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 ancient 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 village to village along the spectacular coast. Our overnights are in settings as charming as our hikes, including a 15th century palazzo in the walled village of San Quirico d’Orcia, a castle-turned-hotel in tiny medieval Sorano, and a country estate among lush vineyards in the high Maremma.

Itinerary at a Glance

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

After meeting in Florence, we head out for a walking tour of glorious medieval Siena, whose shell-shaped town square, the famous Campo, has been the focus of Sienese life since 1340. Countryside walks bring us to cinnamon-brick Monte Oliveto Maggiore, Tuscany’s grandest monastery, and to the Abbey of Sant’Antimo, perhaps the largest and finest example of Romanesque architecture in Tuscany. We also sample wines in Montalcino, known for its ruby-red Brunello de Montalcino. Our beautiful hotel is in a 15th century palace in San Quirico d’Orcia.

Days 3-4
Pienza / Pitigliano / Sorano

Before setting off on our morning hike, we explore Pienza, known as “the Pearl of the Renaissance.” Designed by architect Bernardo Rossellino, Pienza is a prime exemplar of 15th century Italy. From the wine-producing town of Pitigliano, a medieval masterpiece set in one of Tuscany’s wildest regions, we follow Etruscan pathways to Pitigliano’s undiscovered sister village, Sovana, with its ancient Etruscan tombs with rock-cut facades. Our base is the hilltown of Sorano and our hotel is in the 11th century Orsini fortress.

Days 5-6
Coastal Tuscany / Massa Marittima

On Tuscany’s sun-splashed coast, where lush vineyards overlook the sea, we catch a ferry 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 rolling vineyards surrounding 13th century Massa Marittima, an unknown gem in the heart of southern Tuscan wine country. Our hotel is just outside the town’s historic center, with its ancient Duomo and cobbled squares.

Days 7-9
The Maremma

In the glorious Maremma, with its hidden coves and vineyards that produce “super-Tuscan” wines, we hike a spectacular seaside trail to the old Etruscan port of Populonia (with great views of the isle of Elba), walk from medieval Sassetta to Castagneto Carducci, a hilltown dating back 1,000 years, taste wines in Bolgheri, and enjoy a hands-on cooking class. Our hotel is an 18th century estate near Sassetta. Depart on Day 9 from Pisa.

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Cinque Terre Extension
Days 9-12

Hike the dramatic seaside villages of Cinque Terre on our self-guided extension.

What the Trip is Like

This trip is rated Level 3, Moderate. The hikes vary from three to 10 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