If you are planning a trip to Tuscany, you have probably wondered what to do in Montepulciano to truly capture the essence of this medieval hilltop gem nestled between Val d’Orcia and Valdichiana. Renowned worldwide for its postcard-perfect landscapes, Renaissance architecture, and, of course, the legendary Vino Nobile, this village offers unique activities that can turn a simple vacation into a lifelong memory.
Whether you are a dedicated foodie, a wine connoisseur, or an outdoor adventurer looking for breathtaking views, you will find plenty of options. However, Montepulciano’s most exclusive and top-rated activities operate with strict group limits and tend to sell out months in advance. To help you lock in your spot at the lowest guaranteed price, we have curated the absolute best Montepulciano experiences available on Viator—all featuring ultimate flexibility and free cancellation.
Must-Try Experiences in Montepulciano: Quick Guide & Prices
Before diving into the details of each activity, check out this quick comparison table. It allows you to check starting prices, duration, and find the perfect fit for your itinerary. All featured experiences offer free cancellation up to 24 hours before the event and a “Reserve Now & Pay Later” option to give you complete travel flexibility.
| Experience | Duration | Price per Person | Highlights | Cancellation |
| Historic Cellar Tour & Tasting | 1 hour (approx.) | From €33.00 | Located in the old town; De Ricci wine pairings | Free (24h notice) |
| Vineyard Horseback Riding | 1.5 hours (approx.) | From €80.00 | Beginner-friendly; immersive nature trail | Free (24h notice) |
| Pasta & Tiramisù Class (Cesarine) | 3 hours (approx.) | From €65.00 | Intimate local home cooking & dining experience | Free (24h notice) |
| Tuscan Vineyard Picnic & Wine Tour | 2 hours (approx.) | From €85.00 | Guided cellar tour & private picnic in the vines | Free (24h notice) |
| Self-Guided Virtual E-Bike Tour | 3-4 hours (approx.) | From €90.00 | Total freedom; 36 km of panoramic scenery | Free (24h notice) |
Tour and Tasting in One of the Most Beautiful Cellars in the World
If you are looking for the ultimate Montepulciano wine tasting, this tour is the perfect place to start. Located right in the heart of the historic center (on Via Ricci), this experience guides you through a monumental historic cellar where you will walk among massive Slavonian oak and French wooden barrels.
Highly recommended by 96% of travelers, this activity unveils the secrets behind local winemaking. You will get to sample 3 to 6 glasses of the finest local wines—including Supertuscan, Rosso, Nobile, and Nobile Riserva—expertly paired with traditional bruschetta drizzled with local extra virgin olive oil. The tour is limited to a maximum of 15 participants to ensure an intimate and personalized atmosphere.
Price: From €33.00 per person (Discounted rates available for children).
Insider Tip: The winery is inside a pedestrian-only zone. We highly recommend parking at “Parcheggio S. Donato” or “Parcheggio P8”.
Vineyard Horseback Riding in Montepulciano Tuscany
For those who want to combine a love for nature with a bit of adventure, this horseback trail ride is one of the best outdoor experiences in Montepulciano. The tour sets off from a charming countryside estate in Località Bertille, taking you along scenic paths and through rolling vineyards with stunning views over the Tuscan hills.
No prior riding experience is required: professional guides will pair you with the perfect horse and assist you every step of the way. Upon returning to the stables, you can unwind and chat about your ride over a fresh glass of local wine or a warm cup of coffee. With a strict maximum of 8 participants, this tour feels exceptionally exclusive.
Price: From €80.00 per person.
Safety Note: This activity is not recommended for pregnant travelers or anyone with back issues.
Montepulciano: Cooking Class – Pasta & Tiramisù with a Local Host
What could be more authentic than learning the secrets of Tuscan cuisine inside a private home? This exceptional masterclass, hosted by a certified “Cesarina” (a local home cook guarding generational family recipes), offers a hands-on opportunity to craft two iconic types of fresh pasta (including regional pici) and a classic tiramisù from scratch.
Earning a Badge of Excellence on Montepulciano Viator, this experience kicks off with a welcoming Italian aperitivo featuring prosecco and local finger foods. It concludes with a sit-down lunch or dinner enjoying your own culinary creations, beautifully paired with a selection of regional DOC and DOCG wines. This 5-star foodie experience is limited to just 12 guests for maximum interaction.
Price: From €65.00 per person.
What’s Included: Aprons, cooking utensils, all food, wine, and coffee. For privacy reasons, the host’s exact address will be shared immediately after booking.
[CHECK AVAILABILITY FOR THE CESARINE COOKING CLASS ON VIATOR]
Tuscan Picnic: Discovering the Vino Nobile di Montepulciano
For a romantic or laid-back day out in the countryside, this Montepulciano tour pairs a classic wine cellar visit with an exclusive open-air lunch. The journey begins at Piazza Grande at the Valdichiana Living office, where your included round-trip transport waits to take you to a local estate.
After touring the cellar and learning the secrets behind the prestigious Vino Nobile di Montepulciano DOCG, you will head out directly into the vineyards. There, a delicious Tuscan picnic basket awaits, packed with authentic local delicacies (cured meats, artisanal cheeses) and a bottle of Rosso di Montepulciano (one bottle for every 4 guests). It is the ultimate way to unplug and dine while surrounded by the sweeping vistas of the Val d’Orcia.
Price: From €85.00 per person.
What’s Included: Guided cellar tour, picnic basket, wine, and round-trip transfer from the meeting point.
Montepulciano Countryside E-Bike Tour (Virtually Guided)
If you love active exploration at your own pace, a self-guided e-bike tour of the Montepulciano countryside is a phenomenal choice. Pick up your premium electric bicycle at the rental hub on Via delle Lettere and set off on a gorgeous 36 km (22-mile) loop. No need to worry about getting lost: a virtual guide app (Outdoora) provides turn-by-turn navigation and voice assistance throughout the ride.
You will breeze up the hills effortlessly thanks to the electric assist, cruising along panoramic gravel roads and passing iconic spots like the San Biagio Church, the medieval village of Monticchiello, and spectacular viewpoints facing Val d’Orcia and Mount Amiata. The itinerary also suggests fantastic, optional independent stops along the way, such as the Cugusi Dairy or historic wineries. Because this is a digitally-guided private tour, you travel strictly with your own group and on your own schedule.
Price: From €90.00 per person.
What’s Included: E-bike rental, phone holder, remote support, app access, and special partner discounts along the route.
Stay in Ultimate Luxury: The Villas of TuscanMansions
After checking off the best things to do in Montepulciano—from wine tastings and horseback rides to e-bike excursions—there is nothing quite like relaxing in a dream property that mirrors the elegance of the Tuscan landscape.
To elevate your getaway into a truly unforgettable experience, look no further than the exclusive portfolio of TuscanMansions. Tucked away in the region’s most scenic and strategic locations, these luxury villas feature sophisticated interiors, private swimming pools, beautifully manicured gardens, and top-tier modern amenities, all while preserving the historic charm of traditional Tuscan estates. Treat yourself to the stay you deserve: visit the official TuscanMansions website today and secure your private villa for an unforgettable vacation in the heart of Tuscany.
