Day Trips from Tuscany to Montalcino

Explore rolling hills, sunflower fields, and cypress-lined roads in Tuscany, savoring two local treasures: red wine and Pecorino cheese. Begin in Pienza, a Renaissance gem in Val D’Orcia, with a tasting of its famed Pecorino cheese at a traditional “bottega.” Next, visit Montalcino, home of world-renowned Brunello wine. Enjoy a private winery tour, a cellar visit, and a Tuscan lunch perfectly paired with Brunello wines to cap off your culinary journey.

Explore the Tuscan countryside on this full-day outing to the Italian countryside from Florence to discover the region's wine-making culture. Visit the medieval hill town of Montalcino for a stroll through its streets. Then, continue to Montepulciano—which is famous for the variety of grapes that bear its name—for a wine tasting and a visit to the underground city. On the return journey, drive through the UNESCO-listed Val d’Orcia and make a couple of panoramic stops.

Take a day excursion to San Gimignano, Chianti, and Montalcino to experience the charm of the Tuscan countryside. Savor the best local blends during a wine tasting at a renowned Chianti winery. Optional lunch for an authentic gastronomic experience. Begin your full-day journey by seeing San Gimignano, well known as the City of Fine Towers. With your tour guide's insights, take advantage of your free time to explore the historical center and its artisan stores. Explore the birthplace of Vernaccia, the renowned white wine that is regarded as Italy's first DOCG wine, after that. Enjoy a sample of Chianti and you can choose to buy the optional lunch at a nearby winery. Discover the UNESCO World Heritage Site of Val d'Orcia before continuing on to Montalcino, which is famous for its panoramic vistas of Brunello grapes. Finish your tour by visiting a local wine cellar to experience the renowned Brunello di Montalcino.

Pienza and Montalcino are top foodie destinations, but getting there by train and bus can eat hours out of your day. Experience the area's top cheese and wine with ease on this private tour from Siena. Admire the Val d’Orcia scenery, learn about cheese making during an organic dairy farm tour, visit the World Heritage–listed town of Pienza, and enjoy tastings of the region’s renowned Brunello wine at a Montalcino winery.

Embark on an unforgettable journey through Tuscany and discover historic cities, cinematic landscapes, and world-famous wines. Departing from Florence, explore enchanting destinations such as Cortona, Montepulciano, and Montalcino, immersing yourself in the region's unique culture, architecture, and flavors. In addition to the experience during the trip, you will also receive an exclusive ebook to complement your journey and make your discoveries even more special. The material includes historical curiosities, references to films shot in Tuscany, information about the famous local wines, cultural tips, and details about each destination visited. A perfect guide to deepen your connection with the Italian essence before, during, and after the experience.

Tour with a certified sommelier guide expert on Brunello. Discover Tuscany with local expert out of beaten path. learn the history of Brunello wine making and visit historical wineries.

The tour is provided and focused to give you the best, during the driving, the driver is prepared and trained to provide description on Hystory and places reached, and ready to answer to your questions. It's an immersive cultural experience , inside knowledge and memorable encounters with local traditions. Full assistance during the trip is also provided. Changments on itinerary are also avalaible. Believe it or not, the Val d'Orcia experience is both relaxing and exciting!

Discover the charm of Montalcino and the Val d'Orcia on a full day e-bike tour with a local Guide who knows the territory like the back of his hand. Ride among the most beautiful dirt roads in the world in a Unesco heritage area. You will ride about 45 - 50 km through the low-traffic roads of the Tuscan hills, while a certified Guide will share with you the history and secrets of the territory. You will stop at a historic winery to taste the renowned Brunello di Montalcino and the oil produced by the company, accompanied by a delicious platter of local cold cuts and cheeses. You will admire the Romanesque Abbey of Sant'Antimo before returning to Montalcino, making your trip an unforgettable experience. - E-bike tour of about 5 hours with departure and return to Montalcino - Certified Guide available for assistance and information - Tasting of 3 Brunello wines with cold cuts and cheeses - Panoramic routes between dirt and paved roads of the Val d'Orcia

Take a break from the crowds in Siena, and spend an afternoon in the wine town of Montalcino on this group tour. Don't worry about hiring a car to get there, with transportation all sorted. Learn about Brunello di Montalcino wine and its production, along with wine tastings paired with local snacks. Admire views of the Tuscan countryside from this hill town as you discover the region’s generations-old winemaking traditions.

Avoid the hassle of planning routes between scattered wine towns and booking separate tastings on your own with a guided day trip from Siena. This experience connects the flavors of Montepulciano and Pienza with the scenic landscapes of Val d'Orcia, letting you move easily between villages without logistics stress. Spend your time enjoying wine, local food, and countryside views at a relaxed pace.

Tuscany is Italy’s gastronomic heart and this full-day tour from San Gimignano is the ideal introduction for traveling foodies. Sample regional wines and Tuscan specialties at a Montalcino winery; enjoy a self-guided tour of Montalcino fortress; taste regional delicacies such as Pecorino cheese in Pienza; and discover the famous Nobile di Montepulciano wine at a Montepulciano winery.

Experience the sights and flavors of Tuscany on a full-day tour from Florence that takes you through the Val d'Orcia region to three historic villages. Admire the elegant Renaissance architecture, explore the village of Pienza independently, and savor the bounty of the region with tastings of local wines in Montepulciano.

Escape Florence for a day and discover the beauty of Tuscany on a journey through the famous Val d’Orcia, one of Italy’s most iconic regions. Travel by air-conditioned GT coach with an expert multilingual tour leader and admire rolling hills, vineyards, olive groves, cypress-lined roads, and medieval villages. Visit Montepulciano and enjoy free time to explore its Renaissance center, picturesque streets, artisan shops, and panoramic views. Continue with a traditional Tuscan lunch and wine tasting in Val d’Orcia, featuring local wines including Rosso di Montepulciano and Vino Nobile di Montepulciano. Then discover Pienza, renowned for its Renaissance charm, before continuing to Montalcino, famous for its prestigious wines and medieval atmosphere. Experience the authentic flavors, landscapes, and traditions of Tuscany before returning to Florence in the evening.

Save time planning your perfect Tuscan outing with this full-day guided tour to Val d’Orcia from Florence. Travel through the picturesque countryside in your comfortable coach and discover the enchanting towns of Pienza and Montalcino. You’ll explore the interactive Temple of Brunello museum before sitting down to a delicious gourmet lunch paired with three glasses of local wine.

Knowing where to visit in the Tuscan countryside can be daunting for first-timers, especially if you're starting off in Florence. Simplify your day out with this group tour. Once you've boarded your coach, sit back knowing the transportation and activities are covered, meaning you can fully immerse yourself in the experience. Enjoy visiting Pienza, Montalcino, and Montepulciano, the Orcia Valley, and taking part in a wine and cheese tasting.

Experience the highlights of southern Tuscany on a full-day tour from Siena through the rolling landscapes of the Val d’Orcia. Travel in comfort and enjoy a perfect blend of food, wine, history, and scenery. Your first stop is Montepulciano, where you’ll enjoy an authentic Tuscan lunch featuring local cured meats and cheeses, followed by handmade Pici pasta with ragù, or tomato sauce for vegetarian guests. During lunch, take part in a guided tasting of Rosso di Montepulciano and the renowned Nobile di Montepulciano, perfectly paired with the regional cuisine. Continue to Pienza, the “ideal Renaissance city,” and enjoy free time to stroll its picturesque streets, admire panoramic countryside views, and browse artisan food shops. In the afternoon, reach Montalcino, home of the prestigious Brunello di Montalcino. Visit a local winery for a guided tasting and learn about the traditions and aging process behind one of Italy’s most celebrated wines.

Experience the highlights of southern Tuscany on a full-day small group tour from Florence through the rolling landscapes of the Val d’Orcia. Travel in comfort and enjoy a perfect blend of food, wine, history, and scenery. Your first stop is Montepulciano, where you’ll enjoy an authentic Tuscan lunch featuring local cured meats and cheeses, followed by handmade Pici pasta with ragù, or tomato sauce for vegetarian guests. During lunch, take part in a guided tasting of Rosso di Montepulciano and the renowned Nobile di Montepulciano, perfectly paired with the regional cuisine. Continue to Pienza, the “ideal Renaissance city,” and enjoy free time to stroll its picturesque streets, admire panoramic countryside views, and browse artisan food shops. In the afternoon, reach Montalcino, home of the prestigious Brunello di Montalcino. Visit a local winery for a guided tasting and learn about the traditions and aging process behind one of Italy’s most celebrated wines.

Benefit from a private full-day tour of Tuscany with round-trip transportation from your accommodation. Have free time during your visits to Montalcino, Pienza, and Montepulciano, and have the option to stop for lunch, and wine or cheese tastings in the countryside. Travel in comfort in an air-conditioned private vehicle with hotel pickup and drop-off included.

Pedal through the Tuscan countryside during this half-day e-bike tour through Brunello. Bike along unpaved roads with ease on your electric bike towards local Tuscan vineyards. Enjoy a wine tasting at the Abbey of Sant’Antimo and learn about the ancient winemaking process. Sample three glasses of wines, including the Brunello di Montalcino, before heading to the medieval town of Montalcino to explore.

Tuscany produces one of Italy’s flagship wines: Brunello di Montalcino. Exploring the countryside where these wines are produced, however, means navigating confusing rural roads and searching for remote wineries. With this wine tour, leave the hassle of driving to the experts and instead enjoy a stress-free day of wine tasting and sightseeing. Visit two winereis and a cellar.

Experience medieval Tuscany on a group day trip. Visit the fortified town of Monteriggioni with tickets to its Templar Museum and access to its medieval walls. Continue on to the UNESCO heritage area of Val d'Orcia and stop at the medieval village of Montalcino for an optional taste of local wine and nibbles. Finish your tour with a wander through Pienza before the scenic drive back to Florence.

This private tour is designed to offer an authentic experience with maximum comfort and local insight. It starts directly from your hotel in a fully licensed Mercedes van with air conditioning for a smooth and relaxing ride. Accompanied by a professional driver-guide-certified sommelier, fluent in English and Italian born and raised in the Montalcino area. Travel through the stunning Val d’Orcia admired worldwide for its rolling hills and iconic landscapes. The highlight of the tour is an exclusive visit to a family-owned, organic Brunello winery, where you will walk through the vineyards, tour the cellars, and enjoy a guided tasting of selected red wines, including the celebrated Brunello di Montalcino, accompanied by a tasting extra virgin olive oil. The experience concludes with free time in the medieval town of Montalcino, the heart of the Brunello wine region, where you can explore historic streets, admire monuments, and browse charming local shops at your own pace.

One of the best wine region of the world with a local driving-guide and wine connoisseur, born and raise in the area.Private tour in two boutique wineries , driving through the most scenic road of Val d'Orcia with chance to stop for the best Tuscan countryside pictures.

Departing from Florence, enjoy a scenic drive through the Tuscan hills before reaching Trequanda, a charming medieval village in the Val di Chiana. Here, you can explore the Rocca di Trequanda, a well-preserved fortress with Ghibelline battlements, and the nearby Church of Saints Peter and Andrew, known for its stone&brick façade. The highlight of the stop is a visit to a local farm, where you’ll learn the techniques behind creating a Supertuscan wine. You’ll even blend and label your own bottle, becoming a winemaker for a day and taking home a unique souvenir. The journey continues to Montalcino, famous for its prestigious Brunello wine. Enjoy views over the Val d’Orcia, visit the impressive Montalcino Fortress, and stroll through Piazza del Popolo. A short distance away stands the beautiful Abbey of Sant’Antimo, an excellent example of Romanesque architecture. Your day concludes at a local winery with a guided tour and a Brunello tasting, celebrating an authentic flavor of Tuscany.