Monteriggioni, Tuscany

Built in the 14th and 15th centuries, medieval hilltowns tower above the Tuscan landscape. Our hikes bring us from one hilltown to another as we savor the heritage and cuisine of Tuscany.

Photo by Brian McGilloway

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Medieval Hilltowns of Tuscany

Siena, Massa Marittima, Bolgheri, and the Maremma

On delightful country walks—the ultimate way to see Italy’s beauty—we experience 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 rocky coast at the Maremma, where Tuscany meets the wide, blue Tyrrhenian Sea. With idyllic days of walking and memorable trailside picnics of southern 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.

Highlights

  • Hike to jewel-like hilltowns in the wine country and on the Mediterranean Coast
  • Charming hotels from a restored palazzo to a converted medieval fortress
  • Wine tastings, picnics of southern Tuscan culinary treats, cooking lesson

Details

  • 9-day trip begins in Florence and ends in Pisa
  • 2 nights in small hotels, 2 nights in converted castle, 2 nights in restored palazzo, 2 nights in country estate
  • All meals included except 3 dinners
  • Easy to moderate trails, 3-6 hours a day, van support

Tour Costs

$4395 (12-15 members)
$4695 (9-11 members)
$4895 (6-8 members)

Single supplement: $795

Prices are for 2010 dates

Departures & Leaders

Apr 16-24, 2010  Lisa Halderman
   Tania Masi
May 7-15, 2010  Ellen Santucci-Masi
   Giuseppe Aruta
Sep 3-11, 2010  Lisa Halderman
   Giuseppe Aruta
Sep 18-26, 2010  Lisa Halderman
Oct 1-9, 2010  Lisa Halderman
   Sergio Mastroberardino

Suggested Reading

Reading list, click here.

Itinerary at a Glance
Medieval Hilltowns of Tuscany route-map

Days 1-4
Florence / Siena / San Quirico d’Orcia / Sorano

From 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. Country walks bring us to cinnamon-brick Monte Oliveto Maggiore, Tuscany’s grandest monastery, and we sample wines in Montalcino, known for its ruby-red Brunello de Montalcino. We also hike Etruscan pathways to the hilltown of Pitigliano, a medieval masterpiece set in one of Tuscany’s wildest regions, and to Pitigliano’s undiscovered sister village, Sovana. Our beautiful hotels are in a 15th century palace in San Quirico d’Orcia and in Sorano’s 11th century Orsini fortress.

Days 5-6
Coastal Tuscany / Massa Marittima

On Tuscany’s sun-splashed coast, where lush vineyards overlook the cobalt sea, we 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 in the village 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, walk from Castagneto Carducci to medieval Sassetta, 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.

This is the Itinerary-at-a-Glance. For the complete trip description, Download Full Trip Brochure

Cinque Terre Extension
Days 9-12

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

Please call us or Download Full Trip Brochure for more information