Top Montepulciano Tours, Sightseeing & Cruises

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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!

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.

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.

Slow down and explore the stunning Tuscan hills of the Val d'Orcia and Valdichiana far from the urban crowds and chaos with this scenic horseback riding excursion just outside of Montepulciano. Meet your riding guide and amble through the vineyard-covered hills on horseback, stopping to snap photos and take in the view. Then relax over an alfresco picnic featuring local Tuscan specialties.

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.

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.

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.

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.

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.

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

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.

Combine a scenic, gently-paced cycling ride with a tasty lunch and wine tasting during this half-day, small-group excursion in Tuscany. Bike through winding country rodes and picturesque villages. Then, taste local wines in a vineyard and enjoy a Tuscan lunch. Upgrade to an e-bike at an additional cost.