Practical walking tours define the best way to experience this classic Tuscan hill town. The most worthwhile outings combine food, wine, and history in compact 2-3 hour formats.
Smart travelers opt for morning tours that include tastings of local specialties – pecorino cheese, salami, and fresh pasta – along with cellar visits in historic palazzos.
The town’s medieval lanes and epic bell tower views are best explored with knowledgeable local guides who share authentic insights without tourist gimmicks.
For wine enthusiasts, private winery tours offer intimate tastings and food pairings that showcase Montepulciano’s famous Vino Nobile.
Below are our favorite walking tours, ranked for value and authentic experiences.
Good To Know
- The Gourmet Tour in the Old Town Center offers a private tasting experience with local specialties and a guided cellar tour for an average rating of 4.5 out of 5.
- The Montepulciano Walking Tour and Wine Toast provides a knowledgeable guide, exploration of the medieval town, and an optional bell tower climb with prices starting from $54.21 per person.
- The private 2 Hours – Private Walking Tour in Montepulciano focuses on the town’s history and architecture, with a coffee or tea break and access to the Comune di Montepulciano.
- The Guided Walking Tour and Food Tasting offers a 3-hour experience showcasing Montepulciano’s heritage, breathtaking views, and local specialties, priced at $143.86 per person.
- The Discovering PODERE CASANOVA Winery tour provides a private guided exploration of the vineyards and a tasting of Tuscan cheeses, cured meats, and wines.
Montepulciano Walking Tour With Food and Wine Tastings
Although there are several walking tours available in Montepulciano, the “Gourmet Tour in the Old Town Center” from Valdichiana Living stands out as a popular option.
This private tour takes visitors on a leisurely stroll through the historic old town center, with stops for tastings of local Pecorino cheese, salami, bruschetta, and handmade Pici pasta. The highlight is a guided tour of an underground cellar where participants can sample the renowned Vino Nobile di Montepulciano DOCG wine.
With an average rating of 4.5 out of 5 from 12 reviews, this tour receives positive feedback for its knowledgeable and engaging guide, as well as the overall enjoyable experience of discovering the local flavors.
Some participants, however, wished for more historical context about the city. The tour is priced at €135 per person, with free cancellation up to 24 hours in advance.
Reservations are recommended to secure a spot, as the tour is likely to sell out.
Read our full review: Montepulciano Walking Tour With Food and Wine Tastings Review
Book now: Check availability
Montepulciano Walking Tour and Wine Toast
One of the most popular walking tours in Montepulciano is the “Montepulciano Walking Tour and Wine Toast”. This 93% traveler-recommended tour offers an immersive exploration of the medieval hill town, led by a knowledgeable guide.
Participants will stroll through the picturesque lanes, taking in the historical ambiance, and have the option to climb the bell tower for panoramic views, at their own expense.
The tour starts at the Piazzetta al Prato and ends at the Piazza Grande, with a tasting of the renowned Vino Nobile di Montepulciano as the grand finale.
Depending on the day, the tour runs either from 10:00 AM to 12:30 PM and 3:00 PM to 5:00 PM, or from 10:00 AM to 12:30 PM and 3:00 PM to 5:30 PM.
With a maximum group size of 15 and accessibility for wheelchairs and strollers, this tour caters to a wide range of travelers.
Prices start from $54.21 per person, and free cancellation is available up to 24 hours before the experience.
Read our full review: Montepulciano Walking Tour and Wine Toast Review
Book now: Check availability
2 Hours – Private Walking Tour in Montepulciano
Embarking on a private walking tour of Montepulciano allows visitors to explore the town’s rich history and captivating architecture at their own pace. The 2-hour experience takes guests on an immersive journey, starting at the threshold of the church in Piazza Santa Agnese.
Along the way, they’ll have the option to enjoy a refreshing coffee or tea break, as well as gain access to the Comune di Montepulciano, with admission fees included.
The tour is wheelchair and stroller accessible, and transportation options are available for those who need them. At the end, visitors will arrive at a different location, with the details provided upon booking.
Flexibility is key, as the tour can accommodate a range of group sizes, with prices starting from $140.94 per person, subject to group size.
Boasting a perfect 5.0-star rating from 4 reviews, this private walking tour promises an engaging and immersive exploration of Montepulciano’s captivating charms.
Read our full review: 2 Hours – Private Walking Tour in Montepulciano Review
Book now: Check availability
Montepulciano: Guided Walking Tour and Food Tasting
Montepulciano’s Guided Walking Tour and Food Tasting offers visitors a captivating exploration of the town’s rich heritage and culinary delights.
This 3-hour experience, priced at $143.86 per person, guides travelers through Montepulciano’s historic center, showcasing its breathtaking views and local specialties.
Led by knowledgeable guides in English or Italian, the tour includes visits to a local store, restaurant, and an underground wine cellar, where participants can sample pecorino cheese, salami, and handmade Pici pasta.
The highlight is a guided wine tasting featuring the renowned Vino Nobile di Montepulciano.
With a 4/5 rating based on 4 reviews, the tour receives praise for the guide’s expertise and kindness, though some participants suggest a more diverse selection of food options.
Read our full review: Montepulciano: Guided Walking Tour and Food Tasting Review
Book now: Check availability
Discovering PODERE CASANOVA Winery, Walking and Wine Tasting With Lunch
Nestled amidst the rolling hills of Montepulciano, the Podere Casanova Winery beckons travelers to explore a captivating experience of walking and wine tasting accompanied by a savory lunch.
This private tour allows your group to explore the vineyards, guided by knowledgeable hosts, and indulge in a tasting of the winery’s acclaimed offerings.
As you meander through the scenic landscape, you’ll be treated to a platter of Tuscan cheeses and cured meats, perfectly paired with the wines.
The meeting and end point is at the winery itself, providing a seamless start and finish to your adventure.
With confirmation typically received within 48 hours and a lowest price guarantee, this experience promises an unforgettable day of discovery in the heart of Montepulciano.
Most travelers can participate, though it’s not wheelchair accessible, and infants must sit on laps.
Read our full review: Discovering PODERE CASANOVA Winery, Walking and Wine Tasting With Lunch Review
Book now: Check availability
Questions About Staying Here
How Fit Do I Need to Be for the Walking Tours?
The fitness level required for walking tours can vary, but most are suitable for participants with a moderate level of physical fitness. Comfortable shoes and a willingness to walk for extended periods are typically the main requirements.
Are the Tours Wheelchair or Stroller Accessible?
The walking tours may not be fully accessible for those in wheelchairs or with strollers. The cobblestone streets and hills can make navigation difficult. It’s best to inquire with the tour operators about accessibility accommodations before booking.
Can I Take Photographs During the Walking Tours?
Yes, most walking tours allow participants to take photographs during the tour. However, visitors should be mindful not to disrupt the guide or other tour members and follow any specific photography policies the tour operator may have.
What Should I Bring for the Wine Tastings?
For wine tastings, visitors should bring an open mind, comfortable shoes, and a small notebook to jot down their thoughts and impressions of the wines. It’s also wise to stay hydrated and avoid heavy meals beforehand.
Are the Walking Tours Suitable for Children?
The walking tours are generally suitable for children, but it’s best to check with the tour operator beforehand. Some tours may have age restrictions or activities that aren’t appropriate for young kids. It’s a good idea to inquire about child-friendly options.
Worth The Stay
Montepulciano offers a variety of walking tours that showcase the town’s historic charm, local cuisine, and renowned wines. From private tours to group experiences, visitors can enjoy the rich culture and flavors of this Tuscan gem. Whether seeking a quick overview or a more in-depth exploration, there’s a walking tour suited to every traveler’s interests and preferences.