Top Montepulciano Sightseeing Tours

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.

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.

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. During our tour, we will climb through 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? When we reach the summit of the town, we will find ourselves in the magical Piazza Grande, where we will be able to visit the never-finished Cathedral, the Fortress, and enjoy a wonderful view over the Val di Chiana and part of the Val d'Orcia. Last but not least, our tour will take us underground to visit one of the ancient wineries of the town, and taste a glass 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. (Anti-Covid Vaccinated Tour Guide)

This tour will be a slow one, giving you the opportunity to decide if you wanna stop for an unplanned visit or, just to get a taste of the typical food and/or wine offered along the way, getting the opportunity to save time and to discover the best corners and to get the shots of the medieval town... how can you miss it?

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.

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.

Immerse yourself in an unforgettable culinary journey through the picturesque hills of Val d'Orcia and Val di Chiana, where the charm of art, history, and nature converges in a perfect dance. Join us for a "Food and Wine" experience that will awaken your senses and transport you to a world of sensory delights. Begin your journey in the heart of Montepulciano, a Renaissance gem nestled among lush hills... or we can start from the countryside and the farm, depending from your arrival! Explore historic cellars where the famous Vino Nobile di Montepulciano comes to life. Taste the secrets preserved in oak barrels and discover the mastery of local winemakers. Savor delicious local products, from extra virgin olive oil to cheese and cold cuts specialties that embody the authentic taste of the region. This is not just a tour; but a total immersion into the art of fine dining and wine culture. Experience the history in the vineyards, and the joy in savoring authenticity in every sip.

While the Tuscan countryside is enchanting from any angle, the beautiful landscape is truly breathtaking from the air! Get an amazing new perspective on the area’s vineyards, olive groves, and rolling hills with a morning hot air balloon flight. Climb into a basket and rise up into the air for an unforgettable flight over Montepulciano and Val d'Orcia. Once back on solid ground, celebrate with a glass of Champagne and a light breakfast.

This unique experience allows you to visit the most interesting places in Val d'Orcia and Montepulciano crossing country roads to admire nature and works. The departure begins and ends in my Fattoria Madonna della Querce, next to the Sanctuary of the Madonna della Querce in Montepulciano. Here I breed Cinta Senese pigs, a type of black pig with a white belt, of Tuscan origins and very ancient. We will take a short walk among the olive trees and the vineyard to get to the pigs, which are free, separated by an electric fence. We can walk with them, touch them and take pictures. Lunch is included in the experience and includes a menu with: Bruschetta, ribollita in winter and panzanella in summer, platter with our cured meats, pecorino di Pienza cheeses with jams, cantucci and vinsanto, water, house wine, espresso coffee.

Embark on a captivating journey through the Tuscan Countryside, immersing yourself in the timeless beauty of this renowned region, celebrated for picturesque landscapes, historic towns, and exquisite wines. Our adventure begins in Montepulciano, a charming hilltop town renowned for medieval architecture and delectable wines. Explore cobblestone streets, visit historic cellars, and savor the rich flavors that make Montepulciano a haven for wine enthusiasts. Next, venture to Pienza, a UNESCO World Heritage site and birthplace of Pope Pius II. Marvel at well-preserved Renaissance architecture, stroll quaint streets, and indulge in local pecorino cheese—a culinary delight for which Pienza is renowned. Continuing the journey, arrive in Montalcino, a fortress town surrounded by vineyards producing the illustrious Brunello di Montalcino wine. Delight your senses with a wine tasting experience, sampling bold and complex flavors that have made this wine world-famous.

The Italian Lifestyle is a sense of life that you can feel only here, in Italy and especially in Tuscany! The experiece includes a delightful tasting of sweet and savory pastries with a creamy Cappuccino before to reach the main square for a really unique wine tasting of Nobile and Rosso di Montepulciano. Your lunch in a typical Fattoria or Trattoria with drinks and... last but not least: the guided visit of an organic farm in the afternoon, to enjoy the demostration of the Pecorino cheese production in their own cheese factory. Visit of the farm and, at the end, we'll be delighted by the tasting of their products, including their wine. This tour is totally customizable for the reasons I've already written... feel free to ask me to personalize your "A day in Tuscany".

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

Explore Quaint Villages and Timeless Landscapes Our journey will take you off the beaten path, winding through both lesser-known hamlets and iconic landmarks alike. Immerse yourself in the rich history and culture of each village we visit, from hidden gems tucked away in the countryside to well-known destinations steeped in tradition. Capture Every Moment, Embrace Every View As we traverse the rolling hills and winding roads, there will be ample opportunities to pause and soak in the panoramic views. Experience the Joy of Open-Air Travel Feel the sun on your face as you cruise through the Val d'Orcia on your Vespa. This isn't just a tour – it's an immersive journey into the heart of Tuscany's natural beauty. Let the open road be your guide as you embrace the freedom of outdoor exploration. Don't Miss Out on This Unforgettable Experience Join us for a Vespa adventure like no other and discover the magic of Val d'Orcia in a whole new way.