Top Siena Adventure Tours

Get views you can't find anywhere else on this hot-air balloon ride over Tuscany. Starting in Siena, float above the countryside and take in scenic views of the low-rolling hills, some clad in grape vines, others crowned by a rustic ancient villa. Ascend as high as 2,000 feet (609 meters) and enjoy seeing the countryside and surrounding ancient villages and towns. Upon landing, enjoy a glass of sparkling wine to celebrate your experience.

Become a pilgrim of sorts and take a scenic hike on the historic Via Francigena, an old pilgrimage route that stretched from Canterbury in England to Rome. The rural route takes you through villages, vineyards, and some of the most scenic countryside in Tuscany. Best of all, once you get to the medieval village of Monteriggioni you're rewarded with a wine tasting. At the end, head back to Siena via train.

Explore the landscape of Tuscany on a private, full-day cycling tour from Siena. With the full attention of your guide, follow a route along the Via Francigena, an ancient pilgrimage route that once linked Canterbury to Rome and a popular destination for photographers. Rest and refuel after a day of activity with a three-course lunch and wine pairings at a Tuscan vineyard. Hotel pickup and drop-off is included.

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.

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.

The Tuscan countryside is a premier hiking destination, but navigating unfamiliar trails and country roads on your own can be daunting. On this private hiking tour, explore the rolling hills and vineyards stress-free with a guide leading the way. Meet in Siena and transfer to the trailhead by minivan, setting off through the verdant countryside and past rustic villages. Take a break to relax over a classic lunch of Tuscan treats and then travel via minivan to San Gimignano for a stroll through town and along a stretch of the Via Francigena before the return ride to Siena.

Avoid the hassle of planning routes between scattered wine towns and booking separate tastings on your own with a guided day trip from Siena. This experience connects the flavors of Montepulciano and Pienza with the scenic landscapes of Val d'Orcia, letting you move easily between villages without logistics stress. Spend your time enjoying wine, local food, and countryside views at a relaxed pace.

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.

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 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.

Spend your day through the picturesque Tuscan landscape on an original Vespa scooter, enjoying peaceful roads that wind through the rolling hills of Chianti. This unique experience allows you to immerse yourself fully in the sights, scents, and sounds of the Tuscan countryside. As you navigate the winding roads, take in panoramic views of vineyards, olive groves, and ancient farmhouses dotting the landscape. Midway through your excursion, make a stop at a renowned winery nestled in the heart of the Chianti region. Here, indulge in a delightful wine tasting experience, savoring the flavors of locally produced wines that have been crafted with passion and expertise. After replenishing your energy, discover hidden gems off the beaten path, uncovering the rich history and culture that define this beloved region.

Join a journey through the breathtaking hills of Chianti aboard our state-of-the-art and high-speed ATVs. Pass through scenic trails amidst the iconic landscapes of Tuscany, enveloped by fields of shimmering gold and verdant vineyards, immersing yourself in the unrivaled beauty of nature. Experience the excitement of riding our quadricycles firsthand as you explore the Chianti Area under the expert guidance of our seasoned escorts. Feel the adrenaline surge as you discover hidden treasures and marvel at the stunning vistas along the best routes. Join an exclusive winery experience with panoramic views, savoring every sip while absorbing the tranquility of your surroundings. After this journey, return to the starting point where your ATV adventure began, ready to share your unforgettable experience with friends and relive the magic of Chianti's enchanting landscapes.

Join this adventure through the picturesque countryside of Tuscany aboard our ultra-modern Polar 6-seater quad, expertly driven by our skilled guide. Immerse yourself in the natural beauty of Tuscany and indulge in a wine tasting in a winery. Experience the perfect blend of adrenaline and nature, creating unforgettable memories of Tuscany to cherish and share with your loved ones. Discover hidden corners of the countryside inaccessible by other means of transportation, from ancient farmhouses to medieval castles, charming hamlets, and breathtaking vistas. Spot wildlife such as boar, deer, foxes, hares, and pheasants as you venture through this untamed landscape. Traverse winding paths amidst vineyards and crystal-clear streams teeming with fish, soaking in the tranquility of nature.

Experience the delight of cruising through the Tuscan countryside aboard an original Piaggio Ape Calessino. Revel in the unique charm of Chianti's landscapes as you wind along peaceful roads, surrounded by the fragrant scents of the countryside and the gentle hum of farm life. Join our daily tour and immerse yourself in the heart of Tuscany's medieval villages, guided by our knowledgeable escorts. Pass through the Chianti hills, taking in the picturesque scenery at every turn. Your journey will culminate in a visit to a renowned winery, where you'll indulge in a wine tasting and a delightful light lunch.

Experience the enchanting Tuscan countryside as if you've stepped into an old Italian movie, cruising in a vintage FIAT 500 across the rolling hills of Chianti. Let us transform this dream into reality for you on our scenic driving tour along the most captivating routes and stops at the most charming villages. These hidden gems offer a glimpse into the authentic essence of Tuscany, preserving their timeless beauty for centuries. Immerse yourself in the sights and sounds of the region as you drive through winding roads, bordered by vineyards and olive groves. Marvel at medieval village, each one a testament to Tuscany's rich history and culture. During your journey, take a break to join a wine tasting at a Chianti winery. Savor the flavors of the region as you sip on locally produced wines, surrounded by breathtaking scenery that seems straight out of a painting.

Immerse yourself in the Tuscan countryside on a small-group ATV excursion.  Select a start time that works for you and get a briefing from your guide. Test out the ATV until you feel comfortable. Then, enjoy the adrenaline rush as you discover the UNESCO-listed Crete Senesi area from Chianti to Val d’Orcia by ATV. Your guide is on hand at all times to offer assistance or answer questions.

Fly the sweet hills and vineyards of Tuscany with a hot air balloon flight through the Val d'Orcia. Discover the magic of flight through the energy of the wind and fire. Get at an altitude of about 2000 feet and beyond, every day nature leads us to discover new landscapes. Surprising your family with a fantastic and unique tour.

Take a break from the crowds in Siena, and spend an afternoon in the wine town of Montalcino on this group tour. Don't worry about hiring a car to get there, with transportation all sorted. Learn about Brunello di Montalcino wine and its production, along with wine tastings paired with local snacks. Admire views of the Tuscan countryside from this hill town as you discover the region’s generations-old winemaking traditions.

Experience the culinary delights of the Chianti region on a half-day tour from Florence to a Tuscan farmhouse. Go in search of truffles with an expert guide and his trained dog during a 1-hour forest walk, then enjoy a traditional lunch that features the fresh truffles accompanied by extra virgin olive oil and Chianti Classico wine. Includes tastings of wine, olive oil, and honey, and a 3-course lunch.