Top Siena Private Sightseeing Tours

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.

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.

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.

Discover UNESCO-listed Siena through the eyes of a local on this custom-made Lokafy walking tour. Skip the typical guided tour and instead connect with a Siena local who will show you around their city like a friend and introduce you to the neighborhoods that they know and love. As you explore the city, gain an insight into Tuscan culture, cuisine, and everyday life; and receive recommendations on where to eat, drink, and shop.

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.

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.

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.

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.

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.

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.

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.

Travel off-road through the Chianti valley on this day-long Tuscan wine tour. As your guide drives a vintage SUV, you'll gaze out at the gentle green hills and grapevine groves that typify the landscape. Stop at a few wineries to sample several varietals of wine along with local products such as honey and olive oil, then relax over a traditional Tuscan picnic for lunch at your final stop.

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 vehicle with a private guide who shares the best of the region.

Pienza and Montalcino are top foodie destinations, but getting there by train and bus can eat hours out of your day. Experience the area's top cheese and wine with ease on this private tour from Siena. Admire the Val d’Orcia scenery, learn about cheese making during an organic dairy farm tour, visit the World Heritage–listed town of Pienza, and enjoy tastings of the region’s renowned Brunello wine at a Montalcino winery.

Opt for a personalized experience of Siena’s top attraction on a private tour of Siena Cathedral. With just your private guide and party, discover easy-to-miss details in the cathedral’s interior and benefit from commentary integral to understanding the statues of Michelangelo and the art inside the Chapel of St. John the Baptist. Plus, booking in advance means you save hours of waiting in line with a skip-the-line admission 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.

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.

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.

Two magic hours to discover the city with Your children! Children and adults will learn the city's history having fun and being enriched by anecdotes and legends from the Middle Ages! Magic is hiding in plain sight.... Stroll around the streets of Siena to discover the mysteries, reach the ancient castle and discover the symbol of Siena, the she-wolf, which from the top of its columns protects us. Learn about the 17 districts that we call Contrade and find the animals that represent them. The Contrade participate to the horse race twice a year, an incredible event! Have fun to watch the videos, find the stables where the horses sleep for four days and the little fountains hidden through the streets where the Sienese are baptized.

Avoid the challenge of navigating Tuscany’s rural roads and finding hidden countryside trails on your own with a guided horseback ride from Siena. This gentle journey carries you through rolling hills, vineyards, and olive groves, reaching quiet landscapes that cars can’t access. Ride at a relaxed pace while taking in the region’s natural beauty and rural charm without any planning or navigation stress.

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.

Experience the Tuscan countryside from a perspective rare to visitors on a private Vespa tour from Siena. In addition to navigating for you, your guide ensures the best views and stops for photo opportunities along the way. The day includes a Tuscan–style lunch and complimentary wine tasting with vineyard views.

Siena has one of the most intact medieval cityscapes in Italy, and with this walking tour, you can take in the hill town’s top sights in just two hours. Skip the hassle of following a map and instead head straight to the highlights with a guide. Stroll past Piazza del Campo, the town hall, and the Basilica of San Domenico, plus stop in the cathedral to marvel at works by Donatello and Bernini.