Day Trips from Tuscany 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.

VEHICLES BOOKED: Standard Reservation includes 1 QUAD for every 2 participants. A Reservation for 2 people includes 1 Quad shared by a driver and a passenger. This unique experience allows you to visit the most interesting places in the Val d'Orcia and Montepulciano crossing country roads to admire nature and works. The departure begins and ends in my Farm, next to the Sanctuary of the Madonna della Querce in Montepulciano. Here I breed Cinta Senese pigs, a type of black pig with a white belt, of Tuscan origins and very ancient. We will take a short walk among the olive trees and the vineyard to get to the pigs, which are free, separated by an electric fence. We can walk with them, touch them and take pictures. Lunch is included and includes a menu with : Bruschetta, ribollita in winter and panzanella in summer, platter with cold cuts from our production, pecorino cheese from Pienza with jams, cantucci and vinsanto, water, house wine.

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.

Visit Monteriggioni, San Gimignano, and more on a customizable 8-hour private tour. After pickup from your Siena hotel, discover the Tuscan countryside in a luxury vehicle, complete with complimentary WiFi and refreshments. Given that you’re in the heart of Chianti Classico, a tasting at a local winery is highly recommended. But you're free to pick and choose which locations you’d like to visit and your guide will happily oblige.

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.

Kick off your day with a comfortable ride through the stunning Tuscan countryside. First, we’ll arrive in Siena, one of Tuscany’s most beautiful towns. Explore Piazza del Campo, famous for the Palio di Siena horse race, admire the breathtaking Duomo (Cathedral), and wander through the charming, narrow streets of the historic center. Wine Tasting & Light Lunch Next, we’ll head to a renowned winery for a light lunch paired with an amazing wine tasting experience. A sommelier will guide you through five exceptional wines, plus an olive oil tasting. After lunch, we’ll continue our journey with a spectacular drive through the rolling Vernaccia di San Gimignano vineyards, home to Tuscany’s most famous white wine. Stop in San Gimignano you’ll have free time to explore this medieval gem, known for its 14 towers dating back to the 13th century. The town’s atmosphere will transport you back to the Middle Ages! And of course, you can’t miss the world’s best gelato at Gelateria Dondoli.

This exclusive private wine tour takes you from Cortona to the heart of the Chianti Classico Black Rooster, an iconic wine area rarely reached from this part of Tuscany. Travel in comfort with a local professional driver and enjoy a personalized journey through one of Tuscany’s most celebrated wine landscapes. The experience includes visits to three carefully selected Chianti Classico DOCG wineries, where you will enjoy guided cellar tours and premium wine tastings. Each winery offers a different perspective on the Black Rooster tradition, allowing you to discover the diversity, history, and craftsmanship behind authentic Chianti Classico wines. A traditional Tuscan lunch is included, perfectly paired with local wines and seasonal products, for a complete and immersive Chianti experience. Designed for travelers seeking authenticity, privacy, and high-quality wine experiences, this tour combines culture, scenery, and exceptional flavors in a relaxed and exclusive setting.

Slow down and experience Tuscany at your own pace in this refined side of Tuscany with a private Val d’Orcia slow experience, designed for those who value beauty, comfort, and unhurried moments. No rushing, no tight schedules—just time to enjoy Tuscany. Begin with a traditional Italian breakfast in the quiet village of Monticchiello, featuring homemade pastries and freshly brewed coffee. Travel through the iconic rolling hills of the Val d’Orcia, stopping in elegant villages such as San Quirico d’Orcia, far from the crowds. Enjoy a curated Tuscan picnic in nature with artisanal cheeses, cured meats, fresh bread, and your choice of wine, beer, or water—set against one of Italy’s most breathtaking landscapes. In Bagno Vignoni, take time to explore or simply unwind. Relax under the trees and experience a peaceful siesta in complete tranquility. * Private, refined slow tour * Italian breakfast and curated picnic * Scenic villages and countryside * Time to relax and disconnect

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.

Discover the wonders of Chianti and San Gimignano on a private day tour from Lucca. This customized excursion is perfect for travelers seeking an authentic Tuscan experience. With a private chauffeur at your disposal, you’ll immerse yourself in the charming Chianti countryside, enjoy tastings at renowned wineries, and witness skilled artisans at a terracotta workshop. Later, explore the UNESCO World Heritage site of San Gimignano, with its iconic medieval towers.

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.