Medieval Hilltowns of Tuscany

On delightful country walks—the ultimate way to experience Italy’s beauty—we explore Tuscany’s enchanting southern realm from Siena, a Gothic dream of a city, through wine country and hidden Renaissance hilltowns all the way to the serene coast at the Maremma, where Tuscany meets the wide, blue Tyrrhenian Sea. With idyllic days of discovery and memorable trailside picnics of Tuscan specialties, we hike to ancient abbeys and castles, to jewel-like walled towns set on promontories, and along the spectacular coast. Our overnights are in charming settings including a 15th century palazzo in the walled village of San Quirico d’Orcia, a restored country home in tiny medieval Sovana, and a serene estate among ancient vineyards in the high Maremma.

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 medieval Siena, with its shell-shaped town square, the famous Campo. Country walks bring us to cinnamon-brick Monte Oliveto Maggiore, Tuscany’s grandest monastery, and through forests and olive groves to the extraordinary Abbey of Sant’ Antimo. We also sample the wares in Montalcino, Tuscany’s most important wine town. Our hotel is a beautifully restored 15th century palace in San Quirico d’Orcia.

Days 3-4
Pienza / Pitigliano / Sovana

We explore medieval Pienza, a prime exemplar of 15th century Italy, and from the ancient town of Pitigliano, hike to the undiscovered hilltown of Sovana, with its marvelous Etruscan tombs. Our hotel in Sovana is a restored country house surrounded by olive groves.

Days 5-6
Coastal Tuscany / Massa Marittima

A ferry brings us to Isola del Giglio for a hike on this magical island surrounded by the emerald waters of the Tyrrhenian Sea. We also hike to the coast at Cala di Violina and through vineyards near 13th century Massa Marittima, an undiscovered gem in southern Tuscan wine country.

Days 7-9
The Maremma

In the glorious Maremma, with its hidden coves, sandy beaches, and vineyards that produce “super-Tuscan” wines, we hike a seaside trail to the old Etruscan port of Populonia, walk from medieval Sassetta to a hilltown dating back 1,000 years, taste the wares at a specially chosen winery, and enjoy a cooking class. Our hotel is an 18th century estate near Sassetta. Depart on Day 9 from Pisa.

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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