From Medieval Hill Towns to Seaside Villages


From Tuscany to the sea, our journey explores two irresistible realms of Italy in superb WT style, with hikes to hilltop villages, bountiful picnics, and Trip Leaders who bring this celebrated land to life. Tracing an arc from Cortona to Siena, Pienza, Volterra, and San Gimignano, with its famous crown of towers, we set out for hikes through ancient vineyards and to tiny hamlets. We’ll also hike to an organic farm, meet vintners and cheesemakers, and enjoy the pleasures of Tuscany’s cuisine and wines. We end with a flourish, visiting graceful Lucca, with its intact Renaissance walls, and hiking the seaside trails of Cinque Terre to five cliff-perched villages wedged into the mountainous Ligurian Coast.

Itinerary at a Glance

Day 1

In Fiesole, an ancient town spread over a cluster of hills just above Florence, we walk to Monte Ceceri, a hill near Fiesole where Leonardo da Vinci conducted experiments with his flying machine—in 1506!

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Days 2-4
Chianti / Casali in Val di Chio / Cortona

We visit the tiny wine town of Greve, surrounded by Chianti’s vineyards, then head to the green hills, stone villages, and olive groves of the Tuscan countryside, where our hikes bring us to remote hermitages and family-owned vineyards. We hike to the stunning hill town of Cortona, savor the exquisite setting of tiny Pienza, a gorgeous gem surrounded by rolling hills of wheat and olive groves, and hike to a family farm for lunch. Our overnights are in a Tuscan dreamscape: the stone-built villas of a private, family-owned 15th century estate. We’ll hike the estate’s trails and enjoy a private tasting in the historic wine cellar.

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Days 5-6
Siena / San Gimignano / Volterra

A morning hike brings us to the ravishing medieval city of Siena for lunch, and we explore Volterra, with its Roman theater and heritage of Etruscan culture. From hilltop San Gimignano, we hike down through olive groves to a small village for a picnic with views back toward San Gimignano’s soaring towers.

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Days 7-11
Lucca / Cinque Terre Villages

After a walk on Lucca’s city walls and a dinner of local fare, we head to Cinque Terre, where centuries-old villages with tiny harbors are carved into the Ligurian Coast. We’ll hike through this spectacular landscape, where seaside trails contour through vineyards to connect these unique villages. Local ferries and coastal trains to and from our trailheads give us fantastic access to Cinque Terre. Depart on Day 11 via Pisa.

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Enjoy a warm welcome on a historic private estate near Cortona—our lodging for three nights
Explore the gorgeous hill towns of Cortona, Pienza, and San Gimignano
Spend three days in Cinque Terre, with hikes to spectacular Vernazza and other villages
Delightful wine tasting, sumptuous picnics, and perfect hikes through exquisite landscapes
Trip Leaders who know all the best trails, cafes, and local delicacies!


Length: 11 days
Cost From: $6195  
Arrive: Fiesole, Italy
Depart: Pisa, Italy
Lodging: 10 nights hotels, including 3 nights in villas on a private 15th century estate and 3 nights in Cinque Terre
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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