Tuscany on Foot

We gather in Toronto for our overnight flight to Rome, Italy.

Upon arrival in Rome, we are welcomed by our national guide. We travel north along the Apennine mountain range toward the renowned spa centre and hill town of Montecatini Terme. Tonight, we gather for our welcome reception and dinner. 

Hotel Columbia Wellness & Spa - 6 nights 

Our private coach transports us to the Florence area, setting the stage for an unforgettable walking adventure as we trek across the scenic hills of Fiesole along the Arno Valley down into Florence. Next, we enjoy the afternoon at leisure in Florence, the cradle of the Renaissance, before returning to Montecatini for dinner. 

Walking time: 2 hrs
 

Today, our walk begins at Colle di Val d’Elsa, taking us through scenic vineyards and woods to a charming garden restaurant. Here, we enjoy a rustic meal featuring crostini, various types of pasta and wine. Afterwards, we travel by coach to San Gimignano, where striking medieval towers built by rival merchant families still stand today, earning the town its famous nickname, “Town of Fine Towers”. During our free time, we can visit one of the most renowned ice cream parlours in Tuscany before returning to Montecatini. 
 

Walking time: 3 hrs

This morning, we drive to the world-famous Chianti Classico wine region, where our walking journey takes us from the picturesque wine village of Greve through lush forests and past rolling vineyards to one of the area’s historic world-class wineries. Following an exclusive tour of the centuries-old wine cellars, we gather for a traditional wine-grower’s lunch featuring homemade sausages and other savoury ham specialties, accompanied by our choice of excellent regional wines before we return to Montecatini for dinner. 

Walking time: 3 hrs 
 

Setting out across the rolling hills of Montalbano, we make our way past scenic olive groves and vineyards toward Vinci, the hometown of history’s most renowned genius, Leonardo da Vinci. Our path leads us to his picturesque birthplace and on to a local vineyard and olive oil farm, where we enjoy lunch accompanied by regional wine tastings led by a sommelier. In the afternoon, we take a short stroll from the village of San Baronto to our host Christian’s home for wine and appetizers before returning to Montecatini. 

Walking time: 1.5 hrs

Venturing across the rolling hills surrounding the historic village of Montecarlo, we pause for a delightful lunch served in an old farmhouse featuring exceptional local cuisine and fine wines. elegant boutiques or sip a warm cappuccino at a cozy street café before returning to Montecatini. 

Walking time: 1.5 hrs

Saying goodbye to Montecatini Terme, we travel west toward Pisa for a quintessential Tuscan experience at the legendary Piazza dei Miracoli, home to the iconic Leaning Tower. After a brief visit, we continue down the scenic Tyrrhenian coast, heading south to Castiglione della Pescaia, widely regarded as the most beautiful seaside resort in the region. 

Hotel L’Approdo - 6 nights

Stepping into Maremma Regional Park, we explore a protected natural landscape rich in flora and fauna. Afterwards, we transfer to a quaint medieval town to enjoy a traditional lunch featuring authentic local specialties like homemade pasta and savoury wild boar stew. We then return to Castiglione with the rest of the day at leisure to explore the beautiful seaside town. 
 

Walking time: 3 hrs
 

We set out along ancient pathways between the historic towns of Sovana and Pitigliano, communities that once flourished during Etruscan times and later evolved into powerful medieval republics. Enjoy a packed lunch along the way, followed by free time in the afternoon to wander the area before returning to Castiglione. 

Walking time: 2.5 hrs

A short coach ride brings us to the lively port of Piombino, where we board a ferry bound for Elba Island, the jewel of the Tuscan Archipelago. On arrival, we explore the island on a guided coach tour, pausing at spectacular lookouts and storied historic sites. Later in the afternoon, we sail back across the shimmering sea and return to Castiglione. 

This day is entirely ours to relax and unwind. We might take advantage of our hotel’s wonderful amenities, stroll along the nearby beach, or venture out independently to discover the area’s charming corners.

For our last hiking day, we set out on our most ambitious route yet, saving one of the region’s most breathtaking landscapes for the finale. Our trail traces the edge of the tranquil Orbetello Lagoon toward Monte Argentario, a dramatic rocky promontory that once stood alone in the Tuscan Archipelago and is now connected to the mainland by two narrow strips of dune. We make our way to the picturesque fishing port of Porto Ercole, guarded by three fortresses, to explore briefly before we head to a seaside restaurant for a feast of fresh local fish. Later, we continue to the stylish harbour town of Porto Santo Stefano to stroll at leisure. In the evening, we return to Castiglione to celebrate the close of our Tuscan walking journey with a festive farewell dinner. 

Walking time: 3.5 hrs
 

We transfer to the airport this morning for our return flights to Canada, bidding farewell to Tuscany.