Tuscany and the Cinque Terre

From Medieval Hill Towns to Seaside Villages

Overview

Discover two irresistible Italian realms in WT style, with stunning hikes each day and expert Trip Leaders who bring this celebrated land to life. We hike across 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, and 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 5-9
Lucca / Cinque Terre Villages

In Lucca, we walk the Renaissance-era walls, then head to Cinque Terre to hike between centuries-old towns on the cliffs of the Ligurian coast. Our hikes connect the impossibly picturesque villages 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 9 via Pisa.

Hotel Ilaria
Lucca, Italy
Day 5 (1 night)
Hotel Porto Roca
Monterosso, Italy
Days 6 to 8 (3 nights)

Highlights

Highlights

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
Hike 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!

Details

Length: 9 days
Cost From: $5395  
Arrive: Florence, Italy
Depart: Pisa, Italy
Lodging: 8 nights hotels
Meals: All meals included except 2 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

Other Trips You Might be Interested in: