Florence to Arezzo

Take a break from Florence’s museums and escape to a trio of the most charming towns in Tuscany’s UNESCO-listed Val d’Orcia region. Taste prized red wine varietals like Nobile di Montepulciano and Brunello di Montalcino, stroll through medieval squares in Pienza, and sample authentic Tuscan fare on this all-inclusive tour that takes the planning and guesswork out of a day in wine country.

Take a day trip to Assisi and Cortona and discover these charming hilltop towns alongside a guide. Departing from Florence, travel first to Assisi, where you visit the Convent of Santa Chiara, the Basilica of San Francesco, and hear about the life of St. Francis of Assisi. Pause for a peek inside Santa Maria degli Angeli church, believed to be a favorite spot of St. Francis. Then head to Cortona for some time to explore independently before returning to Florence.

Discover some of the highlights of Tuscany on this day trip from Florence by coach. Visit historical hill towns Pienza, Montalcino, and Montepulciano; admire the gorgeous, vineyard-covered scenery of Orcia Valley (Val d’Orcia); and enjoy cheese and wine tastings as you stop at local wineries and other venues. It’s a great day out in the Italian countryside.

Journey to the origins some of Italy’s most celebrated ‘vino’ on a private, full-day tour designed for wine lovers and connoisseurs. Visit the medieval town of Montalcino for a gourmet lunch and tasting of famed Brunello di Montalcino wine. Continue through Tuscany’s World Heritage-listed Val d’Orcia region to reach Montepulciano, known for its Nobile di Montepulciano wine, and taste this prized elixir at a winery. Learn about the area’s history and winemaking heritage from a private guide, and meet local producers for an immersive tasting experience. Price is per group, with a maximum of either three or eight passengers, depending on season and vehicle type.

Discover Assisi and Cortona on a day trip from Florence, and make the most of a private driver, just for your group. First, travel to the pilgrimage town of Assisi to walk in the footsteps of St. Francis, Italy’s patron saint. Learn about his life in the town, and visit the basilicas of St. Francis and St. Claire. After a break for lunch, continue to Cortona for some sightseeing at your leisure. Entrance fees and food are at your own expense.

Experience the sights and flavors of Tuscany on a full-day tour from Florence that takes you through the Val d'Orcia region to the elegant Renaissance architecture of Montepulciano. Explore the history of Montalcino’s imposing fortress and the jewel-box village of Pienza, savoring the bounty of the Val d’Orcia region with tastings of local wines and specialty foods along the way.

Home to medieval hilltop towns and fertile vineyards, Tuscany is widely considered the jewel in Italy’s crown. On this tour, visit the beautiful Tuscan towns of Pienza and Montepulciano, and enjoy a complete immersion in authentic Italian culture and cuisine. With travel from your Chianti, Florence, or Siena hotel, sample local wines in historic cellars and savor a delicious lunch in a traditional Montepulciano winery.

Tuscany is one of the most popular regions in Italy, beloved for its rolling countryside, charming villages, and unforgettable cuisine. With this three-day tour, sample the best of all three without having to puzzle out the complicated travel logistics. Explore the delightful medieval centers of San Gimignano and Siena; sample wines, extra-virgin olive oils, and other delicacies in Chianti; and relax in the natural hot springs in the Val d’Orcia.

Discover Tuscany’s renowned wine country on a day trip from Florence with a small group. Led by a driver-tour escort, venture to the town of Montepulciano by minivan and stop at a rustic wine cellar to taste the area’s vino di nobile blends. Then head to Montalcino area to sample three Brunello di Montalcino wines. Top off your day with a stroll to Pienza, a beautiful Renaissance hill town and home to the famous Pienza Pecorino cheese. Numbers are limited to eight people to keep this experience as intimate as possible.

Explore the scenery and culture of the Tuscan countryside on this guided all-day adventure. After meeting your guide in Florence, travel with a friendly, informative guide to the towns of Siena, Montepulciano, and Cortona. Marvel at charming medieval squares, see where the vampires of the Twilight Saga’s New Moon converge, enjoy a complimentary wine tasting in a historic cellar, and savor a delicious lunch surrounded by rolling hills.

With ancient vineyards, Renaissance architecture, and colorful local culture, the UNESCO–listed Val d'Orcia is considered among Tuscany’s must-see attractions—but arranging travel independently from Florence is a challenge. With this tour, begin at your Florence hotel and head into the Tuscan countryside by comfortable minivan with your guide. Reach the ancient settlements of Montepulciano and Pienza with ease, and admire beautiful vineyard views in Montalcino.

Taste your way through some of Tuscany’s finest wine regions and most charming medieval villages on this private, full-day tour from Florence. Drive through the scenic Orcia Valley and visit the birthplaces of prized Brunello di Montalcino and Nobile di Montepulciano red wines. Whether you want to explore the medieval villages, tour historic wine cellars and vineyards or savor a farm-fresh lunch, a private driver and guide will customize the itinerary to create a perfect day in the Tuscan countryside. Price is per group, based on a maximum of 7 passengers per vehicle.

Spend a day in the UNESCO-listed Val d'Orcia on this 10-hour private tour from Florence. Visit Montepulciano and Pienza to admire the historic architecture. Sample some of the area's famous Noble Wines.

Indulge in wine tasting and vineyard tours in the Montalcino area, stopping at two different wineries, on this full-day tour from Florence. No need to rent a car or assign someone to be a sober driver; all transportation is provided out of Florence and between the wineries. Stop at two wineries to learn about their methods and taste Brunello wines, then explore the UNESCO-listed Val d'Orcia with engaging narrative from your guide.

Travel through the Val d'Orcia region of Tuscany with the benefit of your own private guide on this full-day tour from Florence. Receive personalized attention as you visit picturesque towns including Montepulciano, Pienza, and Montalcino. Stop into a winery, go wine tasting, and stroll through streets lined with centuries-old buildings in a region that has been designated a UNESCO World Heritage Site.

Experience the heart of Tuscany by visiting the enchanting Val D’Orcia led by your private driver. Let your personal chauffeur do all the work and take you on a journey through the spellbinding Val D'Orcia countryside, a region known for its scenic beauty, picturesque villages, rolling hills and cypresses! Explore in total freedom the enchanting towns of Montalcino, Pienza and Montepulciano and savour the best wines in the world! The first stop will be Montalcino, land of the world-renowned Brunello wine, a labyrinth of cobbled streets, quaint wine shops and Romanesque-style churches. The following stop is Pienza, which stands high upon a hill and dominates all the Orcia valley with extraordinary views. The last stop reaches Montepulciano, home to the famous Vino Nobile vineyards and more recently famous for the filming of the vampire movie "New Moon". Enjoy your free time in the most elegant village of the entire Val D'Orcia.

Travel through the Tuscan countryside with a private driver on this day trip to Assisi and Perugia. Departing from Florence, explore the medieval city of Passignano sul Trasimeno and enjoy views of the beautiful Lake Trasimeno. Then head to Perugia to see where Renaissance artist Raphael worked, before exploring the town of Assisi, once home to Italy's patron saint. While there, admire the UNESCO-listed Basilica of St. Francis.

Discover the natural beauty of Italy's Val d'Orcia on this private tour that introduces you to the postcard-perfect scenery of rolling hills and vineyards. You'll visit the towns of Montepulciano, Pienza, and Montalcino; tour a winery; and enjoy included wine tastings and a Tuscan lunch for a well-rounded experience in this UNESCO World Heritage–listed valley.

Discover the medieval Tuscan hill towns of Cortona and Montepulciano, without the hassle of spending hours on trains or busses. Enjoy the luxury of a private, chauffeured drive through the Arno Valley. Explore the impressive sights and historic attractions of Cortona, then eat a light lunch before strolling through the charming streets of Montepulciano. Your guide suggests the best places to stop, and customizes the tour to your interests.

Take a break from the crowds of Florence and discover Arezzo and Cortona on a private 9-hour. All-inclusive private transportation from your hotel allows you to comfortably see a long list of attractions in a short amount of time. Visit historical sites, including the 9th-century Etruscan Atrium, as well as filming locations for “Life is Beautiful” and “Under the Tuscan Sun”. Enjoy ample free time to explore both Tuscan towns.

Delve into Tuscany’s history and culture on a full-day private tour of Siena, Montalcino and Val d’Orcia. Depart early from Florence to take your time as you visit lovely towns, see stunning architecture, savor delicious food and wine, and learn about the places you visit from your informative driver-guide. In the Val d’Orcia region, you can enjoy the ambiance of towns such Pienza or Montepulciano. Your driver-guide customizes the tour itinerary to best suit your interests.

Experience the world-famous wine and scenery of Tuscany on this full-day tasting tour from Florence. Travel along ancient roads through a landscape of vineyards and olive groves, stopping at the charming village of Montalcino, located in the renowned Brunello wine region. Learn about the origins and characteristics of Brunello wine with a cellar tour and tastings at two different wineries, and savor regional cuisine with a traditional Tuscan lunch. 

Visit three of the most captivating towns in Tuscany in a single day with this tour that includes time-saving transportation directly from Florence. Enjoy a guided tour of Siena to take in the Piazza del Campo and Duomo, then relax over a traditional Tuscan lunch with wine at a local cellar. Spend your afternoon exploring first San Gimignano and then Pisa—including the iconic Leaning Tower—at your own pace.

Enjoy a relaxing shopping spree with this private 4-hour trip to the Montevarchi Prada Outlet. Enjoy the convenience of a personal driver who frees you from the hassle of parcels and purchases. Continue to the prestigious The Mall near Reggello to browse 22 boutiques of clothing, accessories and high quality jewelry if you are not satisfied.