Tuscany and the Cinque Terre Walking Tour

Day 1: Florence

We meet in spectacular Florence and spend our first afternoon in the company of an art historian. While our guide tells us personal stories and historical anecdotes of the Medici family and others, we wind our way through the ancient streets—past towers, palaces, churches, the incredible dome designed by Brunelleschi, the landmark Ponte Vecchio and bustling Piazza Signoria. Late in the afternoon, we enjoy a last view of Florence before we head south across the Arno River into Chianti. A short journey leads us to our lovely hotel, an ancient villa originally constructed in the 13th century and surrounded by beautiful vineyards and enchanting villas that dot the nearby hills. Overnight: Chianti Meals: B, D

Day 2: Chianti / San Gimignano

Our morning walk takes us through vineyards and ends with an invitation to a private lunch with a local family in their charming country house on the grounds of a 15th century castle. Over lunch, we taste from our hosts’ cellar, enjoying a young Chianti Classico and a rich, aged “barrique” wine. 

Day 3: Chianti / Monteriggioni / Colle Val D'elsa

Following a breakfast of local specialties, we begin the day with a private visit to an 11th century Benedictine abbey that was an important medieval center for learning and a way station along the Pilgrims’ Road to Rome. Our explorations of the ancient complex precede a scenic walk to Monteriggioni, the most spectacular fortified village in all of Tuscany. Oval shaped with 14 towers placed evenly along its sheer walls, this remarkable fortress, today a bustling village, was built by Siena against Florence and was cited by Dante in his Inferno. Our footpath to Monteriggioni offers magnificent views of olive groves, stands of cypress and fields of poppies, and intersects sections of the Via Francigena. The ancient pathway was the principal route traveled by pilgrims on their way to Rome. In Monteriggioni, there is time for lunch, followed by a visit with a local artisan who still crafts terra cotta pots by hand. 

Day 4: Lucca / Santa Margherita

Heading north and west through Chianti and the Arno Valley, we arrive in Lucca for a visit and lunch. It was here in 56 BC that Caesar, Pompey and Crassus agreed to rule Rome as a triumvirate. It was also the first town in Tuscany to accept Christianity. Today, Lucca boasts wonderful 16th century Renaissance walls, a spectacular white marble duomo, Roman amphitheater and elegant shops situated on cobblestone streets. Join our local guide as we enjoy a short walk along a stretch of the Renaissance walls and through the historical center, then take some time on your own to explore some of the fine shops found in Lucca. 

Day 5: Cinque Terre

From our seaside hotel, we hop on the little coastal train for a quick and scenic journey to Rio Maggiore, the southernmost of the five coastal villages. Here, we join the Via dell’Amore walking trail, stopping for lunch in one of the villages and leaving plenty of time to enjoy a gelato and an espresso in another. Our walk today takes us through olive groves along cliffs overlooking the sea to the five sister villages: Manarola, Corniglia, Vernazza and finally Monterosso. (If you’d like to skip any of the walking, there’s always the coastal train and ferry boats that run between the villages.) 

Day 6: Portofino / Santa Margherita

This morning, we journey on foot right out of our hotel onto the Portofino Promontory, and follow a lovely path that leads us into the fabled coastal resort of Portofino for a visit. Here we have time to rummage the little shops that hug the picturesque harbor and even explore Castello Brown perched high above the village with scenic views of Portofino and the coastline. Midmorning, we walk out of Portofino on our way to St. Fruttuoso. The tiny monastery is located on a very small beach and is inaccessible by car. We reach the monastery via a beautiful, meandering path past villas tucked serenely behind flowering gardens and enjoy unparalleled views of the sea over the course of our walk of about two and a half hours. 

Day 7: Pisa

Leaving Santa Margherita we drive south to Pisa. Many of the Crusaders’ boats sailed from here, and the resulting Arabic art themes make its Duomo and leaning tower unique monuments. After a visit, you have the choice of parting company at the Pisa train station or airport, or even to transfer back to Florence with our guide. Meals: B