Top Siena Tours, Sightseeing & Cruises

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.

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 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.

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.

When you’re in the Tuscan city of Siena, don’t miss the chance to discover its famous wines and enjoy some local food, too. This small-group wine tour visits a winery near Siena’s historical center, and gives the lowdown on the winery’s organic production methods. After visiting the vineyard, you’ll savor a meal made with local produce along with samples of five organic wine varietals. Numbers are limited to 12 per group.

Discover with me the unknown and most fascinating Siena with this unique and unusual tour. SECRET SIENA WALKING TOUR, is my favorite to discover history, art and architecture of this wonderful medieval town,away from the crowded tourist routes. Uncover hidden squares, medieval alleys, 14° century perfectly preserved palaces, courtyards and ancient fountains with bewitching legends Enjoy the breathtaking views of Siena, perfect for unforgettable photos and peaceful and suggestive corners. Learn the stories about ancient noble families, medieval pilgrims and ancient disappeared monasteries Explore the territory of a Contrada to know the history of Palio race and visit, if you like, its private museum that I can book for you( tickets not included).

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.

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.

This walking tour offers a truly local take on Siena, far beyond the postcard views. With your host, you’ll explore hidden chapels, medieval backstreets, peaceful gardens, and the living traditions of the Palio and contrade. Whether you're tracing the path of a district rivalry, admiring Gothic architecture, or sipping wine in a tucked-away enoteca, this is your chance to explore like a local, not a tourist. After booking, you’ll receive a short questionnaire to share your interests and travel style. Based on your responses, you’ll be matched with a like-minded host who will contact you directly to suggest a personalized itinerary. You’ll agree on a meeting point and time, and your route can adapt throughout the day based on what captures your interest.

Open the doors of the Sienese countryside on horseback and immerse yourself in the breathtaking landscapes of the Tuscan countryside. Cross vineyards, rivers, olive groves and roads with cypress trees. See and touch the flora and fauna of the Sienese countryside with a guide who will explain the various plants and animals and the history of the places you will encounter during the tour. The walks in the Sienese countryside are suitable for everyone, from beginners to experts. The horses used for the tours are well trained and calm, suitable for everyone. Stop for a picnic in the shade of the river in the Siena area or for a tour and tasting in a winery. Spend an unforgettable day and discover Tuscany with different eyes as you ride your horse, seeing and touching the historic countryside and traditions of Siena.

Siena is one of Italy’s most captivating medieval cityscapes, but its mazelike historic center is a challenge to navigate. With this private tour, explore with a local guide to cover the highlights in a few hours. Marvel at the Piazza del Campo, stroll the historic center, and take in the Basilica of St. Francis and Medici Fortress while you learn about the local history and architecture.

Discover the best of Siena’s traditional cuisine and food scene with the insights of a local insider guide on this small-group food tour. Set off with your foodie guide and group of just 12 fellow gourmands to visit the top artisan food shops, market stands, and other landmark eateries to sample a range of savory and sweet delicacies. Feast on charcuterie boards, pici pasta, ricciarelli cookies, and more as you explore the old town.

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.

Take your Tuscan wine tasting to the next level with this one-of-a-kind experience set in an authentic medieval aqueduct hidden below the historic city center. Settle in among brick vaults and tunnels dug directly into the stone to sip a selection of Brunello di Montalcino and Super Tuscan wines from the vineyards of Siena and Chianti, paired with local cheese.

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.

Commence your journey at the iconic Piazza del Campo, immersing yourself in the vibrant atmosphere of Siena's renowned square. Delve into the city's history at Palazzo Pubblico, an architectural marvel serving as the seat of governance. Meander through historic streets, passing Palazzo Tolomei and Palazzo Salimbeni, both UNESCO-listed treasures. Continue to the Basilica of San Domenico, housing the relics of Saint Catherine, before a visit to the Sanctuary of St. Catherine of Siena. Admire the Baptistery and opt for a guided tour of the awe-inspiring Siena Cathedral, adorned with masterpieces of Italian artistry.

DEPARTURE GUARANTEED! Enjoy a perfect day trip visiting 3 of the most impressive places in Tuscany. Montalcino, house of "Brunello" wine; Pienza, well known for the "Pecorino" cheese and Montepulciano where the undisputed symbol is the "Nobile di Montepulciano" wine! Please note that from November to April I cannot guarantee the restaurant with view, as stated in the inclusions. The Valdorcia has been recognized as UNESCO world heritage site since 2004, as it was an inspiration for many Renaissance painters. There you will be surrounded by impressive views, art, culture, amazing wine and delicious food! Your semi private tour will be on board of a premium minivan with an English speaking driver, air conditioning and free water. WHY CHOOSE ME? Secure bookings, Guaranted Departures! 48 hours Cancellation policy, best rates guaranteed! Group of maximum 8 people.

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.

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.

If you're looking for a fun and curious way to visit Siena, you've come to the right place! With this digital guide created with the support of a local, you will be able to visit all the most important monuments at your own pace: Piazza del Campo, the Duomo, Basilica di San Domenico and much more! You'll get to know the stories and curiosities of Siena! But also you will discover everything about local foods, Italian aperitivo in authentic local restaurants, and much more! What are you waiting for?

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.

To fully discover a city one may participate in a lot of tours and go eat at many venues published on travel guides and recommended by online travellers but the true local knows where to take you and you'll be paired with a Local Expert who will tell you stories, curiosities and will take you to spots outside of the tourist lens. We'll visit the most important and the least acknowledged hitspots of the Medieval Centre of Siena. Also, with us, you'll be able to eat some of the most typical snacks available in the city and taste the local Tuscan Wines, which mean a lot to the gastronomic history of the locals. The activity is suitable to people of all ages, from the kid discovering the curiosities behing the walls of the centre to the adults learning about Siena's culture.

The Best Way to Discover Siena: Scavenger Hunt & Self-Guided Tour. Play, learn, and walk! Explore at your own pace with a 100% self-guided activity. Start anytime (24/7) with no guides or schedules. Pause for a traditional Ricciarelli almond cookie in a local pastry shop or enjoy the medieval atmosphere of the Piazza del Campo and resume whenever you're ready—even the next day. This unique team-building activity is perfect for couples, families, and groups. The "Complete City" Package Everything you need in one app: Interactive Game: Solve puzzles and discover 10+ major attractions, plus hidden gems revealed along the way. Cultural Context: Read the history and legends of each site as you explore. Insider Tips: Access hand-picked local restaurant and shop recommendations. What you will visit: Pinacoteca Nazionale, Baptistery of St John, Palazzo Piccolomini, Loggia del Papa, Tower of Mangia, Pubblico Palace, Fonte Gaia, Santa Maria della Scala, Facciatone, and the Duomo di Siena.