Day Trips from Tuscany to Siena

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.

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.

Get a taste of Tuscan landscape, wine, and food on this full-day private tour from Florence. Led by an English-speaking driver, discover the regions of Chianti and Val d’Orcia, soaking up the local flavor with several wine tastings. Explore the charming towns of Castellina and Montepulciano, and savor a traditional Tuscan lunch at a farmhouse in Montalcino.

Explore the enchanting Tuscan countryside on this self-drive adventure with an electric Vespa. With a dedicated guided app, drive through Chianti’s winding roads, surrounded by vineyards, olive groves, and cypress trees. Discover charming medieval towns like Montefioralle and Greve in Chianti, and stop to feast on a delicious Tuscan lunch in a typical trattoria.

Escape Florence for a renowned Chianti Classico estate where pasta-making is a daily ritual. This experience blends professional culinary instruction with an evocative local legend. Before cooking, you’ll discover the story of the noblewoman and her seven maidens who protect these vineyards—a mystery reflected in the estate’s designer wine labels. In the kitchen, a Professional Chef guides you in crafting perfect egg tagliatelle, creamy Cacio & Pepe sauce, and authentic Tiramisù. The highlight is the "farm-to-table" banquet: a generous feast including a Tuscan appetizer platter, your handmade pasta, and a second course of "Pici" with artisanal ragù. The meal is elevated by a technical tasting of 5 premium wines (Vermentino, Chianti Classico, and Supertuscans). This half-day journey offers the perfect balance of hands-on learning, legendary storytelling, and high-end gastronomy, ensuring a return to Florence by late morning with memories and recipes to last a lifetime.

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.

Visit two of Tuscany's beautiful hilltop towns, plus enjoy tours and tastings at boutique wineries in Chianti and Montalcino on this small-group tour from Siena. All transport is included for a hassle-free experience, with free time to explore Pienza. Sample top Chianti, Brunello, and Super Tuscan wines, and relax over a Tuscan lunch featuring local specialties.

Discover the history of the Chianti region, visit Montalcino's medieval fortress, and enjoy a scenic drive through Val d'Orcia on this small-group tour from Siena. Taste Chianti Classico and Brunello wines paired with Pecorino cheese, bruschetta, salame, and extra virgin olive oil. Explore the historic cellar and learn about the wine production process in a boutique family-owned winery.

Cross the Tuscan hills in search of fine wine, local food, and unforgettable views. This small group tour from Florence takes in UNESCO heritage sites, charming medieval towns, and a landscape that captivated Renaissance painters. Stop in Montalcino for a lunch of local fare and a tasting of some of the best wines in the world. And head to Montepulciano to wander its picturesque palazzos and visit the historical wine cellars.

Escape far from the crowds and traffic—and enjoy an immersive way to explore the iconic Chianti countryside that few other visitors get to experience—on this small-group, full-day hiking tour from Florence. Ramble for 4 miles (7 kilometers) on trails through vineyards and olive groves to really soak up the scenery. Along the way, visit three wineries to sample up to 10 wines, and enjoy Tuscan specialties for lunch.

Semi-private tour to Discover the enchanting Chianti Classico region on a meticulously crafted wine tour that immerses you in Tuscany's lush vineyards and celebrated wineries. Enjoy scenic drives in a luxury minivan, visit two organic wineries, and indulge in a delightful lunch paired with exquisite local wines. Led by expert guides with deep local knowledge, this tour offers insights into the winemaking process from passionate artisans. Perfect for wine lovers and food lovers, this experience caters to small groups and ensures a personalized itinerary for a memorable day in Tuscany. - Enjoy a full 5-hour tour of the Chianti Classico region - Semi-private for a maximum of 7 guests. - Visit 2 organic wineries with exclusive tastings of Chianti Classico and supertuscans wines - Savor a delicious locally-sourced lunch at a winery - Travel in luxury transportation from Florence with an expert guide -Scenic roads for a great experience - No pressure on buy wines

This tour offers a unique opportunity to explore three iconic Tuscan cities—Florence, San Gimignano, and Siena—in just one day from Pisa. Experience Florence's Renaissance charm at Piazza del Duomo and Ponte Vecchio, the medieval allure of San Gimignano's Piazza del Duomo and Torre Grossa, and the Gothic splendor of Siena's Piazza del Campo and Cathedral. Enjoy free photography for 30 minutes to capture your memories. With convenient transportation between cities and expertly planned stops, this tour maximizes your time while providing a rich cultural experience. It's a perfect blend of history, architecture, and breathtaking scenery, ideal for travelers seeking to see Tuscany's highlights in a single day

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).

Enjoy a day trip to three of Tuscany’s most iconic destinations: Montalcino, home of the famous Brunello wine; Pienza, renowned for its Pecorino cheese; and Montepulciano, known for its prestigious Nobile wine. Travel through the UNESCO-listed Val d’Orcia aboard a premium air-conditioned minivan with an English-speaking driver and complimentary water. Small group experience, maximum 8 participants. Why choose us? • Guaranteed departures • Secure booking • 24-hour cancellation policy • Best rates guaranteed For operational reasons, the itinerary order may vary between Montepulciano and Montalcino.

Taste the famous flavors of Tuscany's wines and olive oils on this private tour from Florence. Travel through the Chianti region in a luxury tour vehicle, taking in the sights of the rolling hillsides covered with groves of olives and grapes. Take tours of several vineyards and learn about their production through guided commentary. Enjoy tastings of Chianti varietals and tuck into a tasty 3-course lunch with more wine.