Tuscany and the Cinque Terre

From Medieval Hill Towns to Seaside Villages


We bring you to two irresistible Italian realms in full WT style, with stunning hikes each day and expert Trip Leaders who bring this celebrated land to life. Our hikes cross Tuscany’s harmonious landscape, discovering terraced vineyards, tiny hamlets, and classic hill towns on our way from the walled village of San Quirico d’Orcia to Volterra, with its Etruscan origins. After a walk on Lucca’s historic walls, we head to Cinque Terre, where five ancient villages nestle on cliffs and along deep coves on the Ligurian coast. We connect these seaside villages with breathtaking hikes, sample Ligurian cuisine (think fresh seafood!), and ferry to Palmaria Island for a final hike with spectacular Cinque Terre panoramas.

Itinerary at a Glance

Days 1-2
Greve / San Quirico d’Orcia / Pienza / Montalcino

Heading into Chianti’s vineyards, we’ll stretch our legs on a hike and enjoy a picnic at a family-run winery, then explore the charming walled town of San Quirico d’Orcia. From tiny Pienza, a prime exemplar of 15th century Italy, we hike the iconic landscape of the Val d’Orcia, with its patchwork of rolling wheat fields, cypress-lined roads, and stone farmhouses. We’ll taste wines at medieval Montalcino, known for its deep red Brunellos.

Relais Palazzo del Capitano
San Quirico d’Orcia, Italy
Days 1 to 2 (2 nights)
Days 3-4
Siena / San Gimignano / Volterra

Siena is a ravishing medieval city and we’ll stroll its back lanes and scallop-shaped piazza, surrounded by a majestic ensemble of Gothic architecture. In San Gimignano, with its crown of stone watchtowers built by feuding nobles, we hike down through olive groves to the village of San Donato for a picnic lunch. At atmospheric Volterra, we visit the Roman theater and Etruscan ruins.

Hotel La Collegiata
San Gimignano, Italy
Days 3 to 4 (2 nights)
Days 5-6

We walk the remarkable Renaissance-era city walls in Lucca, birthplace of Puccini, attend an evening concert, and hike on an ancient aqueduct that crosses the serene Vorno Valley.

Hotel Ilaria
Lucca, Italy
Days 5 to 6 (2 nights)
Grand Universe Lucca
Lucca, Italy
Days 5 to 6 (2 nights)
Days 7-10
Cinque Terre Villages

The five Cinque Terre villages are centuries-old towns on the cliffs of the Ligurian coast. Our hikes connect the impossibly picturesque settings of Vernazza, Corniglia, and Manarola. Ferrying out to Palmaria Island, part of the Cinque Terre World Heritage area, our final hike brings us spectacular views along the entire Ligurian coast. Depart on Day 10 via Pisa.

Hotel Porto Roca
Monterosso, Italy
Days 7 to 9 (3 nights)



Visit the vineyards of Chianti, with a picnic at a family-run winery
Explore and hike from the Tuscan towns of San Quirico d’Orcia, Pienza, Siena, and San Gimignano
Walk the famed coastal trails that connect the five Cinque Terre villages
Ferry to Palmaria Island for a spectacular hike and coastal views
Trip Leaders who know all the best trails, trattorias, and local delicacies!


Length: 10 days
Cost From: $6195  
Arrive: Florence, Italy
Depart: Pisa, Italy
Lodging: 9 nights hotels
Meals: All meals included except 4 dinners as indicated in the Detailed Itinerary (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

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