4 Historic Hilltop Towns in Tuscany

by Christopher Atwood

Tuscany is not exactly a travel secret. Florence alone receives over 20 million tourists each year – in a city of less than 400,000 residents! Million others flock to popular sites – Siena, San Gimignano, and Pisa. Why? It's simple:

· rolling vineyards in the Chianti countryside

· the red sun setting behind Florence’s Ponte Vecchio

· hot air balloons floating over hilltop towns and golden fields

Tuscany's popularity has become a blessing and a curse. Hotels can book up 6 months in advance. Popular tours sell out fast. With so many Americans at Tuscany's big sights, it's easy to feel like you're visiting Epcot and not experiencing the real Italy.

Download Our 'Untouched Tuscany' Itinerary


But, don’t worry. Tuscany isn’t Disney World. The true Tuscany – a land rich in time-honed traditions – thrives just off the touristy track.

In our Tuscany, you'll sip Chianti in family-run wineries' private cellars

In our Tuscany, you'll taste pecorino at the farm where the cheese is made 

In our Tuscany, you'll gaze at medieval towns while strolling an ancient path.

Are you tempted by Tuscany? We're sharing 4 tantalizing Tuscan towns – each easily reached from Florence or Siena... but minus the big crowds:


The hilltop hamlet of Monteriggioni is tucked in the countryside near Siena. Immaculately-preserved, the town of Monteriggioni is in fact a walled castle – crowned in impressive towers. Visible from the vineyard-draped valley below, Monteriggioni was built between 1212 and 1219. Fourteen intact towers and two main gates adorn this castle-city’s stone walls. Travelers here can even arrive at Monteriggioni via a 700-year-old pilgrimage path, traversing farms and olive groves on their way.



The history of Radda in Chianti -- also in the province of Siena -- dates back to the 9th century. This tiny gem of a town is encircled in medieval walls. Easily reached from either Florence or Siena, Radda in Chianti boasts winding stone streets and panoramic views of the Tuscan wine country. Located near some of Tuscany’s main roads, Radda in Chianti makes for a scenic stop during a full-day wine tour or an idyllic base to savor the surrounding countryside and towns.



Barga is a postcard-perfect mountain town in the north of Tuscany. Perched between the snow-capped Apennines, which locals call the Tuscan Alps, Barga is surrounded by fog-laced woods and rushing rivers. Active travelers can enjoy the Tuscan landscape in each season here -- hiking, biking, kayaking and skiing. Barga also boasts one of Tuscany’s best-preserved Romanesque churches. Barga is an easy day trip from Lucca or a worthy stopover for those seeking a calm escape surrounded by natural beauty.

Lucca in Tuscany


While much of Tuscany is home to medieval towns, Pienza is an icon of Renaissance design and architecture. Located in the rustic Val d’Orcia region, Pienza is framed by green valleys, sunflower fields and lush vineyards. From here, travelers can enjoy day trips to the famous towns of Montalcino and Montepulciano. Food-loving visitors might spend the day sipping Brunello wine and the local cinta senese salami at a nearby winery.


When you partner with the Italy experts, your don’t see the same old sights. We help you access the Italy most tourists never experience – immersing you in the people and places beyond the postcard. Tempted by Tuscany? Contact your travel agent (yup, we work together!) or click below to start exploring all you can do under the Tuscan sun:


Download Our 'Untouched Tuscany' Itinerary


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