Day Trips from Tuscany to Val d'Orcia

Escape Florence for a full-day journey through the heart of Tuscany’s Val d’Orcia, a UNESCO World Heritage landscape of rolling hills, vineyards, olive groves, and cypress-lined country roads. Visit three of the region’s most beautiful towns, Montalcino, Pienza, and Montepulciano, each known for its history, views, and authentic Tuscan character. Begin in Montalcino, home of the world-famous Brunello wine, where you’ll visit a wine cellar and enjoy a tasting. Continue to Pienza, the Renaissance “ideal city,” famous for its architecture, panoramic views, and Pecorino cheese. Finally, explore Montepulciano, renowned for Vino Nobile, and enjoy another wine and Pecorino tasting inside a historic underground cellar before returning to Florence.

Trace the historic Via Francigena pilgrim route by e-bike, taking in some of the most charming hilltowns in Tuscany along the way. Begin your adventure with a walking tour of Siena before heading out with your guide to pedal through the Tuscan countryside. Stop to admire the medieval villages of Monteriggioni and San Gimignano before heading back to Siena.

This customized day trip pairs the otherworldly landscapes of southern Tuscany with the region’s frozen-in-time villages and prized flavors. Relax and take in the views from a luxury vehicle while a private guide and driver handles the country roads. Taste famed Brunello wine in Montalcino and Pecorino cheese in lovely Pienza, visit a medieval monastery, and get hand-picked recommendations for an authentic Tuscan lunch.

Explore southern Tuscany with your own private guide on a full-day wine and food tour from Siena. Visit Pienza, Val d'Orcia, Montalcino, and more as you take in small towns, a 14th-century monastery, and sample Brunello di Montalcino, the famous wine of the region. Ride in comfort in a luxury vehicle with a private guide who shares the best of the region.

Take a break in the countryside with a private tour that includes visits to boutique wineries and a sustainable, family run cheese farm. Enjoy a full day dedicated to wine and cheese, exploring the heart of Tuscany. Drive through the Val d'Orcia, a UNESCO World Heritage Site, and savor some of the region’s finest red wines, including Vino Nobile di Montepulciano and Brunello di Montalcino. Stroll through the medieval squares of Pienza and sample authentic Tuscan cheeses at a historic estate, featuring one of the most breathtaking terraces overlooking the Orcia Valley.

Slow down and experience Tuscany at your own pace in this refined side of Tuscany with a private Val d’Orcia slow experience, designed for those who value beauty, comfort, and unhurried moments. No rushing, no tight schedules—just time to enjoy Tuscany. Begin with a traditional Italian breakfast in the quiet village of Monticchiello, featuring homemade pastries and freshly brewed coffee. Travel through the iconic rolling hills of the Val d’Orcia, stopping in elegant villages such as San Quirico d’Orcia, far from the crowds. Enjoy a curated Tuscan picnic in nature with artisanal cheeses, cured meats, fresh bread, and your choice of wine, beer, or water—set against one of Italy’s most breathtaking landscapes. In Bagno Vignoni, take time to explore or simply unwind. Relax under the trees and experience a peaceful siesta in complete tranquility. * Private, refined slow tour * Italian breakfast and curated picnic * Scenic villages and countryside * Time to relax and disconnect

Get a taste of Tuscan landscape, wine, and food on this full-day private tour from Florence. Led by an English-speaking driver, discover the regions of Chianti and Val d’Orcia, soaking up the local flavor with several wine tastings. Explore the charming towns of Castellina and Montepulciano, and savor a traditional Tuscan lunch at a farmhouse in Montalcino.

Discover Tuscany's most iconic hilltop gems on this full-day excursion from Florence. Organizing a trip to the region’s scattered medieval villages can be challenging without local insight or a grasp of the Italian language. This group experience covers the logistics, so you can spend your time basking in the beauty of Val d'Orcia, sipping wine at a rural vineyard, and exploring medieval fortresses along the way.

Visit two of Tuscany's beautiful hilltop towns, plus enjoy tours and tastings at boutique wineries in Chianti and Montalcino on this small-group tour from Siena. All transport is included for a hassle-free experience, with free time to explore Pienza. Sample top Chianti, Brunello, and Super Tuscan wines, and relax over a Tuscan lunch featuring local specialties.

Discover the history of the Chianti region, visit Montalcino's medieval fortress, and enjoy a scenic drive through Val d'Orcia on this small-group tour from Siena. Taste Chianti Classico and Brunello wines paired with Pecorino cheese, bruschetta, salame, and extra virgin olive oil. Explore the historic cellar and learn about the wine production process in a boutique family-owned winery.

Cross the Tuscan hills in search of fine wine, local food, and unforgettable views. This small group tour from Florence takes in UNESCO heritage sites, charming medieval towns, and a landscape that captivated Renaissance painters. Stop in Montalcino for a lunch of local fare and a tasting of some of the best wines in the world. And head to Montepulciano to wander its picturesque palazzos and visit the historical wine cellars.

Discover the essence of Tuscany on the Brunello di Montalcino Wine Tour, a full-day adventure through Val d’Orcia. Marvel at rolling hills and cypress trees as you visit a boutique winery for an organic Brunello tasting, learning about the winemaking process directly from passionate artisans. Enjoy a farm-to-table lunch featuring local ingredients, and explore charming hilltop villages like Pienza or Monticchiello. This tour is designed for wine enthusiasts seeking authentic experiences, all within a picturesque setting. - Full-day tour lasting 10 hours through the stunning Val d'Orcia region - Taste organic Brunello wines at a family-owned boutique winery - Enjoy a delicious farm-to-table lunch with sweeping valley views - Explore quaint hilltop towns for an intimate glimpse of local life

Experience the essence of Tuscany on this immersive Brunello tour through Val d’Orcia. This tour is specially crafted for Brunello enthusiasts and curious wine lovers eager to experience the elegance and rich story behind Tuscany’s most iconic red. This tour offers much more than wine tasting — it is a celebration of Tuscany’s landscape, heritage, and the passionate people who bring Brunello di Montalcino to life.

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.

Sip wine and go back to medieval times during this small-group guided tour that includes an authentic Tuscan lunch. Wander the streets of the ancient, hilltop town of Montalcino known for its wine before touring the Brunello di Montalcino winery. Learn how biodynamic wines are made and sample varieties straight from the barrel. After lunch, visit a second winery to sip samples and eat Tuscan fare.

Join this full-day sensory-filled journey through Val d'Orcia with exquisite wine and cheese tastings. Spend your day immersed in Tuscany's charming medieval towns while enjoying the world-renowned Nobile di Montepulciano and award-winning Pecorino di Pienza. And don't forget about the lunch and refreshing alcoholic beverages included. All these wonderful experiences will take place in a comfortable air-conditioned vehicle. It's a full-day adventure you won't want to miss.

Ride through the rolling hills of Pienza’s countryside on a private e-bike experience, discovering charming landscapes and historic villages. After the ride, step by step, visit a working mill where your guide will show the journey from wheat to fresh pasta, sharing local stories, traditions, and insights into Tuscan culture, wine, gastronomy, and the region’s vineyards. Glide through vineyards and golden fields in the heart of UNESCO-listed Val d’Orcia, near Montalcino, enjoying cinematic views, iconic cypress-lined roads, and hidden gems beyond usual sights. With TREK e-bikes and carefully chosen routes, the journey unfolds at a relaxed pace, letting you explore far from crowds. The tour concludes with a light Tuscan lunch in a special setting beside a castle, offering a final gastronomic moment highlighting the region’s culture, flavors, beauty, and local craftsmanship — an immersive Tuscan journey for travelers seeking authenticity, refinement, and true Tuscan elegance.

Discover Tuscany's stunning landscape, culinary delights, and UNESCO-listed sites on a day trip to Montepulciano and Pienza from Siena. Avoid the hassle of driving yourself and be led by a local guide. Admire the architectural gems of the Val d'Orcia region and stop at a dairy farm for lunch and samples of salty Pecorino cheese. Conclude your trip in the scenic hill town of Montepulciano, with a visit to a winery.

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.

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.

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.

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.