Top Things to Do in Montepulciano: Experiences, Prices & Booking Guide

If you are planning a getaway to the rolling hills of Tuscany and wondering about the best things to do in Montepulciano, you have come to the right place. Beyond its postcard-perfect views, this world-renowned hilltop town offers a wide array of immersive activities that allow you to experience authentic Tuscan culture firsthand.

Whether you are organizing a romantic weekend, a day trip, or an extended holiday, booking your Montepulciano experiences in advance ensures you lock in the best rates and secure your spot on top-rated tours, which frequently sell out.

In this guide, we break down the most popular activities for travelers, complete with updated prices, durations, and booking flexibility. All recommended tours feature free cancellation up to 24 hours in advance and a “reserve now, pay later” option, allowing you to secure your itinerary completely risk-free.

Best Guided Experiences to Book in Montepulciano

Montepulciano is defined by its relaxed pace of life, rich culinary heritage, and world-class winemaking traditions.

Below is a detailed overview of the top 3 most requested activities among international travelers, along with a quick comparison table to help you select the ideal experience for your trip.

Experience Comparison Table

Horseback Riding Through Montepulciano Vineyards with Tasting

Riding through the Tuscan countryside on horseback is one of the most memorable ways to connect with Montepulciano’s natural landscape. This 1.5-hour small-group tour (capped at just 8 participants) departs directly from the stables and is suitable for all experience levels—from absolute beginners to seasoned riders—under the guidance of expert multilingual instructors (English, Italian, and French).

The trail winds through lush vineyards, ancient olive groves, and panoramic paths offering sweeping views over the Tuscan hills. Upon returning to the estate, you will tour the farm before sitting down to enjoy a selection of local specialties (such as regional cheeses, artisanal cold cuts, traditional bruschetta with extra virgin olive oil, or local pastries paired with regional wines).

• Price: €85 per person (taxes and fees included).

• What’s Included: Horseback riding equipment, assigned horse, professional guide, farm visit, and a tasting of local food and drinks.

• Flexibility: Free cancellation up to 24 hours before the activity for a full refund. “Reserve now & pay later” available.

If you want to treat yourself to a unique outdoor adventure:

👉 Check available dates and book the horseback riding tour on GetYourGuide

Montepulciano: Truffle Hunting in the Tuscan Countryside

Truffle hunting is an authentic, hands-on activity ideal for foodies and nature enthusiasts. Led by a local truffle hunter (tartufaio) and trained hound dogs, you will venture into the forest to learn the secrets behind foraging for one of Italy’s most prized delicacies.

This 2.5-hour experience begins at the Fattoria della Talosa offices in Montepulciano with a brief introduction to how truffles grow and how the dogs are trained. You will then follow the guide in your own vehicle to the search site (approx. 15 minutes away) for a 1-hour and 15-minute hunt through the woods. It is a great outdoor experience for adults and families alike (hiking shoes and comfortable outdoor clothing are required).

• Price: From €104 per person (promotional discount from €130; prices vary by date).

• What’s Included: Local truffle hunter guide, trained truffle dogs, and an introductory lesson on search techniques.

• Flexibility: Free cancellation up to 24 hours prior and flexible booking options with no upfront charge.

Spaces for this private forest hunt are strictly limited:

👉 Check updated prices and reserve your truffle hunting slot on GetYourGuide

Montepulciano: Wine Tasting & Underground Cellar Tour

No trip to Montepulciano is complete without discovering its historic underground wine cellars. Located in the heart of the medieval town center, this guided tour takes you behind the scenes of centuries-old winemaking traditions, famous for aging Vino Nobile di Montepulciano in massive oak barrels made of Slavonian and French oak.

During the 1-hour visit, your guide will explain the unique tufa soil composition (rich in ancient fossils) and lead you through the barrel aging vaults. The tour concludes with a guided tasting of 5 DOC and DOCG Montepulciano wines, paired with local crostini, bruschetta drizzled with extra virgin olive oil, and aged Tuscan pecorino cheeses.

• Price: €33 per person (taxes and fees included).

• What’s Included: Live tour guide (English/Italian), cellar admission, guided tasting of 5 DOC/DOCG wines, pecorino cheese sampling, bruschetta, and crostini.

• Flexibility: Free cancellation up to 24 hours before start time. Hold your spot today and pay later.

As the most popular tour in the area (rated 5 stars by over 94% of Italian and international travelers):

👉 Click here to check start times and lock in your wine tasting tickets on GetYourGuide

Where to Stay for an Exclusive Tuscan Getaway

After a day spent riding through vineyards, searching for wild truffles in the forest, or sampling Vino Nobile in underground cellars, the best way to round out your itinerary is with an authentic luxury stay.

For accommodation in Montepulciano and across the surrounding Val d’Orcia region, consider booking a private stay with Tuscan Mansions. Featuring historic estates, luxury amenities, private swimming pools, and sweeping views of the countryside, these villas provide the ultimate home base for an unforgettable Italian holiday.

👉 Explore luxury villas and book your stay at Tuscan Mansions