From Medieval Hilltowns to the Ligurian Sea


In Tuscany, ochre-colored hilltowns rise above a painterly landscape of cypress and olive groves. Our cultural hiking adventure pairs the beauty of this enchanting region with the Cinque Terre, five lovely villages tucked beside the sparkling sea. To savor these dreamy landscapes, we’ll explore the medieval Tuscan gems of Sovana and Siena, and enjoy a sunset hike into legendary San Gimignano. In the Cinque Terre, home of fabulous seafood and sweet Sciacchetra wine, our hikes bring you to tiny villages of pastel-hued palazzi. Gourmet picnics, wine tastings, and a cooking class round out our captivating experience of Italy’s la dolce vita.

Itinerary at a Glance

Days 1-5
Rome / Tuscan Villages

From Rome, we head to medieval Pitigliano, then hike along ancient Etruscan pathways to Sovana, with its impressive Etruscan tombs. After exploring tiny Pienza, a perfect window into 15th century Italy, we hike to San Quirico d’Orcia, an exquisite walled town of Etruscan origin, and on to Montalcino, known for its ruby-red Brunello di Montalcino (with a wine tasting, of course!). We explore Siena’s scallop-shaped campo, then hike through vineyards right into San Gimignano, just as the late afternoon sun burnishes its medieval stone towers in golden light.

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Days 6-10
Trails of the Cinque Terre / Italian Riviera

The five hamlets of Cinque Terre are wedged into a rocky coast terraced with ancient vineyards. Our trails lead to the fishing village of Riomaggiore, and from the sandy beaches of Monterossa to Vernazza’s tiny picturesque harbor and cliff-perched Corniglia. We also explore the Riviera resort town of Sestri Levante, where we have a lesson in making the area’s famous—and absolutely delicious—pesto, visit below-the-radar Camogli, and enjoy famed Portofino, where we hike to an isolated village reached only on foot or by boat. Depart on Day 10.

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Hike to charming medieval hilltowns, explore Etruscan ruins
Stroll through Siena, with its exquisite scallop-shaped piazza
Discover San Gimignano, the quintessential walled Tuscan town
Visit local wineries, taste fine wines including Vernaccia and Brunello di Montalcino
Hike seaside trails to the most beautiful villages of the Cinque Terre, explore Portofino
Delight in charming hotels, from a restored palazzo to a welcoming seaside hotel
Savor picnics of local culinary treats, including zesty salumi, aged cheeses, and foccacia al stracchino


Length: 10 days
Cost From: $5695  
Arrive: Rome, Italy
Depart: Pisa, Italy
Lodging: 9 nights fine hotels, including a restored palazzo
Meals: All meals included except 3 dinners
Activity: Cultural Adventures, Hiking / Trekking
Trip Level:

A mix of easy to moderate walks and hikes, 3-6 hours a day, van support (for luggage or if you wish to skip a day’s hike)

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