Tuscany beautifully combines breathtaking scenery, history, and some of Italy’s best made wines. In this enchanting landscape of rolling hills and winding roads, you’ll find glorious sunflower fields, ancient olive groves, medieval ruins, walled cities, wild forests, and of course, world-class vineyards.

Siena

Siena epitomizes a classic medieval city with its Gothic appearance acquired between the 12th-15th centuries which has all been well-preserved. Head to Torre del Mangia for views across Piazza del Campo and if you’re feeling adventurous climb up 400 steps to the top of the tower for a 360 degree view of the surrounding countryside.

Badia a Coltibuono

Located in the heart of the Chianti region, Badia a Coltibuono has for 1,000 years been an important farm and its land has been producing excellent wines and oils for centuries. The historic winery was originally a monastery dating to the 11th century which was then converted into a vineyard owned by a local family.

Castellina in Chianti

Castellina in Chianti is a small town in the heart of the Chianti region with a lovely medieval closed walkway. The city’s origins go back to Etruscan times which you can experience with the local archaeological museum.

San Gusme

The picturesque town of San Gusme is a true gem and stands untouched by time. The quaint hilltop village sits perched atop a hill that provides beautiful panoramic views of the surrounding Tuscan countryside and gives off a down to earth Italian charm vibe.

Castello Brolio

Castello Brolio is a picturesque castle and winery set in the stunning Chianti region of Tuscany. With its gentle hills, valleys, and thick woodlands of oaks and chestnuts, the 1,200 hectares of property include almost 240 hectares of vineyards and 26 of olive groves.

Montepulciano

Located in the southern part of Tuscany, Montepulciano is a medieval town full of Renaissance architecture where the influence of the great Medici family can still be felt. The architecture is so authentic that no major building works have been carried out here since the late 1500s.

Siena has always been a personal favorite as a base to explore Tuscany. Siena is nearly smack in the middle of the region, has a town with all the amenities you will need, and is a beautiful city to discover in its own right.

Another option for a more intimate experience is to find a villa or winery to stay for a few days. There are thousands of small villas and wineries that double as a B&B, which would allow you to really immerse yourself in the Tuscan countryside.

Dining in Tuscany…

Both lunch (“pranzo”) and dinner (“cena”) usually consist of several courses; the pasta course (“primo”) takes the place of a soup course, not a main dish, followed by the meat dish (secondo) then a desert if you have it in you.

La Taverna di San Giuseppe

This typically Tuscan location dates back to 1100 – and is situated in the heart of the historic center of Siena, 400 meters from the famous Piazza del Campo. In the evening the tables are lit by candle light creating a magical dining atmosphere.