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Make the most of your time in Montepulciano with this walking tour that takes in the highlights of the medieval hill town in just hours. Skip the dry guidebook and visit with a guide who can make the Tuscan town’s history to life as you stroll the picturesque lanes and climb to the top of the bell tower (own expense) to admire the views. End with a glass of local wine to cap off your visit.
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Discover Montepulciano!
2 hours
to
2 hours 30 minutes
Free Cancellation
4.8
(17)
5% savings
from
$57
$54
Member Pricing
Explore a wine cellar in Montepulciano with this tasting and tour. See rows of large oak barrels full of aging wine and learn about how it is made. Taste 3–6 local wines— Supertuscan, Nobile, and Nobile Riserva—alongside a food tasting or bruschetta with extra-virgin olive oil.
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Tasting Tour in One of The Most Beautiful Cellars in the World
1 hour
Free Cancellation
4.8
(296)
5% savings
from
$38
$36
Member Pricing
Start a suggestive walk through olive trees and vineyards, discovering the secrets of harvesting white grapes for the wine you will taste. Get up close and personal with the historic Tuscan Cinta Senese breed and meet Otto, the 300kg breeding pig. Walk through the garden to admire seasonal vegetables. Visit the ripening room to discover local cold cuts. End the tour with a tasting that includes two types of bruschetta and a platter of artisanal cold cuts, accompanied by a glass of house wine.
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Visit to the Farm with Tasting of Cold cuts and bruschetta
1 hour 30 minutes
Free Cancellation
5.0
(3)
5% savings
from
$32
$30
Member Pricing
Meet Ciro, the domestic pig, on this small-group tour of the Cinta Senese farmhouse. You’ll also meet Roberto, the local farmer, who will tell you all about the pigs at the farmhouse. Over the course of the tour you’ll have a light lunch featuring a local wine tasting plus cold cuts, Pecorino di Pienza cheese, and much more.
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Montepulciano: Cinta Senese Farm Tour, Food Tasting & wine
2 hours
Free Cancellation
4.8
(25)
5% savings
from
$66
$63
Member Pricing
This experience offers the perfect blend of adventure, culture, and local flavor. Ride effortlessly through the scenic Tuscan hills with an expert guide, visit a small family-run winery for an authentic 4-wine tasting. What makes it truly special is the final stop at our farm, where you'll meet the rare Cinta Senese pigs, a centuries-old Tuscan breed raised with care. It's not just a bike tour—it’s a deep dive into Tuscany’s land, traditions, and tastes.
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E-Bike Tour in the Tuscan Hills with Wine Tasting
2 hours 30 minutes
Free Cancellation
5.0
(14
Operators
)
5% savings
from
$263
$250
Price varies by group size
Member Pricing
The experience is distinguished by the departure DA a real Tuscan farm, the use of comfortable e-bikes with double suspension and the Guide of a Destination Expert who will make you discover hidden corners, stories and traditions of the Montepulciano hills. You will cross authentic landscapes among vineyards, ancient churches and spectacular views, experiencing Tuscany more genuine and far from mass tourism. Book now for an unforgettable adventure!
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E-bike tour Montepulciano and Val d’Orcia with Guide
3 hours
Free Cancellation
5.0
(93
Operators
)
5% savings
from
$286
$272
Per group
Member Pricing
Discover Montepulciano and the Val d’Orcia in complete freedom, without Guide and without using your smartphone. The rental includes good quality e-bikes, bi-cushioned and comfortable even on dirt roads, with high capacity batteries suitable for long distances. Each bike is supplied with a dedicated GPS navigator and selected routes already loaded, to easily follow scenic roads, vineyards, olive groves and historic villages. You can ride at your own pace, stop when you want and experience Tuscany without rigid schedules or groups to follow. Before departure you will receive all the necessary explanations about the e-bike and the navigator, with assistance available during the rental.
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E-Bike Rental in Montepulciano GPS Navigator and Included Routes
1 to 8 hours
Free Cancellation
5.0
(93
Operators
)
5% savings
from
$74
$71
Member Pricing
Learn how to make two types of homemade Italian pasta—topped off by a tasty tiramisu dessert—during this small-group cooking workshop in Montepulciano. Head to the home of a local Tuscan cook and enjoy an intimate class in a group capped at 12 people. A tasting of your creations is included, paired with wine and prosecco.
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Montepulciano: Pasta & Tiramisu Class in a Local Home by Cesarine
3 hours
Free Cancellation
4.9
(154)
5% savings
from
$74
$71
Member Pricing
The Montepulciano tour will allow you to discover one of the most fascinating towns of the area, the so-called “Renaissance pearl” sheltered inside Medieval city walls. We will start our tour on the summit of the town, in the magical Piazza Grande, where we will be able to visit the never-finished Cathedral, see the main Gouvernment Palace, the Palaces Contucci and Tarugi, the beautiful 1500 well, and enjoy a wonderful view over the Val di Chiana and part of the Val d'Orcia. We will then descend the town, following the winding main street, thereby admiring Montepulciano's wonderful palaces and churches along the way. We will learn about its traditions … for example:– did you know that once a year they have a barrel-pushing competition? – , and spot all the movie sets of the town! Last but not least, our tour will take us underground to visit one of the ancient wineries of the town, and taste a glass (or more!) of Nobile wine. IMPORTANT: the tour schedule in the system is 10am and 15pm, but the tour times can be arranged directly with the guide upon request.
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Private Guided Tour of Montepulciano with wine tasting
2 hours
Free Cancellation
4.9
(17)
5% savings
from
$152
$144
Price varies by group size
Member Pricing
This experience is different from classic sightseeing because it combines a creative activity, authentic Tuscan farm life and a traditional lunch. Guests take part in an interactive workshop of handcrafted soaps, where they can create their own personalized soap by choosing colors, scents and molds in the shape of animals such as alpacas or piglets. It is a fun and relaxing activity, suitable for couples, families and small groups. The experience continues with a visit to a real Tuscan farm, where guests will discover the breeding of Cinta Senese pigs, one of the oldest and most representative breeds in Tuscany. The tour ends with a typical Tuscan lunch on the farm, prepared with local products and ingredients from the countryside. This experience allows travelers to experience the Tuscan countryside in an authentic way, actively participating and bringing home a bar of soap made with their own hands as a unique souvenir of the day.
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Create your own Soap in Fattoria Tour Cinta and Tuscan Lunch
3 hours 30 minutes
Free Cancellation
5.0
(14
Operators
)
5% savings
from
$103
$98
Member Pricing
Combine two of Montepulciano’s highlights—spectacular landscapes and world-class wine—in a single experience with this Vespa tour through the countryside plus wine tasting lunch at a local cellar. Zip through the Val d’Orcia or around Lake Trasimeno on an iconic Vespa scooter (drive yourself or opt to ride with a driver), stopping to snap photos and admire the view. Then end with a wine-tasting lunch at a winery in the Montepulciano hills.
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Romantic Vespa Tour and Wine Tasting
5 hours
4.9
(7)
5% savings
from
$297
$282
Member Pricing
The private e-bike tour starts from Montepulciano and develops a circular route towards Pienza and Monticchiello, crossing some of the most iconic landscapes of the Val d'Orcia. The route measures about 38 km with 684 m of positive elevation gain and altitudes between 321 and 546 m: intermediate level. The indicative duration is 4-5 hours, excluding stops. The itinerary alternates paved secondary roads, dirt roads, stretches of countryside, and panoramic ups and downs, with possible short sections open to traffic. During the tour, you cycle through hills, cypress trees, estates, and continuous views of the Tuscan countryside. Pienza, with its historic center recognized by UNESCO, represents one of the main stops, while Monticchiello retains a more intimate and medieval character, ideal for a break. The tour is scenic and not technical, but it features climbs to tackle at a regular pace. It is recommended especially in spring and autumn; in summer it is preferable to leave early in the morning.
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Montepulciano Val d'Orcia E-Bike Tour to Pienza and Monticchiello
4 to 5 hours
Free Cancellation
5% savings
from
$89
$85
Member Pricing
After Reservation, the tour starts at the rental point with the collection of e-bikes and the activation of virtual navigation, which accompanies along the way. The loop route measures about 32.2 km and has 597 m of positive altitude difference: medium level. It starts from Montepulciano and crosses some of the most recognizable landscapes of the Val d’Orcia, alternating paved roads, short stretches on a state road, paths and quiet side roads. The route passes near the Temple of San Biagio and continues through vineyards, olive groves, cultivated hills and panoramic points. The famous rows of cypress trees accompany the ride to Monticchiello, where you can stop for a break in the village or at the Osteria La Porta. The return to Montepulciano follows hilly roads with new views of the Tuscan countryside, completing an experience that combines landscape, culture and local flavors. Particular caution is required in sections shared with traffic.
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Montepulciano countryside E-bike virtual guided tour
3 to 4 hours
Free Cancellation
1.0
(1)
5% savings
from
$89
$85
Member Pricing
Certo, ecco la traduzione in inglese: This tour is designed for true wine lovers who wish to discover Montepulciano through its wines and wineries, enjoying a full immersion into the world of Vino Nobile di Montepulciano. Accompanied by a professional driver, you will visit three selected wineries, each with its own identity and production philosophy. Through guided tastings of Rosso di Montepulciano DOC and Vino Nobile di Montepulciano DOCG, you will have the opportunity to compare different production styles and observe how the same grape variety and territory can give rise to wines with different expressions. During the visits, you will discover how vineyard choices, winemaking techniques, and ageing methods influence the character of each wine, revealing the diversity of Vino Nobile di Montepulciano. At the second winery, the tour includes a traditional Tuscan light lunch, served at the winery and accompanied by local products, offering a pleasant break between tastings.
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Wine lovers experience in Montepulciano: full day
6 hours
Free Cancellation
4.4
(5)
5% savings
from
$401
$381
Member Pricing
Rent an electric bicycle in Montepulciano and visit the wineries of Tuscany without getting too tired. Thanks to the extra sprint it gives you over hilly terrain, the electric bike is the perfect way to explore the country lanes and soak up the landscape of the famous wine region. Following a planned route, you will be able to visit a selection of local wineries and enjoy two wine tastings in their cellars.
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Wine Tour Ebike Experience
5 hours
Free Cancellation
4.9
(184)
5% savings
from
$182
$173
Member Pricing
This is not a standard tour, but an authentic walk with a local Guide who lives in Montepulciano. The pace is relaxed and the experience is designed to suit the interests of the participants, including stories, lesser-known corners and a tasting of Rosso di Montepulciano in a selected wine shop.
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Montepulciano Private Walking Tour with Wine Tasting
2 hours
Free Cancellation
5.0
(14
Operators
)
5% savings
from
$155
$147
Price varies by group size
Member Pricing
Explore the beautiful medieval town of Montepulciano on this leisurely private walking tour. Enjoy the undivided attention of your private guide as you wander around the charming Piazza Grande and climb the tower of the Palazzo Comunale, taking in views of the surrounding countryside. Stop to enjoy a closer look at attractions and snap photos of the sights that interest you most.
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2 hours - Private Walking Tour in Montepulciano
2 to 3 hours
5.0
(7)
5% savings
from
$149
$141
Price varies by group size
Member Pricing
It is the right choice for those who want to experience the symbolic area of Tuscany, a UNESCO heritage site, being able to stop from village to village to taste a good ice cream or go shopping in some local shop Ideal for: movie buffs dying to take a selfie like Russell Crowe in Gladiator Those who want to visit the Val d'Orcia and its pearls Monticchiello and Pienza in total autonomy and provacy, without needing a guide to accompany you with the relevant additional cost. P.s.: Our staff will always be in contact in case of need, even if necessary with the intervention of our assistance van. NATURE & FAMILY
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E-Bike Val d'Orcia Experience
4 to 6 hours
Free Cancellation
4.9
(27)
5% savings
from
$178
$169
Member Pricing
This tour is dedicated to true wine enthusiasts who wish to explore Montepulciano through its wines, people, and traditions, enjoying a complete immersion into the world of Vino Nobile di Montepulciano. With a professional driver, you will visit two carefully selected wineries in the Montepulciano area. At each estate, you will discover the history of the territory and the winemaking philosophy of the producers, learning about the key stages of wine production, from vineyard to bottle. The experience includes guided tastings of Rosso di Montepulciano DOC and Vino Nobile di Montepulciano DOCG, allowing you to fully appreciate the elegance and character of these iconic Tuscan wines. At the second winery, the tour is enriched with a traditional Tuscan light lunch, served in the cellar and paired with local products, offering the perfect moment to relax and savor the authentic flavors of the region.
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Wine lovers experience in Montepulciano: half day
4 hours
Free Cancellation
4.2
(5)
5% savings
from
$349
$332
Price varies by group size
Member Pricing
The medieval hilltop town of Montepulciano is set in Tuscany's culinary heart. Experience both the local culture and cuisine with this tour that combines a guided walk through Montepulciano's old town with a number of food and wine breaks. Learn about the town's history and architecture between stops at a local gourmet shop, traditional restaurant, and wine cellar to taste local cheeses and charcuterie, handmade pasta, and wine.
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Gourmet tour in the Montepulciano old town center
3 hours
Free Cancellation
4.1
(15)
5% savings
from
$155
$147
Member Pricing
Roberto gets to know his pigs one by one; they are raised in a semi-wild state, with carefully selected feed and cereals grown in the Tuscan countryside. The experience is as rural as it is unforgettable; after a walk through the vineyards and olive grove, you will have the opportunity to interact with "Ciro", or the domestic pig, and to meet his entire company of Cinta Senese pigs having fun in the mud. after meeting these cute animals (and maybe even taking some selfies with them), it will be time to delight your palate with a dinner based on local products
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Cinta Senese tour with tasting dinner on the farm
2 hours 30 minutes
Free Cancellation
5.0
(4)
5% savings
from
$74
$71
Member Pricing
The medieval center of Montepulciano stands on the historic cellars hidden below the city. With this exclusive tour, take a guided walk in the historic center and visit two underground cellars, venture into the tunnels carved into the rock to admire the impressive oak barrels where the Vino Nobile di Montepulciano is left to age. Learn about the history of wine and how it is produced in this area and taste the local vintages.
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Tour of the historical cellars in Montepulciano
2 hours 30 minutes
Free Cancellation
3.9
(27)
5% savings
from
$90
$86
Member Pricing
Few bottles that contain the maximum expression of the terroir. The ideal tour for true wine experts. Montepulciano, as we know, is the land of wine. Walking through the streets of the historic center or crossing the hilly landscapes that surround it, it is easy to see vineyards, wineries and wine bars almost everywhere. With this tour you will get to know those small producers of Vino Nobile di Montepulciano DOCG, whose bottles contain the maximum expression of the local terrior.
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Wine Tour of the small producers in Montepulciano
3 hours
Free Cancellation
4.5
(199
Operators
)
5% savings
from
$166
$158
Member Pricing
At Fattoria Madonna della Querce, every experience is authentic and personal. This is not a standard tour, but a real day on a working Tuscan farm — surrounded by nature, animals, and the people who keep traditions alive. The horseback ride takes you through rolling hills, vineyards, and scenic white roads, while the farm visit lets you meet the Cinta Senese pigs, raised outdoors with care and respect. Lunch is homemade using fresh local ingredients and shared in a warm, family-style atmosphere. An intimate, genuine experience — far from mass tourism — that lets you feel the real heart of Tuscany.
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Horseback Ride Farm Visit and Lunch at Montepulciano
3 hours 30 minutes
Free Cancellation
5.0
(1)
5% savings
from
$263
$250
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