Tuscany and the Cinque Terre

From Medieval Hill Towns to Seaside Villages


Explore two irresistible Italian realms in WT style, with stunning hikes 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 San Quirico d’Orcia to Volterra. 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, 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 / Montalcino

Meeting in Florence, we head into Chianti’s vineyards for a morning hike above the medieval hill town of Greve, the hub of Chianti’s wine country. We’ll picnic at a family-run winery then head to the walled town of San Quirico d’Orcia, where our hotel is a beautifully restored 14th century mansion. After exploring the town of San Quirico, we hike the iconic landscape of the Val d’Orcia, with its patchwork of rolling wheat fields, narrow, cypress-lined roads, and stone farmhouses. We enjoy a tasting of the famed Brunello di Montalcino wine, otherwise known as “nectar of the Tuscany gods,” and spend the afternoon in the small village of Montalcino.

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

We take a morning hike right from our hotel through rolling hills of wheat, olive groves, and classic stands of cypress trees. After a picnic lunch at the Pieve di Corsignano next to an ancient chapel, we walk through Pienza, a gorgeous medieval gem with splendid buildings from the 1400s. In the afternoon, we explore the ravishing medieval city of Siena, whose spiritual heart is the sloping, scallop-shaped piazza, Il Campo, surrounded by a majestic ensemble of Gothic architecture. We’ll walk the back lanes and hidden squares of Siena, then head to San Gimignano, known for its crown of stone watchtowers built by the feuding nobles of the 12th and 13th centuries. On Day 4, we hike from San Gimignano through holm oak forest, passing vineyards and olive groves to a ridge with excellent views. Later, we drive to Volterra, a town full of the lore of the Etruscan culture, and wander the tiny cobbled streets and explore the Roman theater and bath complex.

Hotel la Cisterna
San Gimignano, Italy
Days 3 to 4 (2 nights)
Days 5-9
Lucca / Cinque Terre Villages

Lucca is a graceful provincial capital enclosed in an imposing ring of Renaissance-era walls fronted by gardens. We walk the walls, attend a concert in a church dedicated to Puccini, who was born here, and head to Cinque Terre, where five centuries-old towns are carved into the Ligurian coast. Hiking stone-paved trails that contour steeply through terraced vineyards, we connect these unique villages, including impossibly picturesque 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 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)



Visit the vineyards of Chianti, with a picnic at a family-run winery, and enjoy a tasting of the famed Brunello di Montalcino
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!


Length: 9 days
Cost From: $5295  
Arrive: Florence, Italy
Depart: Pisa, Italy
Lodging: 8 nights hotels
Meals: All meals included except 3 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 (for luggage or if you wish to skip a day's hike)

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