Medieval Hilltowns of Tuscany

Tuscany beckons the traveler with exquisite landscapes unchanged in centuries, towns still held within their medieval walls, and a cuisine and wines renowned throughout the world. Our insider’s journey brings you the best of Tuscany, walking in Siena’s Renaissance-era piazza and the hidden gem of hilltop Sovana, with its Etruscan tombs, hiking along the coast and in the mountains of dreamy Elba, the island of Napoleon’s first exile, and climbing the towers of San Gimignano, the most revered of Tuscany’s enchanting medieval hilltowns. With memorable trailside picnics of Tuscan specialties, visits with wine and cheese-makers and sampling their delicious wares, and a cooking class in the art of Tuscan cuisine, this is the ultimate cultural and hiking journey through Italy’s most treasured realm.

Itinerary at a Glance

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Days 1-2
Florence / Siena / San Quirico d’Orcia

From Florence, we head out for a walking tour of glorious Siena, with its shell-shaped piazza, the famous Campo. Country walks bring us to cinnamon brick Monte Oliveto Maggiore, Tuscany’s grandest monastery, and through forests and vineyards with marvelous views. We also sample the wares in Montalcino, Tuscany’s most important wine town.

Days 3-4
Pienza / Pitigliano / Sovana

We explore medieval Pienza, a perfect window into 15th century Italy, and from the ancient town of Pitigliano, hike to the undiscovered hilltown of Sovana, with its marvelous Etruscan tombs.

Days 5-6
Elba

A ferry brings us to Elba for breathtaking hikes on this magical island surrounded by the wide, blue Tyrrhenian Sea. After a hike on the “Via Crucis,” a path leading to the shrine of Madonna del Monte, we enjoy a wonderful cooking class.

Days 7-9
Volterra / San Gimignano

Back on the mainland, we head to Volterra, the ancient Etruscan city of Velathri. In this walled medieval town we visit the Etruscan Museum, see how pecorino is made at an artisanal farm (and sample it, of course), and explore the abandoned medieval village of Castelvecchio. In charming San Gimignano, we climb the tower in the town hall for views over the countryside, and hike to a castle for a picnic with fantastic views of San Gimignano’s towers soaring on the horizon. Depart on Day 9 from Florence.

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What the Trip is Like

This trip is rated Level 3, Moderate. The hikes vary from 2 to 6 miles on moderate to steep trails. Although you carry only a daypack on the hikes, there are a few steep ascents and descents, and some of the trails are on rocky terrain, so we recommend you make a special effort to be in good physical condition. Daily brisk walking and/or regular hiking (or using a stair-climbing machine at your gym) are excellent preparatory exercises. You should wear well-broken-in hiking boots for maximum comfort on the trail. Our van usually meets us at midday, bringing a wonderful picnic lunch of local breads, cheeses, fruits, and wines. On "town" days we will have lunch at local cafes. Our luggage is transported for us by van, so it is always possible to ride in the van if you wish to opt out of a day's hiking. Please note that in Europe, the dinner hour is considerably later than what it is in the US. We do our best to secure early reservations for our groups, but most often the evening meal will be at 7:30 PM.

Explanation of Trip Levels