The Tuscan landscape — abundant in luscious olive groves and iconic cypress trees — is a beloved destination for food and wine lovers, those in perpetual pursuit of la dolce vita. While summer travel is popular in the region, an off-season visit delivers a unique perspective on Tuscany. Autumn offers milder temperatures and quieter streets and destinations — thanks to smaller crowds — letting you leisurely explore at your own pace. Book your travel to Tuscany this fall and experience old-world charm infused with modern luxury, all set against rolling hills, towering mountainscapes, and the Tyrrhenian Sea coastline. From the moment you say ciao until it’s time to bid arrivederci, we’ll help you plan an unforgettable off-season Tuscan trip. 

Take Advantage of the Off-Season

Why visit Tuscany in the fall? Milder weather makes it easy to explore all day long with balmy breezes and inviting temperatures. The change in season doesn’t affect the waters of the Tyrrhenian Sea, which stays gloriously warm well into October. From June to August, the streets are lined with tourists and travelers, while the off-season sees fewer crowds on the roads and at major attractions. And, even though the locals are returning to their normal pace, there’s still plenty to do and see, ensuring you get the full Tuscan experience.

Where to Go and What to See in Tuscany?

There’s no singular way to experience Tuscany, giving you seemingly endless options for your Italian vacation. There is a collection of distinct cities and charming towns within the area, which stretches from the Tyrrhenian Sea in the West to Umbria in the east, Lazio in the south, and Emilia-Romagna and Liguria in the North. If you’re looking for a place to start or some essential destinations to fill your itinerary, here’s a short list of must-visit locations.

Trek Through Idyllic Towns and Heritage Sites 

Tuscany is dotted with charming towns, including Montepulciano and Val d’Orcia, two beloved destinations. Each features its own distinctive history and offers stunning scenic views, quaint streets, and well-preserved medieval architecture. While we recommend visiting both, we’ve put together a snapshot of each to help you plan your tour.   

Montepulciano is a popular town in the winemaking regions of Tuscany, with landmarks including the Cattedrale di Santa Maria Assunta and the charming Piazza Grande. In fact, downtown is closed off to cars, making it easier for pedestrians to trek through these urban areas at their own pace. You may opt to climb or take the elevator up the town hall’s clock tower, where a bird’s-eye view of the city and its historical landmarks awaits.

Declared a UNESCO World Heritage site in 2004, the beauty of Val d’Orcia has been celebrated in many paintings and films as quintessentially Tuscan. Here, you can explore the idyllic town of Pienza, renowned for its well-preserved Renaissance architecture, including Pienza Cathedral and Palazzo Piccolomini. Make sure to pack your camera to capture the scenic sights as you hike through one of the most photographed locales in Tuscany. 

Agriturismo: A Fusion of Rustic Life, Warm Hospitality, and Authentic Experiences

You may have heard the term agriturismo before — but what exactly does it mean? It’s the concept of staying in an operating farm that offers resort-like amenities. In other words, it’s the perfect blend of old-world charm and contemporary travel. With many agriturismo properties offering single or extended overnight stays, visitors can experience on-site dining — complete with local olive oil, cured meats, cheese, and seasonal dishes — tour the grounds, and enjoy different activities. Agriturismo offers a way to live like a local, an opportunity to embrace tradition and experience all the area has to offer.

Things to Do in Tuscany

There are plenty of ways to keep busy in Tuscany, from touring local sights and soaking up natural hot springs to enriching your tastebuds and culinary knowledge. Discover a wealth of activities just beyond your accommodations.

Explore The Region at Your Own Pace

Care for a hike? Tuscany boasts thousands of trails and walks leading you through its picturesque countryside, connecting you to charming small towns and cities throughout the region. Whether you’re a novice or an experienced hiker, there are hundreds of trails and tours to choose from, catering to all skill levels. Many of these hikes are themed, highlighting Tuscany’s rich offerings, such as wineries, olive oil production, architectural wonders, art, and more.

If you prefer exploring on two wheels, consider embarking on a bicycle tour, a popular choice in Tuscany. These tours will take you across the rolling hills, immersing yourself in the breathtaking landscape that links charming villages in the area. Various tour options are available, ranging from single-day trips to multi-day adventures.

Find Total Rejuvenation in Tuscan Thermal Baths

Tuscany is famous for its thermal baths, or “terme,” many dating back to the Roman Empire, where the Etruscans and Romans valued the therapeutic benefits of the natural hot springs. The opulent Calidario Terme Etrusche and Terme di Saturnia are two famous thermal baths featuring cascading waters and natural pools carved into centuries-old stone. While some are luxury experiences and others rustic, visitors can choose from indoor or outdoor pools, spa treatments, mud baths, hydrotherapy, and other wellness activities at various Tuscan thermal baths.

World-Class Vino and Michelin-Starred Restaurants — Saluti!

Food and wine are central to the Tuscan experience, rooted in its historical identity as an agricultural region. The fall harvest season, in particular, is an ideal time to experience its culinary delights. Visitors have the opportunity to explore picturesque vineyards and indulge in wine tastings. If you’re a wine enthusiast, chances are you’ve already savored the rich flavors of Chianti Classico and Brunello di Montalcino, two of Tuscany’s most recognized appellations. Wine isn’t just a beverage here; it’s a way of life. As of 2023, there are nearly 100 operational wineries in Tuscany, each contributing to the region’s rich viticultural heritage.

Tuscany is home to 11% of Italy’s Michelin-starred restaurants, with 41 as of 2023. Located in Florence, Enoteca Pinchiorri is the most decorated restaurant in Tuscany, having been awarded three prestigious Michelin Stars. Visitors celebrate its dishes for striking a balance between opulence and simplicity, treating guests to an unforgettable culinary journey. If you’re looking for alternate fine-dining options, Forte de Marmi, Viareggio, and Florence have the most Michelin-starred restaurants in Tuscany. Simply put, there is no shortage of exquisite dining, with each option offering inspired creations.

Craft Your Own Regional Delights

Feeling inspired by the Tuscan countryside and want to learn to cook like a local? There are plenty of options for cooking classes that teach you how to prepare many local dishes. Simple day classes led by local instructors demonstrate traditional cooking techniques using local produce. Intensive cooking classes are also available, featuring multiple days or weeks working under instructors, often in a professional kitchen. Whether simple or intensive, these sessions often include basic wine pairing knowledge and let students enjoy the meal prepared at the end of the class.

Ready to Start Planning? 

By now, it’s easy to see that there is a wealth of things to do while staying in Tuscany at Casali di Casole. While summer may be the favored season for many, a visit during the autumn months offers a fresh perspective. We are here to help you craft an unforgettable off-season Tuscan experience. Embrace the allure of Tuscany in the fall and let its beauty leave an indelible mark on your memory.