs and wine enthusiasts alike. - Depart from Villa Costanza at 14:45 for a half-day adventure - Explore the medieval fortress-town of Monteriggioni with free time - Enjoy guided wine tastings and cellar tours at two charming wineries - Experience the richness of Tuscan terroir with local cuisine pairings

Begin your adventure in Pisa, where you'll have free time to explore the UNESCO-listed Piazza dei Miracoli. Marvel at the Leaning Tower, one of the most iconic landmarks in the world. Admire the Cathedral and the Baptistery, and take plenty of time for photos and local souvenirs. Head into the Chianti hills to enjoy a Tuscan lunch at a traditional winery. Your meal will be accompanied by a guided wine tasting of local varieties, offering a true taste of Tuscany's winemaking heritage. Enjoy free time in Siena, where you can stroll through medieval streets and admire the stunning Piazza del Campo, one of Europe’s most beautiful squares. Known for its shell shape and unique charm, it’s also home to the Palio di Siena, a famous bareback horse race held twice a year. Conclude your day in San Gimignano, a breathtaking hilltop town famous for its skyline of medieval towers. Explore its cobbled streets, artisan shops, and panoramic views. Don’t miss the chance to try its world-champion gelato!

Indulge in the perfect tour for those seeking to explore the Tuscan Countryside. Your private driver, at your disposal for the day, will guide you through the picturesque Tuscan hills adorned with historic olive groves, expansive vineyards and charming towns. Several quaint towns will be part of your itinerary, with Greve in Chianti standing out as the renowned "wine town". Here, explore typical shops offering "vino for sale" and visit the unique triangular square hosting the local market. A visit to a local vineyard awaits, where you will gain insights into the winemaking process and indulge in a tasting of various wines, followed by a delightful Mediterranean light lunch. San Gimignano, a UNESCO Heritage Site known for its medieval charm and iconic skyline of tall towers, will be a highlight. Enjoy a leisurely stroll along its streets, and do not miss the Duomo, adorned with frescoes covering its walls.

A peaceful bike ride from Chianti through Certaldo to the Etruscan town of San Gimignano. If you are not an avid cyclist and you just want to enjoy the countryside without sweating and getting too tired, this bike tour is a perfect fit for you. You will ride mostly downhill enjoying beautiful views of the Chianti wine region, allowing plenty of time for breathtaking photo stops. At the end of the ride you’ll enjoy the view of Certaldo followed by a visit of San Gimignano (UNESCO world heritage site). You’ll have 1.5 hours to experience the fantastic hilltop town and to try the world-renowned gelato, wild boar prosciutto/salame, delicious pecorino cheese, saffron and many more delicacies. At the end of the tour a wine tasting will complete the best day of your vacation in Tuscany. Distance: 13km (8miles). Total Elevation: 100m (330ft). Duration: 8 hours. Skill level: Beginner (suitable for occasional or casual cyclists). Number of participants: 2-7. Support vehicles: yes.

On our E-bike tour you will discover one of the most beautiful areas of Tuscany, the Val d’Elsa. We will cycle along one of the oldest roads from the Middle Ages, now a UNESCO World Heritage Site, the Via Francigena. This road connects Canterbury with Rome and has been abandoned for decades. Thanks to the breathtaking views you can enjoy along the road, the Via Francigena has recently been rediscovered. Before arriving in San Gimignano, the undisputed queen of the Val d'Elsa, we will ride our E-bikes up and down hills full of vineyards, olive groves and ancient medieval villages. In San Gimignano you will have 45 minutes to explore the town, take some pictures and taste some traditional Tuscan food. After lunch we will get back on our E-bikes to ride back to the starting point. Distance: 35km (21,7 miles). Total Elevation: 500m (1650ft). Duration: 7 hours. Skill level: Intermediate/Advance. Number of participants: 2-8. Support vehicle: no.

Let a professional guide be your designated driver while you enjoy the food and wine on this private tour of two of Tuscany’s most attractive walled towns: San Gimignano and Volterra. Start with a guided tour of Volterra plus a delicious local lunch. Next, visit San Gimignano, famed for its medieval towers and world-renowned gelato shops. Following a city tour, shop in the charming boutiques of the city center.

Chianti wine country is known for its magical scenery, but exploring the area can be tricky for out-of-town travelers. Leave traffic and navigation to your private driver as you sit back and enjoy the ride on this half-day wine-tasting tour. Savor both red (Chianti Classico) and white (Vernaccia) wines, capped off by the chance to explore the beautiful medieval town of San Gimignano.

In the heart of Chianti, 3 unforgettable Tuscan experiences in one perfect day: 1) Exciting truffle hunting adventure 2)Delicious fresh truffle pasta lunch 3)Exclusive Chianti wine tasting in a typical cellar winery Join us and discover the secrets of this ancient tradition! Enjoy a scenic drive through the rolling Tuscan hills, surrounded by vineyards and olive groves, to meet your expert truffle hunter. • Before the hunt, learn the rules and discover how truffle dogs are trained. • Then follow the hunter and his loyal dog into the woods for an authentic truffle hunt—an experience to remember! • Afterwards, relax in a charming wine cellar and savor a Tuscan lunch featuring truffle pasta and local specialties. Taste 3 premium Tuscan wines, including the renowned Chianti and Super Tuscan, with an expert introduction. Best time for this unforgettable adventure: from May to October. Tuscany... what else?

Discover the enchanting Chianti wine region and its picturesque rolling hills on this full-day tour from Florence. Explore the medieval village of San Gimignano, climb its tallest tower for panoramic views, and capture photos among the vineyards. Savor a homemade pasta lunch and taste five Tuscan wines, including Chianti and Super Tuscan, at a family-run farm in Badesse to complete your Tuscan journey.