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Top 30 Destinations by Personality Type
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Tuscany/hill towns, Italy

Great Destination:

Value for Money:

Total Stars:

Personality Types that Like it Best

Did You Know … ?

  • Today there are 14 tower houses in San Gimignano, but once there were 72.
  • Frances Mayes’ “Under the Tuscan Sun” is set in and around Cortona.
  • A Volterra artist was called “the underwear guy” after he painted over the nudity in Michelangelo’s “The Last Judgment.”
  • Experts estimate that Tuscany harbors more than 2 trillion cubic feet of untapped Carrara marble.
  • Volterra was first in Italy to build a town hall; the building is still on the central piazza.

Medieval walls, Chianti wine

Tuscany, which stretches across north central Italy, appeals to tourists in many ways: beautiful cities, rolling hills and lush valleys, local wines (think Brunello, Chianti, Montepulciano) and cheeses, good restaurants, natural hot springs — plus the iconic cypress trees and an incredible store of invaluable artworks.

It’s a dream package and enough to make Tuscany wildly popular, but wrap all that up with walled hill towns that often have roots predating the Romans and the destination rates tops with all personality types. There is something for everyone, whether it is dallying over pasta and wine, chilling out at a spa or biking and hiking through the fabled Tuscan hills.

As for hill towns, the following are prominent among those that lure visitors and generate top ratings:

  • Cortona. Etruscan tombs dot the hill where Cortona sits, but the main appeal today is the medieval town center within medieval walls and the views across the countryside. It has its share of artistic riches, too.
  • Fiesole. This small town also claims Etruscan roots, but the visible antiquities are Roman: a theater, a necropolis and thermal baths. It also claims medieval architectural treasures, in combination with scenic views.
  • Montalcino. From its hill, this center of art overlooks sweeping vineyards, which provide grapes for Brunello red wine. Key structures in the walled town date from the 13th and 14th centuries.
  • Montepulciano. This village gave its name to one of Italy’s better-known wines. Surrounded by 15th century walls, the town is chockablock with medieval and Renaissance churches and palaces. A spa is nearby.
  • Pienza. The center of this village was rebuilt in the 15th century as the ideal Renaissance town, and so it has remained.
  • San Gimignano. Here is the picturesque town with the famous tower houses. There is more — an Etruscan history, a walled medieval town center — but the towers alone fill its piazzas with visitors.
  • Volterra. This walled town was the last Etruscan site to fall under the Romans, and the evidence shows in museums and even a city gate. Volterra has a Roman theater and forum. Its town hall was the model for city halls in Tuscany.

Things to do for Venturers

  • See cooking demonstrations, or take hands-on lessons in Tuscan ways with food.
  • Tuscany has quite a few government-supported agritourism sites, essentially farms where owners build a tourism business by renting out a few rooms and, under terms of the support, must serve meals made from foods they grow. Choose a farm stay and enjoy the meals.
  • Walk outside of Cortona to find unique attractions. A 45-minute walk takes you to Le Celle di Cortona, a Franciscan convent which has the cell where St. Francis stayed when he preached there in 1211. Also, walk up hill to the 16th century Medici fortress above the town.
  • Plan a multiday self-guided tour cycling from hill town to hill town.
  • Fiesole provides views over Florence, but time your visit to also attend a summertime theatrical or musical event in the town’s Roman theater. The performances are part of a package called Fiesolan Summer.
  • Leave mainland Tuscany. Take a seven-day sea kayaking and camping trip on the island of Elba, which is part of the Tuscan Archipelago National Park. Take courses in sea kayaking if needed.

Things to do for Centrics

  • For history buffs, there are several hill towns where you can look at the interior of Etruscan tombs. Also, at Volterra’s Guarnacci Etruscan Museum, see the very extensive collection of Etruscan urns.
  • Go to Pienza to see what folks in the Renaissance era thought a model town center should look like.
  • Wander Cortona’s medieval streets, and stroll along the equally old walls for great views of the countryside.
  • Volterra is the place to buy alabaster. Visit one of the workshops there to see how the artisans work, then buy your souvenirs.
  • If the timing works, follow your taste buds to Pienza for the annual Festival of Cheese on the first Sunday in September. The town is considered the capital for pecorino cheese.
  • Climb to the top of the Town Hall tower in Montepulciano for views of the town and beyond, to the village of Radicofani, the Orcia Valley and Lake Trasimeno. Also, taste the Montepulciano wine here in one of the town’s many wine shops.

Things to do for Authentics

  • Plan a romantic week in a countryside villa. Your honeymoon, maybe?
  • Get to San Gimignano before the crowds, if you can, for the best photos of the tower houses. Then, drop in at the local torture museum! (See the movie, “Tea With Mussolini,” before you make this trip.)
  • Have lunch in an outdoor cafe on the piazza of any of the hill towns. Drink the local wines (Brunello, Chianti, Montepulciano) with this (or any) meal. Sample the locally made olive oils and cheeses, too.
  • Given the huge amount of fine art found in Tuscany, look in the churches, palaces and museums for the best examples in every town on your itinerary. Sign on for guided tours when you risk massive art-information overload.
  • Have a massage, or a more extensive spa experience, at one of the area’s spas, such as Saturnia, Montecatini and Chianciano.
  • Play golf at Castelfalfi, near San Gimignano.

Additional Resources

For more information, consult the Official Tourism Site of Tuscany at and choose your language if necessary.