Top Siena Day Trips - page 3

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.

Discover the medieval charm of Monteriggioni on a private luxury e-bike experience, ride scenic Tuscan roads, enjoy a curated lunch paired with fine wines, and end with an exclusive winery visit scheduled just for your group. More than a bike tour, this is a curated Tuscan experience for couples, families, and small groups seeking an authentic, relaxed, and elevated way to explore. Led by a professional local cycling guide, far from crowded routes, your ride is tailored to your pace, allowing you to fully enjoy the landscape and timeless atmosphere. Premium e-bikes ensure a smooth, accessible ride with minimal effort. The experience concludes with a refined lunch and wine pairing in a carefully selected winery, featuring a private dining room reserved for you and a private cellar visit without overlapping guests. A seamless Tuscan day blending cycling, culture, landscape, and fine wine — designed for comfort, privacy, and authenticity.

E-bike tour that takes you through the fascinating hills of the Chianti, crossing the iconic gravel roads of the Eroica, revealing, in a slow and contemplative way, an area rich in food and wine traditions, cradle of the famous Chianti Classico wine and proud of its tradition and culture linked to the long rivalry between Siena and Florence. In addition to it, this tour has an Arts footprint. We'll lead you through some hidden sculptures, located throughout the landscape, as a warm up to our stop at the Chianti Sculpture Park, where you'll visit some contemporary sculptures and installations. We'll build on to the arts experience by stopping at the hamlet of Scopeto, where the film "Letters to Juliet" has been shot. Least, but not last, it will be wine time right after at the Scopeto Winery, where you can further develop your reconnaissance of the territory by tasting one of its maximum expression: the Chianti Classico. We then, climb back to our comfortable ebikes to return to Siena

On this wine-tasting tour, you will sample some of the region’s best prosecco, rosé, and a variety of Tuscan red wines. Every glass is perfectly paired with local cured meats, cheeses, and various homemade pasta dishes (please inform us if you have any dietary restrictions). As you make your way through the villa’s multiple tasting rooms, you will discover that the Corbucci Wine Boutique not only produces excellent wine, they also make several other exceptional products, including limoncello, grappa, olive oil, and balsamic vinegar. All products are made from the finest, local ingredients and crafted with expert care. All good things must come to an end, and so must this tour. But there is no better way to conclude a wine-tasting experience than with a little more wine. To finish what promises to be an already wonderful experience, your gracious hosts will invite you to join them in raising a glass of Vin Santo—a traditional Tuscan dessert wine—to send you off with a sweet goodbye.

If you’re staying in Siena but still want a deep dive into one of Florence’s top attractions, this tour of Florence Duomo (Cattedrale di Santa Maria del Fiore) is made for you. Round-trip train tickets are included, so you don’t have to navigate booking websites in another language, while a guided tour of the cathedral helps you learn much more than you would alone.

This private tour is designed to offer an authentic experience with maximum comfort and local insight. It starts directly from your hotel in a fully licensed Mercedes van with air conditioning for a smooth and relaxing ride. Accompanied by a professional driver-guide-certified sommelier, fluent in English and Italian born and raised in the Montalcino area. Travel through the stunning Val d’Orcia admired worldwide for its rolling hills and iconic landscapes. The highlight of the tour is an exclusive visit to a family-owned, organic Brunello winery, where you will walk through the vineyards, tour the cellars, and enjoy a guided tasting of selected red wines, including the celebrated Brunello di Montalcino, accompanied by a tasting extra virgin olive oil. The experience concludes with free time in the medieval town of Montalcino, the heart of the Brunello wine region, where you can explore historic streets, admire monuments, and browse charming local shops at your own pace.

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.

Fiat 500 represents the emblem of Italian Style. Shape, size and its unique charm make of this car a special and authentic symbol beyond it’s simple use as a vehicle. Ideal both on city’s tiny alleys and on the famous country-side windy roads. We will be visiting typical medieval villages, get in touch with local wine and food producers as well as artisans, and stop along the way to take some picturesque photos that will become indelible memories. An experienced tour guide will lead you around and show you the way as only a local can. The tour ends in a local farm where we will be hosted by a family that has been living there since centuries, producing their own wine, Chianti Classico. We will have the chance to visit the property including the cellar and then relax where a traditional Tuscan lunch will be served, all accompanied by their wines. Pick up and drop off from your accomodation in Siena included.

Surround yourself with the unrivaled scenery of Valle de Orcia while trying some of its epicurean delights on a private tour from Siena. Begin in the hill town of Montalcino, where you'll sip on locally produced wine at a popular winery. Later, head to the historic center of UNESCO-listed Pienza, where you'll enjoy free time to explore independently. A typical Tuscan lunch, cheese tasting, and hotel pickup are included.

Hop on a full-day private tour to Florence and San Gimignano from Siena. Your adventure kicks off with a drive from Siena to Florence to explore the city center. Take a guided walking tour of the historic center and see key landmarks, including the Duomo, the Uffizi Gallery, and the Ponte Vecchio. Then, it's off to experience the medieval town of San Gimignano, known as the "medieval Manhattan."

Your Professional English-speaking Driver will pick you up from your accommodation in Siena. All you have to do is get in and relax. Enjoy a 3-hour one-way Private Transfer in a comfortable, fully air-conditioned comfortable vehicle to Fiumicino Fco International Airport. Pit stop half-way to relax. Viceversa trip available according selected option. Upgradable option to visit the old town of Orvieto for an extra 3 hours. Worry-Free and Safe Private Tour Experience, operated only with: • Expert Professional English-Speaking Drivers • Welcoming by private licensed fully-insured air-conditioned comfortable Vehicles

In the heart of Tuscany and Chianti. Hills, vineyards, unspoiled nature. Intact medieval cities. Unforgettable atmospheres.