Top Siena Sporting Events

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.

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.

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.

This experience stands out by combining an indulgent cooking class on a panoramic terrace kitchen with a tour of vineyards and a 13th-century castle that's been in the family for 17 generations. Learn to make classic Tuscan dishes such as tagliatelle with Tuscan sauces and braised beef, and pair each with local wines for lunch. Then, tour the castle and wine cellar.

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.

This quad tour is much more than just a ride – it’s a journey into the most authentic side of Tuscany, following scenic dirt and country roads far from mass tourism, with breathtaking views around every corner. In 4 hours, you’ll experience the perfect blend of adventure, culture, and nature, discovering iconic spots such as the Sentiero del Nobile, San Biagio Temple, Madonna della Querce, and the famous zig-zag cypress road. You’ll explore hidden gems you wouldn’t find on your own, including Gladiator movie locations, the legendary Quercia delle Checch, and peaceful woodland trails. With your expert guide, every kilometer will be safe, exciting, and full of local stories. The perfect experience for travelers who want to live the real Tuscany, filled with thrill and beauty.

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.

Inject a bit of adventure into your wine tasting experience with this ATV tour through the vineyard-covered countryside surrounding Siena. Take in views of the UNESCO-listed Crete Senesi landscape as you zip over the hills behind your guide, following unpaved trails through woods and fields. End at a family-run cellar to sample Tuscan wines paired with local gourmet specialties and snacks.

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.

Enjoy a private tour of two of Montalcino’s most exclusive wineries, taste their award winning wines and visit their winemaking facilities. Our native English speaking guide will be with you throughout your unforgettable experience and will take you to lunch at one of the regions top restaurants.

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.

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.

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.

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.

Tour with a passionate Toscana lover, sommelier guide expert on Brunello. Discover Tuscany with local expert out of beaten path.