From the hill towns of Tuscany to the mountainside villages of the dramatic Ligurian Coast, experience two of Italy’s most beloved regions from the trail, hiking, walking, and biking your way to the Cinque Terre, Lucca, and San Gimignano. Plus, stay three nights in a delightful agriturismo in the heart of Chianti.

Activity Level: This is a Moderate Active Journey. Travelers should be reasonably fit and capable of walking or hiking for several hours at a time, occasionally over steep and uneven terrain. Travelers can expect 3 to 7 miles of hiking or walking on most days, with some elevation gains, as well as an e-biking excursion of up to 10 miles. Day-by-day activity descriptions can be found on the itinerary page at the end of each day.  Read more about Active Journeys activity levels here.

This Active Journey is limited to a maximum of 16 travelers per departure

 Hiking toward Manarola along the Cinque Terre
 Hiking along the Cinque Terre to the village of Manarola
 The village of Vernazza, along the Cinque Terre
 Cathedral Santa Maria del Fior, Duomo, in Florence, Italy
 The cathedral at Lucca
 The Island of Palmaria seen from Porto Venere
 The hill town of San Gimignano
 Main piazza of San Gimignano

Tuscany and Cinque Terre: An Active Journey

10 days from $4,899

From the hill towns of Tuscany to the mountainside villages of the dramatic Ligurian Coast, experience two of Italy’s most beloved regions from the trail, hiking, walking, and biking your way to the Cinque Terre, Lucca, and San Gimignano. Plus, stay three nights in a delightful agriturismo in the heart of Chianti.

Activity Level: This is a Moderate Active Journey. Travelers should be reasonably fit and capable of walking or hiking for several hours at a time, occasionally over steep and uneven terrain. Travelers can expect 3 to 7 miles of hiking or walking on most days, with some elevation gains, as well as an e-biking excursion of up to 10 miles. Day-by-day activity descriptions can be found on the itinerary page at the end of each day.  Read more about Active Journeys activity levels here.

This Active Journey is limited to a maximum of 16 travelers per departure

Overview

Immerse yourself in the stunning landscapes of Tuscany and the spectacular Cinque Terre on a journey by foot, bike, funicular, and train. Begin with an insider tour of Florence, then set out for La Spezia, on the dramatic Ligurian coast. Spend three days exploring the World Heritage site of Cinque Terre in depth, hiking to all five villages and the island of Palmaria and opting for a wine trek if you choose. Settle into an agriturismo in the heart of Chianti and enjoy two full days of vineyard walks, wine-tasting, cooking classes, and excursions to the nearby hilltop towns of Certaldo and San Gimignano.

Highlights Include:

  • Florence: Investigate the history and mysteries of Florence's legendary families on a unique walking tour that highlights the city’s little-known stories and symbols.
  • Cinque Terre: Go on and off the beaten trail during three full days of exploring this World Heritage site. Follow mountainside paths (or take the train) through each of the five villages, climb to Punto Mesca for extraordinary views of the entire Cinque Terre coast, and hike to secluded coves and beaches on Palmaria.
  • Lucca: Pedal an e-bike around the Renaissance walls of Lucca and follow an aqueduct into the lovely surrounding countryside. Then enjoy free time to discover this enchanting historic city on your own.
  • Chianti Agriturismo Stay: Experience the flavors and rhythms of life on a traditional family-owned farm in Chianti. Hike through vineyards and visit the wine cellar for a tour and tasting of house-made wines and other local produce. Whip up a delicious Tuscan lunch during a cooking class with a local chef and savor it with your fellow travelers. Enjoy down time to relax by the property’s pool or take walks in the countryside.
  • San Gimignano and Certaldo: Explore some of Tuscany’s quintessential hilltop towns. Hike through vineyards to Certaldo and ride the funicular up to the town’s medieval center for a walking tour and dinner. Walk a centuries-old pilgrim road on a guided tour of the World Heritage site of San Gimignano before a festive farewell dinner in one of the town’s popular restaurants.  

Itinerary

Days 1-2 —Depart Home / Florence, Italy

Depart the U.S. and arrive in Florence, the capital of Tuscany and the birthplace of the Renaissance. Transfer to your hotel in the city center and take time to get settled. This evening, meet up with your trip leader and fellow travelers for an orientation walk, followed by a welcome dinner at a local restaurant. (D) 

Day 3 — Florence

Join a local guide for a walking tour of the historic center, hearing a unique perspective on Florence’s art and monuments—and the families that made it one of Italy’s most important cities. Enjoy lunch on your own and a free afternoon to explore Florence as you wish. Gather with the group for dinner tonight. (B,D)

Walking: 2-3 hour city tour on city streets.

Day 4 — La Spezia and the Cinque Terre

Transfer to La Spezia, your base for discovering the World Heritage site of Cinque Terre National Park. Enjoy three days to explore the region surrounding the “Cinque Terre”— five jewel-like villages tucked into the folds of steep coastal mountains. Take the train to Riomaggiore, then continue on foot, following your guide along centuries-old footpaths and mule tracks to Monterosso, passing through Manarola, Corniglia, and Vernazza along the way. Hike through olive orchards, vineyards, villages, and terraced hills, looking out at the sparkling sea below, and stop for lunch along the way. You’ll have an unlimited train pass to use in case you need to take a break or wish to linger in one of the villages and catch up later. From the last village, return by train to La Spezia and check into your hotel. (B,L)

Walking/Hiking5-6 miles up-and-down, various terrain (pavement, dirt tracks, stone steps, rocky/mountainous) with 1300 ft of elevation gain.

Day 5 — Cinque Terre: Monterosso to Punta Mesco

This morning, take a short train ride to Levanto and hike through coastal forests and countryside. Climb to the Hermitage of Sant’Antonio del Mesco, a crumbling church atop the promontory of  Punta Mesco, and take in a panoramic view of the entire Cinque Terre coast. Continue to Monterosso and enjoy free time for lunch. Those who would like an additional hike may join an optional wine trek (additional cost), hiking to the spectacular vineyards of Cinque Terre, learning about the history of local viticulture and visiting a wine cellar for a tasting. Travel back to La Spezia by train and enjoy an evening at leisure. (B)

Hiking: 5-6 miles, mountainous coastal terrain with 1000 ft of elevation gain.

Optional 3-hour wine trek available in the afternoon.

Day 6 — Palmaria Island / Portovenere

A short ride on the public ferry brings you to Palmaria Island, just off the Cinque Terre coast and part of the area’s World Heritage site. Here, set out on a circular hiking route that brings you to hidden caves, stunning coves, and ruined fortresses. Learn about the island’s interesting natural history and cool off with a swim at one of the beaches you pass if you choose. Take the ferry to Portovenere, located on the Gulf of Poets, for a free afternoon to relax in a café or meander the town’s medieval streets. Return to La Spezia by ferry and enjoy dinner at a local restaurant. (B,D)

Hiking: 3 miles, gentle trails with 600 ft of elevation gain.  

Day 7 — Lucca / Chianti

Travel back into Tuscany this morning, and spend the morning at one of its historic gems: the walled city of Lucca. Join a local guide for an e-bike tour around the city’s well-preserved Renaissance walls. Continue along Nottolini’s Aqueduct along a lovely country cycle lane. After free time for lunch and exploring Lucca on your own, drive to the picturesque hills of Chianti.  Your home here is a delightful, family-owned agriturismo that produces its own organic wines and olive oils. This evening, sit down to a farm-to-table dinner featuring traditional Tuscan recipes made with produce from the farm. (B,D)

Biking: 10 miles (over 2 hours) with e-bikes, mostly flat terrain.

Day 8 — Chianti

Split into two groups for this morning’s activities: a vineyard tour and a cooking class. One group will set off with the trip leader on a walk in the vineyards, and then meet with a wine expert at the agriturismo to learn the steps of making wine. Take a wine cellar tour and enjoy a tasting—of the agriturismo’s wines and olive oils as well as locally produced cured meats and bruschetta. The group in the cooking class will learn from a local chef how to concoct a full Tuscan lunch, including handmade pasta, a traditional sauce, a main course, and a dessert. When the lunch is prepared, the two groups will gather to enjoy it on the terrace with views of the countryside and the farm’s own wines.  Later in the afternoon, set out on a leisurely hike through the vineyards to Certaldo. Ride the funicular to its charming medieval center, set high on a hilltop above the modern town, and walk its maze of streets with a local guide before dinner at a local restaurant. (B,L,D)

Walking: 1-2 miles, morning vineyard walk.  

Hiking: 3-4 miles afternoon hike; slight elevation gain through fields, vineyards, town streets.

Day 9 — Chianti / San Gimignano

Today the group will divide again to take a vineyard hike and wine cellar tour or participate in a cooking class. During free time after lunch, relax at the pool or go for a walk on your own. Then set out on excursion to the medieval hill town of San Gimignano, discovering the history and the secrets of this World Heritage site on a walking tour with a local guide. Celebrate your Italian sojourn tonight during a farewell dinner at a local restaurant. (B,L,D)

Hiking: 1-2 miles, morning vineyard walk.  

Walking: Afternoon walking tour, appromixately 2 hours.

Day 10 — Return Home

After breakfast, transfer to the airport in Florence for your flight home or extend your stay in Tuscany. (B)

Included meals are denoted as follows: Breakfast (B), Lunch (L), Reception (R), Dinner (D)

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