Country Walks from Southern Tuscany to the Sea

Medieval Hilltowns & Coastal Trails

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"I just loved it. Every day we said ‘can it get any better than this?’ and every day it did." Alice Sherman, Shaker Heights OH

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 Tyrhennian 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 locations as charming as our hikes, including a 15th century palazzo in the completely walled village of San Quirico d’Orcia, an imposing castle-turned-hotel in the tiny medieval hilltown of Sorano, and a country estate high in the Maremma.

Below is an Itinerary-in-Brief. To view a complete Detailed Itinerary, Download Full Itinerary or Email our Area Specialist

Itinerary-in-Brief

Days 1-2
Siena / San Quirico d’Orcia

We meet in Florence and head to 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, perhaps the largest example of Romanesque architecture in Tuscany, for a picnic of Tuscan specialties and wine tasting. An afternoon visit brings us to Montalcino, famed for its ruby-red brunello de montalcino wines. Overnights are in the walled village of San Quirico, with its Estruscan origins.

Days 3-4
Pienza / Pitigliano / Sovana / Sorano

From San Quirico d’Orcia, we hike a remote trail to glorious Pienza, as complete a Renaissance vision as any in Italy, and then from San Rocco right to our fortress-hotel in Sorano on an Etruscan path hand-cut into the tufa rock. Another fine hike brings us across vineyards from the hilltop town of Pitigliano to Pitigliano’s undiscovered sister village, Sovana. Overnights are in a majestic converted fortress that stands above the lovely Estruscan town of Sorano.

Days 5-6
Costa degli Etrusci / Massa Marittima

On the Coast of the Etruscans, we hike to Cala di Violina, a beautiful beach along crystal-clear seas near picturesque Castioglione della Pescaia, with a beach picnic, and we hike the wooded hills and vineyards around Massa Marittima. Our hotel is in 13th century Massa Marittima, a gem of a hilltown in southern Tuscan wine country.

Days 7-9
Country Estate / Maremma

We hike along the sea to Populonia, once an Etruscan port and today a charming medieval town. The next day we hike to the medieval village of Sassetta for lunch, with an afternoon visit to the walled town of Bolgheri to celebrate with a special tour and wine tasting. Overnights are at an 18th century country estate in the high Maremma. Depart on Day 9 from Pisa or join our Cinque Terre Extension.

Cinque Terre Extension (Available for all Italy trips)

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.

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Tour Costs $3795 (13-15 members) $3995 (10-12 members) $4195 (6-9 members) Single supplement: $495 Cinque Terre extension from: $475 *Prices are for 2008 dates only **Airfare is not included in Tour Cost unless indicated

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