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