Roadtrip through Tuscany

Rolling hills, cypress trees, medieval towns, sunshine, wine, and pasta. What is not to love about Italy’s famous Tuscany region?

The destination for our annual Crimbo (Limbo) trip depends on seat availability on British Airways. This is because we normally have a BA Companion Voucher to use before the expiration date. Forget about long-haul flights. It is nearly impossible to snag medium-haul seats to “warm” locations such as the Canary Islands, Morocco, and Madeira. This year we settled for a road trip through the Tuscan countryside flying directly to Pisa, home of Galileo Galilei. 

With its beautiful vistas, rolling hills, miles of cypress trees, magical hilltop towns, and fantastic food scene, it is no surprise that Tuscany is a popular destination. In fact, more than half our plane was full of New Yorkers. As Tuscany is a large region, I spent far too much time researching and planning for our weeklong roadtrip before finally settling on our final itinerary.

Hilltop Towns and Medieval Towns

There are so many magical hilltop towns all around Tuscany. Each with its own unique history, UNESCO status, and of course beautiful vistas of the Tuscan countryside. These include the famous wine towns such as Montalcino and Montepulciano. Then, there are also UNESCO World Heritage Sites such as  Pienza, home of the Pecorino cheese and the ‘medieval Manhattan’ town of San Gimignano.  There are lesser-known hilltop towns such as Cortona, Volterra, and Monteriggioni which are worth a visit if you have time.

Then there are of course beautiful medieval towns with gorgeous architecture, museums, and boutique shops. Some of the famous Tuscan towns include Pisa with its iconic Torre di Pisa; walled-city of Lucca; historical Siena; and finally Tuscany’s largest town of Florence, known for its Renaissance art. So many beautiful places in Tuscany! Even with a week and a rental car, we had to carefully map our Tuscan itinerary.

Wine Regions in Tuscany

Tuscany has many wine regions, among them: Chianti (Chianti Classico), Montalcino (Brunello), Montepulicano (Vino Noblile), and Bolgheri (Super Tuscans). These iconic wines are primarily from the Sangiovese grape. However, there are strict rules for blending with other grape varietals and minimum aging requirements. Tuscany is truly a wine-lovers paradise with gorgeous views to match. Some wineries occupy an old Castello whilst others have a farm and olive orchard for a true agritourism experience. Tuscany reminds me of Napa and Sonoma in California, but less commercial unless you visit the larger establishments like Banfi. Like California, winter in Tuscany is dry with sunny days, but with frosty evenings. Many of the wineries close for the winter season so it is worth contacting specific wineries in advance.

Tuscan Specialty Food

Who doesn’t adore Italian food? We do! Beyond pasta and pizza, Tuscany has many regional specialities. For meat lovers, there is Bistecca di Fiorentina aka Florentine T-bone steak; Cinghaile (wild boar); fennel salami di Toscana; and if you are bold, trippa (tripe). As for cheese, the most famous cheese from Tuscany is pecorino, a hard cheese made from sheep’s milk from the town of Pienza. This famous cheese is often served with honey and cured meat for a ‘tagliere misto’ aka charcuterie platter. Pici is popular throughout Tuscany which is a fatter version of spaghetti absolutely tasty with a wild boar ragu or tomato-based sauce.  Like focaccia, Tuscan bread schiacciata is delightful as a classic porchetta sandwich.

Hot Springs / Thermal Bath

Outside of food, wine, and hill top towns, Tuscany has many natural hot springs and thermal baths. Known for its healing properties since ancient times, thermal baths are perfect for those cold wintry days. Some of the spa towns / natural hot springs include: Bagni li Lucca, Montecatini Terme, Bagni San Filippo, Rapolano Terme, and Bagno Vignoni. Some are free open air springs, whilst others are more modern with water sourced from the thermal springs. We originally planned a half-day trip to Bagno Vignoni  for a paid entry to Posta Marcucci but decided not to at the end. 

Final Tuscan Road Trip Itinerary

After many hours of research, we decided on the following itinerary for our Tuscan road trip. Upon arrival in Pisa, we drove to San Gimignano enroute to Montepulicano where we stayed at a wine farm for three nights with day trips to Pienza and Montalcino. Then it was up to Florence for two nights over New Year’s Eve. And finally, a stay at the newly opened La Monastica, a converted monastery, in Buggiano Castello with a visit to Lucca. More to follow…