Siena is a treasure trove of charm, history, and stunning landscapes, making it an ideal base for full-day tours that go beyond the city walls. Whether you’re a wine enthusiast, a history lover, or someone eager to explore picturesque hill towns, Siena offers options that cater to all interests. Among our favorites is the Full-Day 2 Wineries Tour in Montepulciano with Tasting and Lunch — a seamless way to experience Tuscany’s renowned wines without the hassle of driving. This tour combines visits to local wineries with a delicious traditional lunch in Montepulciano, providing an authentic taste of the region. We also appreciate the PRIVATE TOUR of Volterra & San Gimignano with Wine Tasting, which offers flexibility and a chance to explore two of Tuscany’s most captivating hill towns comfortably. For those seeking a more active experience, the Full-Day Chianti Tour by Vespa Scooter from San Gimignano combines scenic riding and wine tasting for a memorable day of adventure.
Below, you’ll find a detailed look at each of these tours, highlighting what makes them stand out, their logistical details, and who they’re best suited for. Whether you want a laid-back day sampling wine, an independent exploration of historic towns, or an energetic Vespa ride through iconic landscapes, there’s something here for every traveler.
1. Full-Day 2 Wineries Tour in Montepulciano with Tasting and Lunch
At number 1 on our list, the Full-Day 2 Wineries Tour in Montepulciano with Tasting and Lunch offers a full immersion in Tuscany’s wine scene — perfect for those who want to taste regional specialties like Brunello and explore Montepulciano’s Renaissance streets. This 8-hour small-group tour departs from Siena, with hotel pickup and drop-off included, making it effortless to enjoy the day without worrying about driving. You’ll visit two local wineries where expert guides explain how these world-famous wines are made, followed by tastings that include regional delicacies such as Pecorino cheese.
What makes this tour stand out is the combination of wine, food, and scenery. The stops include a visit to a Nobile di Montepulciano producer for Brunello tasting, a walk through Montepulciano’s medieval core, and a scenic view of the Val d’Orcia, a UNESCO World Heritage site. The highlight is a three- or four-course lunch at a boutique winery, where local specialties are paired with different wines, creating a full sensory experience.
Guests consistently praise the professionalism of the driver and the quality of the wineries, with reviews highlighting the delicious wine, beautiful scenery, and knowledgeable guides. For around $382 per person, the value is excellent considering the personalized service and authentic experiences.
Bottom Line: This tour is ideal for wine lovers who want a well-rounded, hassle-free day tasting some of Tuscany’s best wines while enjoying Montepulciano’s historic charm.
2. PRIVATE TOUR: Full-Day Volterra & San Gimignano with Wine Tasting Experience
The Private Tour of Volterra & San Gimignano with Wine Tasting is perfect if you prefer a relaxed pace and personalized attention. For about $289 per person, this 7-hour experience offers hassle-free transportation and the freedom to explore without the constraints of a larger group. The day begins with a scenic drive through Tuscany’s rolling hills, passing olive groves and sunflower fields, setting the perfect backdrop.
You’ll enjoy self-guided visits to Volterra and San Gimignano, two hill towns packed with history and stunning architecture. In Volterra, you’ll see highlights like the Roman Theater, the Etruscan Arch, and the Palazzo dei Priori at your own pace. The town’s captivating medieval streets are ideal for wandering. Later, you’ll head to a family-run organic farm in Chianti for a lunch paired with five wines, offering an authentic taste of Tuscany’s wine-making tradition.
Guests report the guide’s friendliness and the flexibility of the itinerary as key benefits. The private nature of this tour makes it ideal for couples, families, or small groups wanting to customize their day. The inclusion of a scenic drive, combined with the opportunity to explore two sought-after towns, offers excellent value for the price.
Bottom Line: Best suited for travelers who want control over their schedule, enjoy history and wine, and prefer a more intimate experience.
3. Full-Day Chianti Tour by Vespa Scooter from San Gimignano
For the adventurous spirits, the Full-Day Chianti Tour by Vespa Scooter from San Gimignano delivers a lively way to explore Tuscany’s scenic wine country. Priced at $168 per person, this 7.5-hour tour combines sightseeing, riding, and wine tasting into one memorable day. You can ride as a passenger or upgrade to drive your Vespa — a must-try experience for those comfortable on two wheels.
The trip kicks off by heading into the Chianti hills, passing through Radda in Chianti, and stopping at Casale dello Sparviero, a charming farmhouse with a cypress-lined avenue. Here, you’ll enjoy a wine tasting and photos of the surrounding vineyard landscape. Afterward, you’ll have time to explore the medieval village of Monteriggioni before returning to San Gimignano.
Guests appreciate the mix of scenic riding and relaxed stops, though note the review ratings suggest it’s best for those comfortable on Vespas or scooters. The tour offers a unique perspective of Tuscany’s rolling vineyard hills, and the included lunch pairs perfectly with the wines you taste along the way.
Bottom Line: Ideal for active travelers seeking a fun, outdoorsy way to see Tuscany’s countryside and enjoy wine, especially those already familiar with riding scooters.
How to Choose
When selecting your full-day tour in Siena, consider your budget, physical activity level, and interests. If you’re a dedicated wine lover craving an in-depth tasting experience, the Montepulciano wine tour (full details here) offers a balanced mix of education and tasting. For those who want flexibility and culture, the private Volterra & San Gimignano tour is unbeatable. If you’re looking for a fun, energetic day exploring by scooter, the Vespa Chianti tour combines adventure and sightseeing.
Practical considerations include timing—most tours work best from spring to fall when the weather is ideal for outdoor activities—and booking early, especially for private tours or popular wine experiences.
Final Thoughts
Siena’s full-day tours showcase the region’s best offerings: world-class wines, historic hill towns, and scenic landscapes. For a comprehensive experience, the wine-focused Montepulciano tour is hard to beat, especially for those eager to learn and taste without the hassle. Meanwhile, travelers craving a personalized touch will find the Volterra & San Gimignano private tour perfect. And for the adventurers, the Vespa ride through Chianti offers a lively way to see the countryside.
No matter your preference, Siena’s full-day options promise memorable experiences. Booking early is advisable, as these tours tend to fill up fast, especially during peak season. Whichever you choose, you’re in for a rewarding day exploring Tuscany’s sights, flavors, and scenic beauty.
