Top Siena Private and Luxury

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.

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.

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.

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 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.

Discover the authentic beauty of Tuscany with our tour of vineyards, art and flavors. We start with a walk through the vineyards, immersed in the heart of Chianti, to reach the picturesque church of San Giorgio a Lapi, dating back to 1100. Here you can admire three splendid frescoes by Nasini, a true hidden jewel. After the visit, we will enter our cellars to discover the winemaking and aging process of the wine. And to top it off, a tasting is waiting for you on our panoramic terrace, overlooking the Crete Senesi, accompanied by a lunch with the best typical Tuscan products, all in the shade of an ancient white mulberry tree. Live an unforgettable experience between nature, history and good wine!

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 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.

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. Please note that from November to April, and in case of bad weather, lunch will take place indoors. For tours departing on Mondays, lunch is always served in an indoor restaurant. 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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

Siena is one of the most intact medieval towns in Italy, rich in art and architecture. Visit its highlights in just a few hours with this walking tour through the old town. Follow your guide to admire the Duomo and Piazza del Campo, marvel at the Churches of St. Dominic and St. Catherine of Siena, and wander through the historic warren of narrow lanes and quiet squares.

The hot air balloon tour is a magical experience, a true adventure carried out in total safety by flight professionals. Our pilots, all with great experience, are ENAC certified commercial pilots. They will guide you during your trip, sharing with you detailed information about hot air balloons and satisfying all your curiosities about the flight and its navigation. Don't wait any longer, immerse yourself in this extraordinary adventure.

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.

Brunello di Montalcino is one of Italy's most prestigious wines, but navigating to the rural wineries outside of Montalcino on your own can be stressful. On this private wine tour, let your driver take the wheel and focus on vineyard views as you make your way to the top wine estates and cellars for exclusive tasting experiences. Explore stunning vineyards, learn about traditional winemaking techniques, and savor the rich flavors of Tuscany with guided tastings and a traditional lunch.