Group members gather in Toronto for the transatlantic overnight flight to Rome, Italy.

Upon arrival in Rome, our national guide will greet us and accompany us throughout our journey until we return home. We will venture north along the picturesque Appenin Mountain range to the popular hill town and spa centre of Montecatini Terme. This evening, enjoy our welcome reception and dinner at our hotel which is centrally located and has exceptional spa facilities. Hotel Columbia (6 nights) 

Our coach will bring us to the Florence area today, where we will hike on top of the hills from Fiesole along the Arno Valley down into Florence. Enjoy lunch on your own in the old town with choices from traditional Florentine menus. Spend the afternoon on your own in the cradle of the Renaissance, a fountainhead of genius, and still one of the art world’s most prestigious cities. Return to Montecatini for dinner and overnight. (2 hours hiking)

Embark on a scenic hike from Colle di Val d'Elsa, passing through vineyards and wooded areas until we reach a charming garden restaurant. Here, we’ll enjoy a  rustic meal with crostini and various types of pasta, wine, and water. For those interested, there will be various draft beers on tap (optional).  Travelling by bus, we continue down a busy road to reach our destination of San Gimignano. In medieval times, each merchant family built its own fortress tower and residential area. Many still remain today, hence the nickname “Town of the Fine Towers.” Free time in San Gimignano provides you with the chance to visit the most famous ice cream parlour in all of Tuscany. Later we return to Montecatini. (3 hours hiking)

We drive to the world-famous Chianti Classico wine region. Our hike takes us from the picturesque wine village of Greve in Chiani through the wonderful landscapes of central Tuscany, through forests, and past vineyards to another world-class winery called Verrazzano. After a tour of the centuries-old wine cellars, we will have a traditional wine-grower’s lunch, featuring homemade sausages and other ham specialties. Of course, we will also have our choice of excellent wines. Return to Montecatini for dinner. (3 hours hiking) 

Walk along the low Montalbano mountain range through olive groves and vineyards. We start in Vinci, the hometown of the world-renowned genius, Leonardo da Vinci. Our path takes us to his picturesque birthplace where we’ll stop at a vineyard and olive oil mill. During a traditional oil farmer’s lunch, a specially appointed sommelier will familiarize us with all of the different types of wines we’ll be served. In the afternoon, we’ll take a short walk from the small village of San Baronto to an Italian Villa for some wine and appetizers. Back to Montecatini. (4 hours hiking)

Today we hike around the hills of the wine village of Montecarlo. Lunch will be in an old farmhouse with excellent cuisine and wines. After we’ll visit the well-known art city of Lucca with free time for shopping in the many elegant boutiques or perhaps a cappuccino in a cozy café before we return to Montecatini. (2.5 hours hiking)

After bidding farewell to Montecatini Terme and we drive west in the direction of Pisa. Visit the Piazza dei Miracoli, or “Miracle Square,” where the Leaning Tower is a must see in Tuscany. After a brief stop, we’ll continue along the coast of the Tyrrhenian Sea, driving south to Castiglione della Pescaia, likely the most beautiful seaside village in Tuscany. Tonight we enjoy a cocktail and a dinner of local dishes. Hotel L’Approdo (6 nights) 

During today’s hike we will explore the Natural Park of Maremma, a completely untouched area with rich, unspoiled flora and fauna. Afterwards, we transfer to a small medieval town for lunch at a traditional Maremma restaurant featuring local cuisines like homemade pasta, wild boar stew, and more. We return to Castiglione with free time to explore the beautiful city. (3 hours hiking)

Hike between the towns of Sovana and Pitigliano, both of which were important in Etruscan times and went on to become powerful republics in the Middle Ages. Enjoy a packed lunch and free time in Pitigliano to explore before returning to Castiglione. (2.5 hours hiking)

Travel by bus to the port of Piombino where we board a ferry to the Island of Elba, which is the most important of all the Tuscan islands. During our journey, we will take a brief bus tour of the island and make several stops along the way. Finally, we will return to Castiglione in the afternoon.

Today has been left completely free to enjoy our hotel’s amenities, unwind on the beach, or head out and explore the beautiful seaside village.

For our last hiking day, we have chosen a spectacular area and an ambitious route. We’ll walk along the Lagoon of Orbetello down to Monte Argentario. Originally part of the Tuscan archipelago, Monte Argentario’s rocky massif is now connected to the mainland by two dunes. Our main destination is the historic port village of Porto Ercole with its three fortifications. After a short visit, our bus will bring us to a restaurant with select local fish specialties. At the end of our journey, we drive to the elegant, main town of Porto San Stefano for free time. Back in Castiglione we gather for our farewell dinner. (3.5 hours hiking)