Top Siena Full-day Tours

Explore Tuscany beyond Florence or Siena with a full-day wine tour. Get picked up at your hotel for a small-group tour to visit local wineries and relax over lunch in the town of Montepulciano. Learn about how wine is made and taste regional specialties including Brunello. Meet the people behind the wine without the hassle of a rental car or navigating between wineries.

Discover Tuscany's stunning landscape, culinary delights and UNESCO-listed sites on a day trip to Montepulciano and Pienza from Siena. Led by a local guide, admire the architectural gems of the Val d'Orcia region and stop at a dairy farm for lunch and samples of salty Pecorino cheese. Conclude your trip in the scenic hill town of Montepulciano, with an optional visit to a winery. Group size is limited to eight people, ensuring personalized attention from your guide.

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 historic wine cellars and vineyards, have lunch in a winery in the hill town of Montalcino itself, and visit a winery in the nearby Nobile di Montepulciano area for good measure.

Get medieval on this guided tour from Sienna to San Gimignano and Volterra. Head to the marvelously diminutive hilltop town of Monteriggioni and then stop for a while in UNESCO world Heritage-listed San Gimignano with its plethora of medieval towers and commanding views over the Tuscan countryside. Finally, spend some time in an alabaster workshop in Volterra before indulging in a rustic lunch at a Tuscan farm. This small-group tour is limited to just eight people, ensuring plenty of personalized attention from the guide. 

Visit San Gimignano, Monteriggioni, and Montalcino on a day trip from Siena, and discover medieval architecture, wine, and stunning views of Tuscany. With ample free time in each of the hill towns, the tour also includes lunch at a Monteriggioni winery plus samples of Chianti and Brunello di Montalcino wine.

See the hills of Tuscany in true Italian style with this action-packed day trip on a Vespa scooter from Siena. Set off on your scooter through the Tuscan countryside, your guide leading the way, as you and other scooter-riding participants make your way to a Chianti winery for lunch. Tour the vineyards and cellars, sample some wine and indulge in an antipasto lunch before heading back to Siena.

Taste your way through Tuscany with this full-day wine tour of Montalcino, Pienza, and Montepulciano from Siena. Visit the charming town of Pienza and stop for one wine tasting each in Montepulciano and Montalcino.

Discover the fine wines and rich historical heritage of Chianti on a full-day trip from Siena. With a knowledgeable guide, travel through the sublime Tuscan countryside and visit castles cradled by rolling green hills and sprawling vineyards. Visit Castello di Brolio, the esteemed birthplace of Chianti wine, and delve into the opulent chambers of Castello di Ama. Pleasure your palate with fine samples of Chianti Classico wine during tasting sessions and feast on a traditional Italian lunch during your tour. Enjoy an intimate atmosphere on this small-group tour, limited to only eight people.

When visiting Florence, spend a delicious day winery hopping in the renowned Chianti wine region. Visit three of the best estates for tastings of Chianti Classico and other top varietals, plus a gourmet lunch of Tuscan specialties. There's also time to soak up countryside culture and history with a stop in San Gimignano or Monteriggioni, two of Tuscany’s best-preserved medieval towns.

Drench yourself in the fabled Tuscan countryside on this private, day-long hiking tour from Siena. Meet your expert guide in Siena and then drive in a comfortable minivan to the trail where you perambulate through verdant vineyards, rustic villages, and over the classic rolling hills of Tuscany. Stop halfway along the hike to indulge in a classic lunch of Tuscan treats and then travel via minivan to the town of San Gimignano, known as the ‘medieval Manhattan’ for its many gothic towers that form a medieval skyline in the 21st century. 

See Tuscany in classic Italian style by exploring the rustic region via a vintage Fiat 500, the classic, beloved and diminutive Italian automobile. Get picked up at your hotel in Siena and then ride to the stunning hilltop town of Monteriggioni, cruising through the rolling hills of Chianti along the way. Stop at a local vineyard and sample some delicious Italian wines with a hearty lunch of local fare. Follow the guide in a caravan. The number of participants on this small-group tour is limited to just ten, so you’re sure to get plenty of personalized attention from the guide.

Get up close and personal with Tuscany’s ineffable scenery, and explore with ease, on a full-day tour by electric bike. Meet your guide in Siena and travel by van into the Chianti hills, where you’ll receive your bike and helmet and will get familiar with the gear. With just a small group for company, set off on a tour of the countryside, visit a restored monastery, and head to a local winery, where you can enjoy a traditional meal and generous wine tasting.

Explore southern Tuscany with your own private guide on a full-day wine and food tour from Siena. Visit Pienza, Val d'Orcia, Montalcino, and more as you take in small towns, a 14th-century monastery, and sample Brunello di Montalcino, the famous wine of the region. Ride in comfort in a luxury Mercedes vehicle with a private guide who shares the best of the region.

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 Mercedes 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.

Experience the best of Tuscany—cheese and wine, of course!—on this private tour from Siena. You’ll admire fabulous scenery in the Val d’Orcia, learn about cheese making during a tour at an organic dairy farm, visit the World Heritage–listed town of Pienza, and enjoy tastings of the region’s renowned Brunello wine during a cellar tour at a winery in the hilltop town of Montalcino. With a privately guided tour, enjoy a more personalized experience.

Enjoy this unforgettable High Level Tour and make memories of the landmarks. A day exploring the landscapes and artistic small towns that Tuscany can offer: • San Gimignano • Monteriggioni • Siena Wine and Light Lunch in the Tuscany countryside included! Upgradable with licensed local guide in Private option. Pickup and dropoff will be at your accommodation. Private or Shared Tour available options. Worry-Free and Safe Private Tour Experience, operated only with: • Expert Professional English-Speaking Drivers • Selected local Expert Licensed Tour Guides • Welcoming by private licensed fully-insured air-conditioned comfortable Vehicles

The beautiful and untouched landscape is the absolute protagonist in Valdorcia. This area of Tuscany boasts of endless rolling hills covered with grain or sunflowers, a rich green valley which encompasses the Orcia river. Explore the South of Tuscany and visit the Medieval town of Cortona. Cortona is a traditional walled Etruscan town. Sitting at about 600 metres above sea level, it offers spectacular views over the surrounding valley and Lake Trasimeno. Ramble through the vineyards and visit the "Underground Wonders" of Montepulciano (The Historical Cellars of the city). Have lunch and a delicious wine tasting inside the Historical Cellars with cheese, ham and the best wines of our Region. 09.00 AM: Our Driver-escort will pick you up at your location (hotel or apartment) 10.30 AM: Visit the city of Cortona 13.30 PM: Lunch and wine tasting in Historical Cellar 15.00 PM: Visit the Medieval city of Montepulciano 16.00 PM Return at the hotel

When your cruise ship docks in Livorno, benefit from a private full-day tour of Siena and Florence that covers the top attractions efficiently. Drive across Tuscany to see the Duomo in Siena, the Duomo in Florence (Cattedrale di Santa Maria del Fiore), and take a walk across the Ponte Vecchio bridge. Stop into the Mercato del Porcellino to browse their Italian leather goods, before returning to Livorno.

Maremma is considered the new Eldorado for its powerful and elegant wines, wild and shining landscapes. The typical local cuisine is Mediterranean. The people of Maremma are the most outspoken in Italy. History will take us back in time to the Etruscans.

• During the 8-hour guided tour you'll have the opportunity to visit some of the most famous vineyards, see their wine cellars and taste excellent wines.  • Visit small villages such as Greve, Castellina and Radda in Chianti and ancient castles, hidden among green hills and surrounded by vineyards and olive groves. • This tour is a perfect combination of culinary delights, arts and culture. This private tour can be customized from locations you visit to the starting time of the tour.

Enjoy a unique wine tasting! Transfer by air conditioned minivan from Siena to Montalcino area to discover Brunello di Montalcino famous wine. Guided visit of a famous wine cellar and its famous Brunello Wine Museum, lunch in taverna with a tuscan delicious meal combined with this excellent wine. An unmissable experience in the wonderful Tuscany countryside.

Not far from Siena, Chianti is a picture-postcard corner of Tuscany covered in rolling hills punctuated by rows of grapes, olive groves and farms where some of Italy’s most renowned wines are produced. Escorted by a private driver, you will embark on a scenic road trip through this stunning wine district, stopping at local wineries to taste the best regional wine varieties. Stops include a wine tasting session at Volpaia, an ancient hamlet dating back to the 10th century where pilgrims used to stop on their way to Rome, and a visit to Vignamaggio, an historic estate that has been producing wine since the 15th century. Here you will enjoy a delightful dinner with some of the region’s delicacies surrounded by the gorgeous scenery of a Tuscan sunset.

Visit 2 unique wineries close to Siena on this self wine tour. Depart by 9 am from your hotel. You move towards the north of Siena and after a beautiful road along the local interstate SR222 you arrive at Montemaggio Winery by 10 am. With this experience you will have a visit of the vineyards with explanation of working process and of organic agriculture, walking through the gardens of the villa and view of the vegetable garden you will arrive to the cellar with explanation of winemaking process. After that you will taste seven wines and the Grappa, with local products After this experience, on your way back to Siena you will stop at 11.30 pm at La Lastra Winery, where Renato or his wife will let you have a special unch experience with a combination of their wines (Vernaccia di San Gimignano is their highlight according to us!) in a very familiar atmosphere and then you'll visit the winery and the vineyard together with the wine maker or a member of the family.

Meet your driver-guide head south to Val d’Orcia, a corner of beautiful and untouched Tuscan countryside dotted with picturesque villages. After picking you up from your hotel, the driver will take you to some of the most beautiful villages of Val d’Orcia, such as Pienza, a beautiful town known as the "Ideal City” because it is one of the first examples of humanistic ideal urban planning, and Montalcino, a walled medieval town famous for the production of the renowned Brunello wine. Other iconic sights of Val d’Orcia include the Romanesque Abbey of Sant' Antimo, and the village of San Quirico d’Orcia, whose surroundings are home to the idyllic Vitaleta chapel and the charming hamlet of Bagno Vignoni, whose main square is entirely occupied by a huge thermal bath from ancient Roman times.