Siena is a fantastic base for full-day tours that go beyond the city walls. Its central location makes it easy to explore Tuscany’s most iconic sights—whether you’re after wine, medieval towns, or scenic countryside. What we particularly like about these tours is how they combine authentic experiences with convenient logistics. For example, the Full-Day 2 Wineries Tour in Montepulciano offers a relaxing way to sample Brunello and local delicacies without the hassle of driving yourself. Meanwhile, the private day trip takes you comfortably between hill towns with custom flexibility, which is perfect if you want a more personalized experience. Lastly, for those who want a bit of adventure, the Vespa tour from San Gimignano delivers a fun way to explore the rolling Chianti hills that you won’t forget.
Below, you’ll find an overview of each experience, highlighting what makes it unique and helping you choose the best fit.
1. Full-Day 2 Wineries Tour in Montepulciano with Tasting and Lunch
At number one on our list, this wine-focused tour is perfect for lovers of good vino and hearty Tuscan food. Over roughly eight hours, you’ll be picked up at your Siena hotel and taken to two local wineries where Brunello di Montalcino and Nobile di Montepulciano are the stars. The tour emphasizes a relaxed, small-group atmosphere—ideal for getting personalized insights.
What sets this experience apart is the chance to meet the people behind the wines and taste regional specialties during a 3/4-course lunch at an organic winery. The itinerary includes visits to the Renaissance jewel of Montepulciano, with its sweeping views of the Val d’Orcia and a recommended pecorino cheese tasting. Reviewers love the professionalism of the guide, Patrizio, and the quality of the wines and food. One guest says, “We had a great tour of two wineries and our driver Patrizio was very prompt and professional,” highlighting the seamless experience.
Bottom line: This tour offers excellent value for wine enthusiasts who want a comprehensive day of tasting, cultural exploration, and authentic Tuscan cuisine without the stress of self-driving. It’s ideal for couples, honeymooners, or anyone eager to indulge in Tuscany’s wine and food scene.
2. PRIVATE TOUR: Full-Day Volterra & San Gimignano with Wine Tasting Experience
Number two on our list is a private tour that covers two of Tuscany’s most picturesque hill towns in about seven hours. This trip is all about convenience and flexibility—no need to puzzle over public transport schedules. Your driver will pick you up from Siena and whisk you through the rolling Tuscan landscape, passing vineyards, olive groves, and sunflower fields.
You’ll explore Volterra, famous for its Etruscan roots, Roman theater, and medieval streets, at your own pace. The self-guided component allows you to linger or rush, depending on your interests. Afterward, the tour heads to a family-run organic farm in Chianti for a relaxed lunch and wine tasting of five different wines. This experience earns high marks from reviews, with travelers praising the friendly guide Stefano and the chance to enjoy the scenery and wines in a calm, personalized setting.
The highlight here is the combination of cultural exploration and gourmet food, making it suitable for travelers who want to absorb history while enjoying good wine and fresh food. It’s particularly good for small groups or couples who value comfort and flexibility.
Bottom line: For a tailored, hassle-free day exploring two top towns with a delicious Chianti lunch, this private tour is a smart pick—especially if you prefer avoiding crowded groups and enjoy customizing your itinerary.
3. Full-Day Chianti Tour by Vespa Scooter from San Gimignano
Number three offers a more adventurous approach: a Vespa tour through the Chianti region. For around seven and a half hours, you’ll hop aboard a Vespa and cruise through some of Italy’s most iconic landscapes. This tour is best suited for energetic travelers comfortable on two wheels—whether you choose to drive or ride as a passenger.
The route includes Radda in Chianti, where you’ll take photos of the stunning scenery, and a visit to Casale dello Sparviero, a working farm and winery. Here, you’ll enjoy a wine tasting and a light Tuscan lunch amid cypress-lined avenues. The route also offers free time in the medieval village of Monteriggioni, perfect for wandering narrow streets and soaking in the ambiance.
Reviewers note the fun of riding a Vespa, but some mention that the rating is average (3.5/5), mainly due to the physical demands and the need for a sense of adventure. The experience is ideal for those seeking a lively, active day with an authentic taste of Chianti’s rolling hills and vineyards.
Bottom line: If you’re up for a fun, outdoor way to see Tuscany—preferably with some riding skills—this Vespa tour provides a memorable twist on a wine and countryside day.
$168.00 per person
How to Choose
When deciding among these tours, consider your interests and travel style. For wine lovers eager to taste Brunello and experience local food in a relaxed setting, the full-day winery tour is hard to beat. If you prefer exploring historic towns with a private guide and a customizable pace, then the private day trip suits you well. For an active, fun-filled day that combines sightseeing with a bit of adventure, the Vespa Chianti tour offers something unique.
Also think about your budget—this ranges from about $168 for the Vespa tour to $381.99 for the full-day wine experience. Time-wise, all are around 7-8 hours, but private tours offer more flexibility. If you’re a wine enthusiast, the first two tours are especially appealing. For those wanting a more active experience, the Vespa trip might be your best fit.
Make sure to book early, especially in peak season, to secure your preferred date and avoid missing out.
Final Thoughts
Siena’s central location makes it a perfect jumping-off point for a variety of full-day adventures. Whether you’re after wine and food, exploring ancient towns with a private guide, or cruising the Chianti hills on a Vespa, there’s an option tailored to your interests. The full-day wine tour in Montepulciano stands out for its blend of excellent value, gourmet food, and memorable scenery. Meanwhile, the private day trip offers comfort and flexibility, perfect for those who want a personalized experience. Lastly, the Vespa ride adds a dash of excitement for active travelers.
No matter what you choose, these tours are a fantastic way to make the most of your time in Siena and truly get a taste of Tuscany’s flavors and landscapes. Book early, plan ahead, and enjoy a full day of authentic Tuscan memories.