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39 results
Best Seller
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
(287)
from
$38
Likely to Sell Out
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
(139)
from
$75
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
4.5
(9 Operators)
from
$104
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
(21)
from
$68
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
5.0
(179)
from
$184
Book now the best tour with photographic experience in the heart of Valdorcia in Tuscany, to have magnificent memories of your trip with your partner or family. On this tour you will enjoy the wonderful enchanted landscapes typical of Tuscany and also the fascinating and hidden places, outside the usual guided tours for tourists, living a real dream. You will become a photo model for a day and you will feel like a real movie star, in the places that have become famous for some famous films such as "The Gladiator", "Life is Beautiful", "Twilight", "Nostalgia", Fellini's "8 & 1" /2" and many others. The tour is "All in One", it means that everything is included: tour + guide + photos + transportation (if necessary). All this for the price of a simple guided tour. And the photos we take will probably be the best you've ever taken. Let yourself be carried away on this adventure with your personal photographer and guide on a tour that will literally leave you speechless.
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Photography Guided Tour in the Heart of Val D'Orcia and Tuscany
2 to 3 hours
Free Cancellation
5.0
(4)
from
$232
Per group
Immerse yourself in one of Tuscany's most celebrated wine regions—and enjoy a tour complete with a tutored tasting—on this two-in-one, small-group excursion. Led by your local guide, go for a vineyard walk, and learn more about the winemaking process on a behind-the-scenes cellar tour. Then, cap off your visit with a tasting of six premium wines, hosted on a terrace offering 360° views of Montepulciano.
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Montepulciano: Wine Tour and tasting
1 hour
Free Cancellation
3.7
(3)
from
$60
Once you have booked the tour, you will be able to go to the rental point to pick up your bikes and leave with the Virtual Guide, who will accompany the experience step by step. The tour is an easy and scenic loop of about 36 km, on dirt roads in good condition and short stretches of provincial road, avoiding the steepest variants. The first stops include the Church of San Biagio and a ride through cypresses and vineyards along Via della Montagna, to a beautiful viewpoint over the Val d’Orcia and Monte Amiata. The route continues with a scenic descent towards Monticchiello, between hairpin bends and rows of cypress trees, with a recommended stop in the village, near La Guardiola. The return crosses the Val d’Orcia again, with optional stops at Podere Il Casale and Capitoni/Fabbrica wineries. You then pass by Poggiano, with a view of Montepulciano, and with the possibility of a last stop at Caseificio Cugusi before returning.
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Montepulciano countryside E-bike virtual guided tour
3 to 4 hours
Free Cancellation
5.0
(6 Operators)
from
$90
Likely to Sell Out
An intimate and relaxing experience that begins with a tour of the winery and the cellar, followed by a tasting of 3 wines from our collection and of our Extra Virgin Olive Oil “Fattoria Svetoni”. A simple and pleasant way to understand our story and enjoy the classical tastes of Tuscany. One of the wines will be for sure the main of the region: Vino Nobile di Montepulciano DOCG, one of the most representative manifestations of Sangiovese grape variety. Known as "the King of Tuscany", together with Montepulciano "terroir", it creates elegance and complexity.
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Montepulciano Wine Tasting in the Tuscan Countryside
45 minutes
Free Cancellation
5.0
(6)
from
$29
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 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)
from
$231
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
(23)
from
$180
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)
from
$75
Discover the secrets to Tuscan cuisine during a small-group cooking class in Montepulciano. With the careful guidance of your host, learn how to prepare an appetizer, two types of fresh pasta with sauces, and an iconic dessert. Once everything is ready, sit down with your classmates and enjoy your handmade Italian feast. Afterward, you’re ready to impress your friends and family back home.
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Tuscan Cooking Class - Traditional 5 course menù
5 hours
Free Cancellation
4.9
(121)
from
$307
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
4.5
(9 Operators)
from
$266
Price varies by group size
Wander through the storybook charm of Montepulciano, where cobbled lanes echo with history and every corner hides a gem. Stroll along Gracciano Street lined with artisan boutiques, soak up sweeping views from Voltaia Belvedere, and feel the heartbeat of the city in lively Piazza Grande. Admire Renaissance masterpieces, uncover tales of civic pride at the Town Hall, and wrap up your journey deep underground in the majestic De’ Ricci wine cellars, where the region’s winemaking heritage comes alive. This walking tour is your gateway to the spirit, scenery, and flavor of Tuscany—one timeless step at a time.
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Montepulciano - Private Historic Walking Tour
2 hours
from
$463
Per group
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
4.0
(4)
from
$353
Price varies by group size
"Here is Volterra!", says Alice Cullen on board of the yellow Porsche, as soon as she sees the Tuscan village, seat of the Volturi. Actually, that village with narrow streets that go uphill is Montepulciano. You will discover the Italian film set of "New Moon - Twilight Saga", accompanying you on a visit to the more or less known sites of the town, which have been the setting of some overwhelming scenes of the film.
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Twilight Saga: the New Moon tour in Montepulciano
2 hours 30 minutes
Free Cancellation
3.5
(4)
from
$138
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)
from
$151
Price varies by group size
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)
from
$156
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
4.7
(15)
from
$58
Discover Montepulciano with a private tour. In 1500 Antonio da Sangallo fortified this town, an ancient settlement of Etruscan origin, which became the important castle on the borders of the Grand Duchy of Tuscany. Montepulciano was the birthplace of Poliziano, poet and secretary of Lorenzo the Magnificent and we will pass under his house. The elegant town is full of noble residences and Renaissance churches. we will visit the Piazza Grande, the natural theater of many artistic, folkloric and oenological events. We will visit its incredible medieval cellars dug into the rock under the noble palaces, for centuries the place of aging of Vino Nobile di Montepulciano DOCG. Let's discover together the surprising beauties of this small city of art - It is also possible to go on an exciting URBAN TREKKING from San Biagio to Porta a Prato and back, with a visit to the medieval cellars. Suggested tour for ART and WINE lovers
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Montepulciano private guided tour
2 hours
Free Cancellation
5.0
(23 Operators)
from
$324
Per group
This tour is designed for travelers who want to experience Tuscany authentically yet effortlessly: we ride on quiet, scenic backroads away from the classic tourist tracks. The experience is completely private and customizable, guided by a passionate local expert who knows every hidden corner of the Val d’Orcia. The e-bikes make it easy for everyone to enjoy postcard-perfect landscapes in Montepulciano. It’s the perfect blend of nature, culture, and relaxation!
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Montepulciano Mountain Bike Private Tour
3 hours
Free Cancellation
4.5
(9 Operators)
from
$156
Price varies by group size
Likely to Sell Out
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)
from
$139
Price varies by group size
Magnificent experience in the beautiful Tuscan hills. You will spend a few hours immersed in the Tuscan countryside transported on a vintage Fiat 500 from 1970. You will be able to photograph the streets and the beautiful landscapes that will accompany us on the tour that I offer you. We will start from the Temple of San Biagio and then head to Monticchiello, a typical Tuscan village surrounded by hills. From Monticchiello we will go to Pienza, a village perched on a hill where you can admire the landscapes of the Val d'Orcia. We will make stops along the tour where you can take photos that will best remember your vacation. From Pienza we will return to the Temple of San Biagio. We will stop to admire and photograph the 16th century Temple of San Biagio, the medieval village of Monticchiello, famous for its curves and cypresses, the Elysian Fields Pienza Famous for the final scene of the film Gladiator.
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Private Tour in Vintage Fiat 500 - Val d'Orcia
3 to 4 hours
Free Cancellation
3.0
(2)
from
$348
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