Top Siena Full-day Tours

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.

Visit San Gimignano and Volterra the easy way from Siena, on an intimate small-grop tour. Head to the hilltop town of Monteriggioni, then stop for a while in UNESCO World Heritage–listed San Gimignano, with its medieval towers and views over the Tuscan countryside. Drop into an alabaster workshop in Volterra, then indulge in a rustic lunch at a Tuscan farm. Learn about local history and culture along the way.

Take a day excursion to San Gimignano, Chianti, and Montalcino to experience the charm of the Tuscan countryside. Savor the best local blends during a wine tasting at a renowned Chianti winery. Optional lunch for an authentic gastronomic experience. Begin your full-day journey by seeing San Gimignano, well known as the City of Fine Towers. With your tour guide's insights, take advantage of your free time to explore the historical center and its artisan stores. Explore the birthplace of Vernaccia, the renowned white wine that is regarded as Italy's first DOCG wine, after that. Enjoy a sample of Chianti and you can choose to buy the optional lunch at a nearby winery. Discover the UNESCO World Heritage Site of Val d'Orcia before continuing on to Montalcino, which is famous for its panoramic vistas of Brunello grapes. Finish your tour by visiting a local wine cellar to experience the renowned Brunello di Montalcino.

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.

Avoid the hassle of planning routes between scattered wine towns and booking separate tastings on your own with a guided day trip from Siena. This experience connects the flavors of Montepulciano and Pienza with the scenic landscapes of Val d'Orcia, letting you move easily between villages without logistics stress. Spend your time enjoying wine, local food, and countryside views at a relaxed pace.

Explore Tuscany outside Siena on this small-group day trip, visiting San Gimignano and Montalcino. Don't worry about hiring a car, as all transportation is arranged. Take a break from the city as you discover medieval architecture and scenic views of Tuscany, with ample free time in each of the hill towns. The tour also includes a visit to a Montalcino winery, with the opportunity to sample Chianti and Brunello di Montalcino.

If you've only got limited time in Siena, make sure you maximize your experience of the Tuscan hot spot on a sightseeing tour that includes skip-the-line entry. An expert guide gives you an insider's view of this UNESCO World Heritage-listed town. Linger for a while in Piazza del Campo and stroll the streets with your guide, learning about the history of the place and leaving the navigating to someone else. Visit the Duomo, Siena's stunning cathedral, and stroll right in thanks to your skip-the-line ticket.

Explore southern Tuscany on a full-day tour from Siena through the scenic Val d’Orcia, combining food, wine and history. In the Montepulciano area, enjoy lunch at Vecchia Cantina di Montepulciano, outside the historic town centre. Savour a Tuscan appetizer, pasta with ragù or lasagna, and cantucci with Vin Santo. A vegetarian menu is available. Taste three wines from Cantina del Redi: Riccio Toscana Bianco IGT or Nobile di Montepulciano, Briareo Nobile di Montepulciano Riserva, and Vin Santo. Continue to Pienza, the Renaissance town known for its panoramic views and artisan shops, with free time to explore. Finally, visit Montalcino, home of the famous Brunello di Montalcino, before returning to Siena through the Tuscan countryside.

Leave the planning and driving to someone else on this daylong winery tour specializing in Brunello di Montalcino—a wine produced in the vineyards around the town of Montalcino. Visit 2 historic wine cellars in Montalcino and vineyards, have lunch in Montalcino a winery in the hill town of Montalcino itself.

Spend a day sipping one of Italy’s top wines, Brunello di Montalcino, on this trip from Siena to Montalcino. Travel first to a small winery to explore the vineyards and cellars and taste the famous Rosso and Brunello di Montalcino wine. Then, visit a family-run winery in Montalcino, where you tour the grounds and sit down for a classic Tuscan meal with more wine. Visit the Abbey of Sant'Antimo before tasting even more wine at your third and final winery of the day.

Maximize time spent in Tuscany with this full-day small-group tour of Pisa and Lucca departing from Florence. Learn about Renaissance architecture from your guide and taste Tuscan wines in a small wine shop. Climb Pisa’s famous Leaning Tower (entry is included) and explore the city independently with free time before continuing on to Lucca to see the old town center on foot.

Avoid the hassle of organizing transport and winery visits in Tuscany on your own. This small-group experience simplifies a day in Chianti, combining scenic travel with curated tastings at local wineries and time to explore Monteriggioni’s medieval charm. Enjoy a relaxed, well-paced outing that lets you focus on the region’s flavors and landscapes rather than the logistics.

Avoid the stress of navigating winding country roads or unfamiliar public transit on your own and instead discover the fine wines and rich historical heritage of Chianti on this full-day trip from Siena. Travel through the Tuscan countryside to Castello di Brolio in the heart of the Chianti wine country for guided tasting sessions and a traditional Italian lunch. Enjoy the intimate atmosphere of a small group capped at only eight people.

Hop on a full-day private tour to Florence and San Gimignano from Siena. Your adventure kicks off with a drive from Siena to Florence to explore the city center. Take a guided walking tour of the historic center and see key landmarks, including the Duomo, the Uffizi Gallery, and the Ponte Vecchio. Then, it's off to experience the medieval town of San Gimignano, known as the "medieval Manhattan."

With no train station and spotty bus service, San Gimignano can be a hassle to reach from Siena. On this small-group tour, sip world-class wine and watch the sunset over Chianti and San Gimignano with stress-free transportation. Led by an expert guide, explore the medieval town of Monteriggioni and visit Chianti wineries for tastings. Then, head to the UNESCO-listed San Gimignano to see the sunset as you savor a traditional Tuscan dinner in a farmhouse overlooking the hills.

See Tuscany in classic Italian style by exploring the bucolic region in a vintage Fiat 500. Take the wheel of the classic Italian automobile then ride to the stunning hilltop town of Monteriggioni, cruise through the rolling hills of Chianti, and stop at a local vineyard for a hearty lunch of local fare.

Enjoy a private tour of two of Montalcino’s most exclusive wineries, taste their award winning wines and visit their winemaking facilities. Our native English speaking guide will be with you throughout your unforgettable experience and will take you to lunch at one of the regions top restaurants.

Discover Siena's perfectly preserved medieval splendor with our self-guided audio tour app, allowing you to explore this Tuscan jewel at your own pace. Begin at the magnificent Piazza del Campo, the shell-shaped square that hosts the legendary Palio horse race and remains the heart of Sienese civic life after seven centuries. Marvel at the soaring Torre del Mangia and the Gothic grandeur of the Palazzo Pubblico, then ascend to the heavenly Duomo where Pisano's pulpit and the Piccolomini Library showcase Renaissance mastery. Wander through the contrade neighborhoods where medieval rivalries still define local identity, their fountains, flags, and parish churches marking territories unchanged for centuries. Discover the Pinacoteca's golden altarpieces and the Basilica of San Domenico where St. Catherine's head is reverently preserved, then lose yourself in the winding vicoli that reveal unexpected piazzas and artisan workshops.

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.

Stroll the charming Medieval streets of a Tuscan hill town with this 2-hour private tour of Siena. Learn about Siena's hidden gems from a knowledgeable guide in between visits to its most popular sights.

Embark on an adventure that will take you through the fascinating hills of the Chianti, crossing the iconic gravel roads of the Eroica, revealing, in a slow and contemplative way, an area rich in food and wine traditions, cradle of the famous Chianti Classico wine (tasting included) and proud of its tradition and culture linked to the long rivalry between Siena and Florence. In addition, the experience includes a guided tour of one of Chianti's most characteristic castles, the castle of Brolio, from which you can take in magnificent panoramic views to the vineyards and the city of Siena. To experience the most out of the territory, we'll book lunch at a local family owned restaurant (or in the Eroica Caffeteria) where you, in addition to enjoying its tranquility and warm welcome, can savour the dishes of the Tuscan tradition. The way back is mainly descending and the guide will stop in magnificent sightseeing spots before getting back to the starting point.

Tour with a certified sommelier guide expert on Brunello. Discover Tuscany with local expert out of beaten path. learn the history of Brunello wine making and visit historical wineries.

IF YOU ONLY HAVE ONE DAY IN LIVORNO, THAT'S THE BEST TOUR YOU CAN DO, OUR VEHICLES REACH ANY RESTRICTED PLACE AND WE TAKE OUR CUSTOMERS INSIDE THE HISTORICAL CITY CENTER