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

Country Walks from Southern Tuscany to the Sea

A Significant Discount on 2009 Departures is Available, Due to the Rebound in the Dollar. See Details Below Tour Costs.*

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 the tiny medieval hilltown of Sorano, and a country estate high in the Maremma.

Highlights

  • Hikes to jewel-like hilltowns in 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 class

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

$4295 (13-15 guests)
$4595 (10-12 guests)
$4795 (6-9 guests)

Single supplement: $825
Cinque Terre extension from: $535

Prices are for 2009 dates

Departures & Leaders

Sep 4-12, 2009  Lisa Halderman
Sep 19-27, 2009  Lisa Halderman
   Giuseppe Aruta, Giampiero Faga
Oct 2-10, 2009  Lisa Halderman
May 7-15, 2010
Jun 4-12, 2010
Sep 3-11, 2010
Sep 18-26, 2010
Oct 1-9, 2010

*Significant Savings Available on 2009 Departures!

The US Dollar has strengthened against the Euro, and Wilderness Travel would like to pass the savings along to you! Here's how it works: we will purchase the Euros for your trip when you sign up, which lets us lock in the current exchange rate, and guarantee your savings. To receive the discount, the first deposit on the trip ($500 per person) is non-refundable. If you prefer to have your deposit be fully refundable up to 90 days before departure, you can sign up at the regular published rate for the trip.

To find out the current discount available at today’s rate, please call us at 1-800-368-2794 or send us an email.

Suggested Reading

Reading list, click here.

Itinerary at a Glance
Medieval Hilltowns of Tuscany route-map

Days 1-2
Siena / San Quirico d’Orcia

Meeting in Florence, we head to glorious Siena for a walking tour of one of the most flamboyant examples of medieval architecture in existence. Siena’s shell-shaped town square, the famous Campo, has been the focus of Sienese life since 1340. Afterwards, a country walk brings us to cinnamon-brick Monte Oliveto Maggiore, Tuscany’s grandest monastery, nestled serenely in a cypress grove. The next day, we hike to the Abbey of Sant’Antimo and sample the wares in the wine town of Montalcino, famed for its ruby-red Brunello de Montalcino. Overnights are in the walled village of San Quirico, where our hotel is a restored 15th century palace.

Days 3-4
Pienza / Pitigliano / Sovana / Sorano

Our hike to the tiny hilltown of Pienza takes us along Etruscan pathways and across a plateau where we see an ancient Etruscan road carved out of the tufa rock. From the hilltown of Pitigliano, a medieval masterpiece set in one of Tuscany’s wildest regions, we hike to Pitigliano’s undiscovered sister village, Sovana, with its imposing Duomo. Our hotel in Sorano is located within the town’s historic 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 Cala di Violina, a beautiful beach near the picturesque old town of Castiglione della Pescaia, and through the forests and rolling vineyards that surround the 13th century hilltown of 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
Country Estate / Maremma

A spectacular hike along the seaside brings us to the charming town of Populonia, once an Etruscan port, with fantastic views en route of the beautiful Isle of Elba. Our final hike brings us from the old village of Castagneto Carducci to medieval Sassetta, with an afternoon in the walled town of Bolgheri for wine tasting. Overnights are at an 18th century country estate near the medieval village of Sassetta, where we enjoy a cooking class. Depart on Day 9 from Pisa or join our Cinque Terre Extension.

Cinque Terre Extension

The Italian Riviera ends with a dramatic flourish at Cinque Terre, five cliff-bound villages wedged into a mountainous coast terraced with vineyards. Join our self-guided 4-day extension for in-depth hikes to spectacular seaside villages.

Please call us or download the Full Trip Brochure for more information about our extensions