Day Trips from Florence to Siena

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.

Spend a day in the iconic landscape of the "Hills of Chianti" with a private tour. Pass between avenues of cypress trees, vineyards, sunflowers and medieval villages. Visit the historic village of San Gimignano and admire its ancient towers, enjoy homemade pasta and savor the best wines of the Tuscan countryside in a typical farm. Itinerary: • Our driver will pick you up at your location and take you on a journey through the rolling hills of Tuscany. We will move among olive groves, cypress trees and vineyards until we see the magnificent towers of San Gimignano. San Gimignano is also famous for the white wine Vernaccia, produced from the ancient Vernaccia vine. • Later we will move to a typical Tuscan family-run farm, to understand the secrets of wine production and enjoy a lunch with homemade pasta, bruschetta, percorino cheese and 6 wine tastings. • On the way back we will stop in a second typical cellar for a second tasting of Chianti, Sangiovese, Super Tuscan and more...

Experience the best of Chianti from its historic hill towns and rolling landscape to its storied wineries in a single day with this private driving tour. Save hours with a dedicated driver, leaving you time to fit in visits to both San Gimignano and Monteriggioni. Break up your sightseeing with a wine-tasting lunch at a Tuscan farm and cap off your day with a Chianti winery tour and tasting.

Discover the best of Tuscany in just one day with a private tour, ending with a three-course dinner and and local wine tasting in amongst the vineyards of Chianti. Watch the rolling hills and olive groves from the comfort of your private car or minivan, before exploring some of Tuscany’s most beautiful spots–including historic San Gimignano and Torre Grossa known for its stone towers, then watch sunset from a 14th-century hilltop fortress.

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. Hassle-free transport from Florence to see Siena, San Gimignano, and Pisa Delve into the history and architecture of Siena with a guided walking tour Sample tagliatelle pasta, salami, cheeses, and local wines at lunch Free time to explore San Gimignano and Pisa’s Piazza dei Miracoli

Explore Tuscany’s stunning landscapes and rich history on a full-day trip from Florence. Visit the medieval town of Monteriggioni, the UNESCO World Heritage site of San Gimignano, and the historic city of Siena. Enjoy wine tastings at a vineyard, paired with local delicacies and artisanal olive oils, enhancing your culinary adventure. With ample time to wander charming piazzas and cobblestone streets, this tour is perfect for history buffs and wine enthusiasts alike. - Visit iconic medieval towns: Monteriggioni, Siena, and San Gimignano - Savor wine tastings paired with local Tuscan delicacies - Travel comfortably in an air-conditioned minivan - Enjoy free time to explore at your leisure in each town

Avoid the hassle of trying to navigate your way around the Tuscan countryside and visit two top wineries in a single day with this small-group Chianti wine tour. Leave the driving to a professional and sip worry-free as you stop to sample local reds and whites at traditional cellars in the hills of Tuscany. Learn more about the area's wine-producing history and culture, plus enjoy tasty snacks while taking in views over the Chianti countryside.

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

Chianti is globally renowned for its wines, but getting there—and getting around—requires private transportation. Enjoy behind-the-scenes visits to two historic wineries during this half-day wine-tasting tour. Admire stunning scenery and learn to taste wine like a pro as you explore the vineyards and wine cellars of two historic estates. Then sit down to a locally sourced Tuscan dinner, with the sun setting over the hills of Chianti as your backdrop.

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.

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.

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.

Treat your senses to a memorable day in the world-famous Chianti wine region on this private tour from Florence. Travel in a luxury minivan through a landscape of historic vineyards, rolling hills and medieval villages, with a private driver at your disposal throughout the day. Taste renowned Chianti wines and authentic Tuscan cuisine at estates of your choosing, or let your local driver make suggestions for the best places to wine, dine and explore.

Trade the busy streets of Florence for the ancient vineyards, medieval villages, and scenic landscapes of the Chianti wine region on this half-day tour. Let a knowledgeable local driver take you to some of the area’s best family-run wineries, where you can learn about traditional production methods and taste the local bounty like extra-virgin olive oil and renowned wine varietals like Chianti Classico. The private tour can be customized to suit your interests, such as a stop for an authentic Tuscan lunch at a local farm.

Experience the treasures of Tuscany on a private day trip from Florence. Travel by luxury minivan through countryside full of historic vineyards, medieval villages, and olive groves. Visit the charming medieval city of Siena and the town of Montalcino. Your professional, English-speaking driver shares local history and can recommend the best places to visit, shop, and dine for a customized experience.

Get a personal introduction to Siena and Chianti with a full-day, private tour from Florence in a luxurious van. Stroll Siena’s gothic streets with a local guide, and discover the art and black-and-white architecture of its UNESCO-listed historic center. Explore rolling vineyards and olive groves then taste your way through famous wineries, family cellars, local olive oils and aged balsamic vinegar.

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.

Experience the true flavor of the Tuscan countryside—and enjoy wine tasting without designating a driver—on this Chianti wine tour from Florence. Visit local wineries in scenic villages to sample revered Tuscan wines and learn winemaking secrets. Alternatively, enhance your day with a morning cooking class preparing traditional Tuscan recipes paired with premium wines.