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.
This was a great itinerary that was well organized and well executed. We had great food and wine at every destination and very well-informed trip leaders.
— Bill B., Highland Park, IL
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.
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.