From Medieval Hilltowns to the Ligurian Sea


The ochre-hued hilltowns of Tuscany, Cinque Terre’s spectacular coastal hamlets, and the cypress-clad harbors of the Italian Riviera are the perfect settings for our stunning hiking and cultural adventure. Experience these enchanting regions the WT way, with unique hikes, bountiful picnics, wine tasting, and savoring the joys of Italian life and culture. Between Tuscany and the sparkling sea, we visit private wine cellars, hike to an organic farm, climb balcony trails, learn the secrets of pesto-making, and have a private alfresco dinner at our own exclusive villa. Our Trip Leaders bring this land to life for us every day, sharing their passion for la dolce vita.

Itinerary at a Glance

Day 1
Fiesole / Florence

From Fiesole, overlooking Florence, we hike to the gorgeous town of Settignano, once home to the artist Michelangelo, with views stretching down to Brunelleschi’s grand Duomo.

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Days 2-3
Chianti / Casali Val di Chio / Cortona

The green hills, stone villages, and famous vineyards of Chianti surround us on our hike (with a stop for wine tasting!), and we explore the classic hill town of Cortona of Under the Tuscan Sun fame. Our overnights are in a Tuscan dream: stone-built villas that are part of a 15th century private estate. We’ll be welcomed to the olive orchards and the estate’s wine cellar for a taste of its robust red wine.

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Days 4-5
Pienza / San Gimignano / Volterra

We savor the beauty of medieval Pienza, hike to a family farm for lunch, and visit Etruscan Volterra. One hike brings us through olive groves and fields of sunflowers right through the gates of San Gimignano as the late afternoon sun casts its glow on the medieval towers.

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Days 6-7
Cinque Terre / Vernazza / Corniglia

Our trails lead through Cinque Terre’s vineyards to a chapel overlooking the sea, and along the rocky coast from impossibly picturesque Vernazza, with its brightly painted homes and cobbled piazze, to tiny Corniglia, on a promontory 300 feet above the Mediterranean.

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Days 8-10
Italian Riviera / Portofino

From elegant Portofino, with its pastel-colored tower-houses, a balcony trail brings us to the picturesque village of San Fruttuoso for a seaside lunch—perhaps steamed mussels or fresh grilled calamari—and a chance for a post-hike dip. Depart on Day 10.

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Fiesole, an ancient town overlooking magnificent Florence
Medieval hilltowns of Pienza and San Gimignano
Cliff-perched coastal villages of Cinque Terre
The Italian Riviera’s charming towns, including elegant Portofino
Delightful accommodations, including a private estate owned by an Italian noble family


Length: 10 days
Cost From: $5595  
Arrive: Fiesole, Italy
Depart: Pisa, Italy
Lodging: 9 nights fine hotels, including a restored palazzo
Meals: All meals included except 2 dinners (B=Breakfast, L=Lunch, D=Dinner)
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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