Top Siena Tours, Sightseeing & Cruises

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.

There are many ways to spend an evening in Tuscany, but few allow you to experience it from the inside. Just a few minutes from Siena, between Chianti and the Crete Senesi, this experience takes you through vineyards, cellars, and history, guided directly by the people who produce the wine every day. What makes it special is the combination of a visit to a family-run winery, a tasting of our wines, and a traditional Tuscan dinner served at sunset on a panoramic terrace overlooking two of the most fascinating landscapes in the Siena area. It is not just a wine tasting or a dinner, but an authentic experience where wine, territory, tradition, and hospitality come together in a relaxed and genuine atmosphere.

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.

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.

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.

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.

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 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.

Just a few minutes from Siena, San Giorgio a Lapi offers an authentic experience in the heart of Tuscany, in a unique location between Chianti Classico and Chianti Colli Senesi. What makes this tour special is the opportunity to experience a family-run winery firsthand, guided by the people who cultivate the vineyards and produce the wine. In addition to visiting the vineyards and wine cellars, you will discover the 11th-century Church of San Giorgio a Lapi and conclude your experience on our panoramic terrace overlooking the hills of Chianti and the Crete Senesi, where you will enjoy a guided tasting of 4 wines and a traditional Tuscan lunch prepared with local ingredients. A journey that combines wine, history, landscape, and genuine Tuscan hospitality.

Siena is one of Tuscany's most fascinating hill towns, but most visitors check off a handful of famous sights and move on. Get a more in-depth, personalized introduction to this medieval city on this private walking tour, fully customized to your pace and interests. Focus on the historic architecture, traditional Palio festival, or local food scene, or combine culture and cuisine to create a unique itinerary. Choose an express tour of just a few hours or a full-day deep dive that takes you to little-known gems most tourists miss.

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.

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.

Journey into Italy's opera culture during your time in Siena on this night out. Opera singers perform classic pieces from works like La Traviata, La Bohème, and Madame Butterfly. Whether you're an opera lover or would like to experience something new in the charming town of Siena, this night out is a great opportunity to witness Italian arts and culture.

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.

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.

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.

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.

We were born here in Tuscany, we rent our e-bikes at discounted prices. We will provide you with all the information about our places and the best itineraries, both for beginners and for the more experienced. Cycling in our countryside is something unique. Like in a movie ....

Take a break from sightseeing and head to the Tuscan countryside surrounding Siena to join a local forager on a truffle hunt through the woods. Follow your host and his pups across the hills as they search out precious tubers and learn all there is to know about truffles and the dogs trained to hunt them. Afterwards, head back to Siena to sample a number of truffle products in a local gourmet shop.

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?

Indulge in Siena's culinary treasures on a private tour designed to delight your palate, led by an expert local guide. Stroll through charming cobblestone streets, where the enticing aromas from bustling food stalls beckon. Begin your epicurean journey with the crispy perfection of coccoli, drizzled with aromatic olive oil, and savor the multi-layered flavors of savory panini, each bite a testament to Siena's rich gastronomic heritage. As you meander through the city, your guide will share enthralling tales of Siena's history, blending tradition with modern culinary innovations. Discover how the city's vibrant food scene reflects its cultural tapestry, making this tour an ideal exploration for devoted foodies and curious travelers alike. Each stop unveils a new chapter in Siena's epicurean story, promising a memorable adventure that intertwines taste and tradition in the heart of this historic city.

Experience the enchantment of Siena with an enthusiastic local guide on this private tour. Discover famous sites such as Duomo di Siena, Piccolomini Library, and Piazza del Campo, while revealing secret treasures on your journey. This personalized, adjustable tour allows you to explore Siena in your style, featuring expert suggestions and captivating narratives that animate the city’s history.

Taste your way through the most delicious private food tour of Siena as you immerse yourself in Tuscan culinary culture with a knowledgeable local host. Indulge in six or 10 iconic treats, including pastries, espresso, and savory bites, while exploring favorite local spots and must-see landmarks like Piazza del Campo and Torre del Mangia. Along the way, discover the rich flavors and history that make Siena unforgettable.

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.