Top Siena Private and Luxury

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.

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.

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.

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.

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.

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?

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 medieval landmarks of Siena and learn about their significance on this private walking tour. During this half-day tour, walk with your guide to highlight attractions around Siena’s historical center, including the Piazza del Campo, Siena Cathedral, and the Basilica di San Domenico. There is a limit of eight travelers on the tour and admission fees to attractions are not included.

Discover the island of Iceland at your own pace with this guided tour. With a tour of more than 2 hours, you can explore Siena discovering monuments such as Piazza Tolomei, Via Citta or the Duomo of the city. This option without schedules or groups allows you to enjoy the city flexibly, including recommendations on gastronomy and family activities. Available in six languages, this experience is ideal for those looking for hassle-free personalized tourism. - 2h self-guided tour with + 12 points of interest - Access to information in 6 languages: Spanish, English, Portuguese, French, Italian and German Explore iconic attractions and receive food recommendations. - You can purchase tickets and tickets for the different spaces without leaving the app. - No groups or schedules, ideal for traveling at your own pace.

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 most authentic side of Tuscany through a journey that weaves together landscape, history, and taste. The experience begins among the vineyards, in the heart of Chianti, leading to the small church of San Giorgio a Lapi, dating back to the 12th century, home to three remarkable frescoes by Nasini — a quiet place, suspended in time. The visit then continues in the cellar, where our work takes shape: from vinification to aging, each step reflects a choice, an idea, a story. The experience then opens onto the panoramic terrace overlooking the Crete Senesi, under the shade of an ancient white mulberry tree, with a guided tasting of our wines accompanied by a full Tuscan meal: starter, first course, main course with side dish, and dessert. A moment to be lived slowly, among scents, light, and silence.

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.

Optimize your travel time with this private transfer that breaks up the trip from Siena to Rome with stops in Orvieto and Civita di Bagnoregio to sightsee, shop, and dine. Enjoy hassle-free pickup at your hotel or other accommodation in Siena and enjoy views of the Tuscan countryside as you head south. Stop for free time to explore Orvieto and Civita before drop-off at your final destination in Rome.

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.

Visit two of Tuscany's beautiful hilltop towns, plus enjoy tours and tastings at wineries in the Chianti hills and Montalcino on this small-group tour from Siena. All of your transport is included for a hassle-free experience, and there's even free time to explore Pienza on your own. Sample top Chianti and Brunello wine at two boutique wineries, and relax over a Tuscan lunch.

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.

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.

Shake up your sightseeing routine and skip the bland group tour with this app-based quest that leads you through Siena’s medieval center via engaging puzzles and challenges. Solve clues as you stroll through the old town at your own pace, learning about the city’s history and taking in landmark sights along the way. Delve into the power struggles between Siena’s ruling families in the Middle Ages and admire the squares, churches, and palaces they built.

There's no better way of immersing yourself in local culture than a cooking class. Get an authentic taste of northern Italy with this small-group cooking class in Siena. Led by a local chef, learn how to craft a delicious spread of Tuscan favorites plus a classic tiramisu. Afterward, enjoy the fruits of your labor as you savor your creations with your group and a glass of vino.

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.

Explore Chianti’s backroads and beautiful vistas while traveling in a private 4WD on this tour with hotel pickup. Soak up the scenery while a driver handles the country roads, stopping at off-the-beaten-track cellars and cantinas to taste several Chianti Classico wines along with Tuscan olive oil, honey, and other specialty products. Balance out all that wine with a traditional Tuscan lunch at a scenic family estate.

⭐ Experience Highlights — What’s Included Visit to Our Historic Wine Estate- Discover an organic winery with over 300 years of heritage. ️ Chef-Prepared Three-Course Lunch - Featuring the truffles you found with fresh caprese salad, pasta, dessert, or cheese selections Truffle & Wine Pairing- Guided tasting of three organic estate wines selected by our chef & Sommelier. Free Time to Explore the Vineyards - Enjoy breathtaking views overlooking Siena.