Day Trips from Florence to Siena

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.

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

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).

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.

Immerse yourself in Tuscany’s charm with a tour from Florence! Begin your adventure in Pisa, where you’ll marvel at the Piazza dei Miracoli, Duomo, Baptistery, and the Leaning Tower of Pisa. Next, visit a Chianti Classico estate for a sommelier-guided wine tasting and a delicious lunch featuring local specialties. Continue to Siena for a guided walk through its historic gems like the Duomo and Piazza del Campo. End your day with a stop at Monteriggioni Castle before returning to Florence.

Enjoy personalized attention as you explore Siena and San Gimignano on this 6-hour private day trip from Florence. Skip the hassle of renting a car, as this tour provides round-trip transportation to both locations. Hotel pickup and drop-off is included.

Nothing says wine like Tuscany’s Chianti region, but it takes local knowledge to find the best wineries. Enjoy two exclusive wine tastings, topped off by a Tuscan lunch, during this private day trip from Florence. Learn the secrets behind the winemaking process as you go, and tour vineyards, cellars, and more. You’ll have time to browse traditional artisan workshops, too.

One full day of a beautiful guided sightseeing tour driving through symmetrical vineyards, olive trees, wooded groves, stone farm houses, late Renaissance villas and old villages, castles and medieval hamlets.

Visit one of Tuscany’s most respected wine regions on this tour from Florence to Brunello di Montalcino. In a private, air-conditioned car with a guide, drive first to Montalcino, a hilltop medieval walled city to explore the ancient town. Next, visit family-owned wineries in the Brunello countryside like Poggio Rubino and Capanna. Your guide will also take you to see the beautiful Abbey of Sant’Antimo, which is thought to date back to the sixth century.

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.

Cruise through Tuscan wine county in true Italian style — behind the wheel of a vintage Fiat 500. Learn how to drive the classic Italian car with a brief lesson, then hit the road with a private guide for a joy ride along scenic country roads. Stop at a typical Chianti village, a medieval hamlet, and an antique farmhouse, where you'll be treated to a homemade lunch and tasting of wine, grappa, and olive oil.

Get ankle deep in Tuscan tradition on a half-day grape stomping tour from Florence. You’ll explore the history and modern practices of winemaking. After tromping on the locally grown grapes, replenish your strength with a homemade lunch and wine tasting, and explore the hamlet of Castellina in Chianti before returning to your accommodation.

Discover the Tuscan countryside and cuisine on a private bike tour from Florence. After a transfer from your hotel, follow your guide as you pedal through the world-famous Tuscan landscape on an electric bike, to avoid becoming fatigued on the famous hills. The scenic journey takes you to a family farm where you enjoy a gourmet lunch prepared using local ingredients. The culinary experience continues with wine and olive oil tastings, before a leisurely ride back to the starting point.

Experience the hidden beauty of Tuscany like never before—aboard a Land Rover Defender, journey through the region’s legendary "strade bianche" (white roads), the secret gravel paths winding through vineyards, olive groves, and deep forests. Your journey includes three winery visits, each offering a unique perspective on Chianti Classico and its appellations. The experience culminates in a traditional Tuscan lunch, where authentic flavors meet world-class wines, creating a true taste of Tuscany.

Set out on a hunt for the elusive truffle on this private tour from Florence. Traverse the forest with an official truffle hunter and his dog to learn everything there is to know about this delicacy. After you work up an appetite, sit down to a delicious 3-course truffle lunch accompanied by wine from a local farm.