Top Siena Day Trips

Experience the highlights of southern Tuscany on a full-day tour from Siena through the rolling landscapes of the Val d’Orcia. Travel in comfort and enjoy a perfect blend of food, wine, history, and scenery. Your first stop is Montepulciano, where you’ll enjoy an authentic Tuscan lunch featuring local cured meats and cheeses, followed by handmade Pici pasta with ragù, or tomato sauce for vegetarian guests. During lunch, take part in a guided tasting of Rosso di Montepulciano and the renowned Nobile di Montepulciano, perfectly paired with the regional cuisine. Continue to Pienza, the “ideal Renaissance city,” and enjoy free time to stroll its picturesque streets, admire panoramic countryside views, and browse artisan food shops. In the afternoon, reach Montalcino, home of the prestigious Brunello di Montalcino. Visit a local winery for a guided tasting and learn about the traditions and aging process behind one of Italy’s most celebrated wines.

Discover Tuscany's stunning landscape, culinary delights, and UNESCO-listed sites on a day trip to Montepulciano and Pienza from Siena. Avoid the hassle of driving yourself and be 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 a visit to a winery.

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.

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.

Tuscany is world-renowned for its wine, so ensure you get an insider’s glimpse into the industry during a tasting tour of the vineyards surrounding Siena. Receive personalized attention in a small group as you visit a historical cellar and educate your palate to recognize subtle flavors with the help of a sommelier.

Explore the enchanting Chianti wine region on a half-day tour from Siena, where rolling hills and lush vineyards create an idyllic backdrop. Visit Castellina in Chianti and enjoy exclusive wine tastings at renowned estates. This tour is tailored for wine lovers and nature enthusiasts, offering a rich cultural experience through Tuscany's famous landscapes. With expert multilingual guides, savor the essence of Chianti’s rich heritage and take in the stunning scenery that has inspired countless artists and wine aficionados.

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.

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.

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.

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.

Spend a memorable day exploring Tuscany’s most famous landmarks and landscapes on a relaxed and well-balanced itinerary from Siena. Your journey begins with a comfortable transfer by air-conditioned coach through the rolling hills of the Tuscan countryside. Reach Pisa, where you will have free time to explore the stunning Piazza dei Miracoli, a UNESCO World Heritage Site. Admire the world-famous Leaning Tower, the Cathedral, and the Baptistery from the outside, and take your time capturing unforgettable photos. Continue your experience with a stop in the heart of Chianti, where you will enjoy a traditional Tuscan lunch paired with a guided wine tasting at a local winery. In the afternoon, arrive in San Gimignano, one of Tuscany’s best-preserved medieval towns. On the way back from Pisa, you’ll pass through Florence before returning to Siena. This allows for a smooth and well-organized route across Tuscany.

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.

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.

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.

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 the top sights in Siena without the hassle of a guidebook or map with this small-group walking tour through the medieval old town. Join your local guide for a stroll along picturesque historic lanes to take in landmarks like the Piazza del Campo, Basilica of San Domenico, and Sanctuary of St. Catherine of Siena. Opt to add on a visit to the city’s magnificent Cathedral, rich in artworks by Renaissance masters.

Discover the picturesque wine region of Chianti on a half-day excursion from Siena. Enjoy the Tuscan scenery of gently undulating hills and vineyards while tasting Chianti wines. A day journey from Siena to the Chianti region allows you to experience the gorgeous Tuscan landscape. Begin with a visit to Castellina in Chianti, followed by a wine tasting at a nearby vineyard. Immerse yourself in the bright colors of the rolling hills, where the views, smells, and flavors of the region will captivate your senses. Enjoy a stroll in Monteriggioni, a medieval village where time seems to stop. Proceed to another winery in the heart of the Chianti Classico region, where you can have a second wine tasting and sample extra virgin olive oil. A return trip to Siena marks the end of the excursion.

Learn to cook traditional Italian dishes during this Tuscan cooking class in Siena. From homemade pastas to juicy cuts of meat, a professional chef leads you through a combination of family-favorite recipes and time-tested dishes, culminating with a shared meal and excellent wine. This class is held in a professional kitchen and limited to a small group of 15 people or fewer for a more intimate experience.

Skip the dry guidebook and hassle of following a map and discover the medieval streets of Siena with a personal guide at your side who knows how to bring its history to life. Take in the top sights plus find hidden-away corners far from the tourist crowds, learn history and lore that most tourists miss, and create a personalized itinerary that suits your pace and interests.

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, get familiar with your bike and helmet, and head into the Chianti Hills. With just a small group for company, set off on a tour of the countryside, visit a restored monastery, and head to a local farm/winery, where you can enjoy a traditional meal and generous wine tasting.

Splendid Classic Siena Tour with guaranteed departure from Via di Città at 11am in English and at 12.15pm in Italian. An expert local Guide will introduce you, in an interesting and pleasant way, to the history of Siena, the Duomo, Piazza del Campo and other monuments of the city. We will talk about the Palio, the districts and visit the lesser known and quieter corners of the city. Including entrance ticket to the Duomo. In case of religious celebrations or extraordinary closures (such as Sunday morning for Mass), the visit will be moved to the Antico Ospedale di Santa Maria della Scala, still guaranteeing a complete experience.

This is an exclusive tour for you and your loved ones and, comfortably seated in the car you can enjoy the beauty of the places. In fact, we will see fascinating landscapes that are a little lost in time. In fact, the Maremma, in addition to being considered the new Eldorado for its powerful and elegant wines, offers wild and splendid landscapes. The typical local cuisine is Mediterranean. The people of Maremma are the most outspoken in Italy. Furthermore, the story I told will take us back in time to the Etruscans. As our ancestral ancestors did, you can, if you wish, take a thermal bath in the Saturnia waterfalls. New shower and toilet rooms available.