Day Trips from Tuscany to Siena

we will make you experience Chianti as we do, in its beauty, goodness and simplicity, with fun and light-heartedness

Explore the charming medieval town of San Gimignano, known for its iconic towers and rich history. After soaking in the sights, savor a delightful lunch at the Torciano estate, where you can also enjoy a guided tour of the winery and taste exquisite wines. The journey continues to Siena, a city filled with stunning architecture and vibrant culture. Ideal for travelers looking to immerse themselves in Tuscany's beauty and flavors. - Visit the enchanting town of San Gimignano, famous for its towers - Enjoy a delicious lunch and wine tasting at the Torciano estate - Experience the rich culture and stunning sights of Siena - Perfect for wine lovers and cultural enthusiasts alike

Spend a day in the iconic landscape of the Chianti hills with a private tour from the Pisa countryside. Drive along avenues of cypress trees, vineyards, sunflowers and medieval villages. Visit the historic town of San Gimignano and admire its ancient towers, enjoy homemade pasta and taste the best wines of the Tuscan countryside at a typical farm. Itinerary: • Our driver will pick you up at your accommodation and take you through the rolling hills of Tuscany, among olive groves, cypress trees and vineyards, to the magnificent towers of San Gimignano, also famous for its white wine, Vernaccia. • Then we move to a typical family-run farm to discover the secrets of wine production and enjoy a lunch with homemade pasta, bruschetta, Pecorino cheese and 6 wine tastings. • On the way back we stop at a second family winery near San Gimignano for another tasting of Chianti, Sangiovese, Super Tuscan and more.

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.

Immerse yourself in the scenic Chianti Classico hills, without the hassle of driving, on a full-day private wine adventure from Florence. Discover the heart of Tuscany’s famous wine district, savoring organic wine tastings and enjoying a light lunch of authentic Tuscan delicacies at a typical farmhouse. Led by a guide, this tour is perfect for wine lovers eager to experience the charm and flavors of Chianti.

Fiat 500 represents the emblem of Italian Style. Shape, size and its unique charm make of this car a special and authentic symbol beyond it’s simple use as a vehicle. Ideal both on city’s tiny alleys and on the famous country-side windy roads. We will be visiting typical medieval villages, get in touch with local wine and food producers as well as artisans, and stop along the way to take some picturesque photos that will become indelible memories. An experienced tour guide will lead you around and show you the way as only a local can. The tour ends in a local farm where we will be hosted by a family that has been living there since centuries, producing their own wine, Chianti Classico. We will have the chance to visit the property including the cellar and then relax where a traditional Tuscan lunch will be served, all accompanied by their wines. Pick up and drop off from your accomodation in Siena included.

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

We will spend an entire day crossing the most characteristic and beautiful part of the Tuscan countryside: the Chianti. Here we will visit small villages and admire unique landscapes ... without forgetting to taste some good wine!

Discover the enchanting Chianti region on a 5.5-hour afternoon wine tour through Tuscany’s rolling hills and vineyards. Visit two local wineries and enjoy tastings of around seven wines, including white, red, and rosato varieties, while learning about traditional wine-making techniques during guided cellar visits. Along the way, sample regional products such as extra virgin olive oil and balsamic vinegar, and stop at a scenic panoramic viewpoint for beautiful photos of the Tuscan countryside. Round-trip transportation from Florence by GT coach or minivan and the assistance of an expert multilingual guide are included.

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.

La Gallinella’s Ecolodges are nestled among picturesque chestnut woods, olive groves, cherry orchards and other breathtaking vantages throughout the 4-hectare grounds. All Ecolodges are furnished with an en-suite bathroom, a private kitchen, beds, and other amenities for a truly relaxing glamping experience. Take a stroll in the tranquil shade of La Gallinella’s forested footpaths and listen to the sounds of the lush, Tuscan countryside. Walk among the idyllic olive groves and cherry orchards. Or simply sit back, relax, and enjoy a cold beverage in the comfort of your Ecolodge—at La Gallinella, reconnecting with nature has never been more glamorous. If you’re interested in exploring the surrounding areas, there is no shortage of outdoor activities to enjoy. Horseback riding, biking, hiking, and sailing are a few popular pastimes for locals of the area. Some of Italy’s most beautiful natural spas are only a few miles away.

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).

Your experience begins early in the morning with a free tour of Pisa, here you will have time to admire the magnificent Cathedral, the Baptistery, the Monumental Camposanto and of course the famous Tower of Pisa. Afterwards, we will move to a rustic winery in Chianti, on the slopes of San Gimignano, where you will be waiting for a typical Tuscan light lunch enriched by a tasting of good wine. After lunch you will discover one of the most beautiful medieval villages perched, San Gimignano, also known as the Medieval Manahattan for the many towers that distinguish it. We will then arrive in Siena, where our expert guide will lead us from Piazza del Campo, up to the Cathedral, crossing the most beautiful Contrade that characterize this city. At the end of the tour, there will be free time to enjoy a coffee and some shopping in the typical local shops. Our return to Florence will have as its scenery a magnificent sunset, a perfect conclusion to an unforgettable day spent in Tuscany.

Escape the hustle and bustle of Florence for a private tour of Tuscany’s medieval towns. Visit San Gimignano, known as the “Town of Fine Towers,” explore Monteriggioni’s perfectly preserved castle, and immerse yourself in the historic charm of Siena, a UNESCO World Heritage Site. From breathtaking views to centuries-old architecture, this tour provides a glimpse into the region’s rich past.

Escape the crowds and experience the best of Tuscany with this private shore excursion from Livorno or Florence. Travel in comfort from your ship or hotel with a private driver and enjoy a small-group walking tour of San Gimignano, led by a local expert. Discover medieval towers, artisan shops, and breathtaking views in this UNESCO-listed town. Enhance your day with an optional wine tasting and Tuscan lunch at a renowned Super Tuscan winery, where you’ll sample Vernaccia di San Gimignano and other local labels in an authentic countryside setting. After lunch, continue to Siena, one of Tuscany’s most enchanting cities. Enjoy free time to explore Piazza del Campo, admire the Siena Cathedral from outside, and stroll the historic streets at your own pace. This flexible experience can be tailored to your cruise schedule, with guaranteed on-time return. Perfect for travelers seeking a mix of history, beauty, and flavor in a single day.

Discover the charm, history, and flavors of Tuscany on this private full-day tour by luxury minivan, led by a licensed English-speaking driver-guide with deep local knowledge. Visit two UNESCO World Heritage sites—Siena, with its stunning Gothic cathedral and famous Piazza del Campo, and San Gimignano, known for its medieval towers and artisan shops. Enhance your experience with an optional wine tasting and full Tuscan lunch at a family-run winery (not included, but highly recommended). Enjoy a fully customizable itinerary with convenient pickup and drop-off from your accommodation in Florence. Highlights: -Private full-day tour for up to 7 travelers -Explore Siena and San Gimignano, both UNESCO World Heritage Sites -Travel in comfort with a luxury minivan with Wi-Fi and licensed English-speaking driver-guide -Optional wine tasting and lunch at a local winery (not included, but highly recommended) -Hassle-free pickup and drop-off from Florence

Lilium Travel Florence offers a full-day, 9-hour journey through the heart of Tuscany with a private van tour (max 8 pax) from Florence. First, you’ll visit San Gimignano, the "Town of Towers," a stunning medieval gem and UNESCO World Heritage site. Explore its narrow streets, admire the well-preserved towers that once symbolized wealth and power, and soak in panoramic views of the surrounding Tuscan countryside. Next, head to the village of Monteriggioni, a perfectly preserved medieval fortress with its iconic walls and towers still standing proudly. Wander through the town, feeling as if you’ve stepped back in time. The final stop is Siena, famous for its unique medieval architecture and the breathtaking Piazza del Campo, home of the historic Palio horse race. Enjoy time to explore its cobbled streets, visit the stunning Siena Cathedral, and relax in one of its charming cafes. With ample free time at each location, this tour offers a perfect blend of history, culture, and relaxation.

Discover the medieval charm of Monteriggioni on a private luxury e-bike experience, ride scenic Tuscan roads, enjoy a curated lunch paired with fine wines, and end with an exclusive winery visit scheduled just for your group. More than a bike tour, this is a curated Tuscan experience for couples, families, and small groups seeking an authentic, relaxed, and elevated way to explore. Led by a professional local cycling guide, far from crowded routes, your ride is tailored to your pace, allowing you to fully enjoy the landscape and timeless atmosphere. Premium e-bikes ensure a smooth, accessible ride with minimal effort. The experience concludes with a refined lunch and wine pairing in a carefully selected winery, featuring a private dining room reserved for you and a private cellar visit without overlapping guests. A seamless Tuscan day blending cycling, culture, landscape, and fine wine — designed for comfort, privacy, and authenticity.

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.

Experience the breathtaking Chianti hills on a day trip filled with stunning landscapes and rich culture. Begin with a visit to the UNESCO-listed city of Siena, renowned for its exquisite architecture. Enjoy a delicious lunch at a traditional Tuscan farmhouse, featuring homemade pasta and five tastings of the finest Chianti wines. Then, discover the secrets of local wine production in a picturesque setting.

Enjoy a full-day journey from Florence through the rolling Tuscan hills to visit San Galgano, Pienza, and Montepulciano. Immerse yourself in the enchantment of San Galgano, a place where time seems to stand still. Here, nestled among the hills, stands the evocative roofless Abbey—a Gothic masterpiece that has defied the centuries, offering unforgettable views under the open sky. The journey continues with a visit to the nearby Hermitage of Montesiepi, home to the legendary Sword in the Stone. Next, explore Pienza, a splendidly preserved Renaissance village boasting breathtaking views of the Val d'Orcia. Finally, in Montepulciano, stop at a renowned local winery to taste the region's finest wines, perfectly paired with authentic Tuscan specialties.

Escape the city and experience the very best of Tuscany on a full-day journey through its most iconic destinations. Travel comfortably from Florence to discover the medieval charm of Siena, the famous towers of San Gimignano, the rolling vineyards of the Chianti countryside, and the world-renowned Leaning Tower of Pisa. Stroll through UNESCO World Heritage Sites, admire spectacular Renaissance and medieval architecture, taste authentic Tuscan wines and local specialties at a traditional winery, and capture unforgettable views of Tuscany's picturesque landscapes. Whether you're fascinated by history, passionate about Italian culture, or simply looking to experience Tuscany's timeless beauty, this tour offers the perfect combination of historic cities, scenic countryside, and authentic local flavors—all in one unforgettable day.

Explore Siena and San Gimigano on our private Shore Excursion, travelling in the comfort of an air-conditioned vehicle. Discover the highlights of Siena, admire the marvelous Tuscan landscape, relax in the hilltop village of San Gimignano and taste ocal wine. Your english speaking driver greets you at your cruise ship at Livorno Port and chauffeurs you to your first destination, Siena. You will have about 2 hours of free time to explore the town, a true jewel of Tuscany. Continue your day visiting San Gimignano. Famous for its skyline of tall Medieval towers, here you will have free time to explore the main street full of typical shops, have a look at its splendid Cathedral and medieval palaces, and enjoy a wine tasting! At the end of the wonderful Siena and San Gimignano Shore Excursion, your driver will chauffeur you back to your cruise ship at Livorno Port. Get on board and enjoy the tour!

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