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Tuscany, Italy walking and hiking trips from Boundless Journeys

Italian Adventure

In Italy, culture is inescapable. At Boundless Journeys our specialty is turning the omnipresent into something personal and meaningful. Our Ancient Sicily Hiking tour showcases the largest island in the Mediterranean, guiding travelers from the castles of Erice to the Cathedral of Cefalù, from thought-provoking archeological sites to the serene beauty of an ancient vineyard. Our Tuscany & Umbria Walking transports you to a place where food, art, nature and life have been intertwined for thousands of years. Finally, the Hiking the Amalfi Coast & Capri offers the chance to see the majesty of Pompeii to the intimacy of a hands-on cooking class on the Sorrentine Peninsula. Regardless of which tour you choose, prepare yourself for a true Italian adventure.

Italy: Ancient Sicily Hiking

Fascinating ruins of early civilizations and beautiful coastal paths above the turquoise waters of the Mediterranean are ours to discover on this exploration of ancient Sicily.

$4,695 per person

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Italy: Tuscany & Umbria Walking

Wander your way through Italy's idyllic countryside, walking and hiking on ancient footpaths, sampling its finest food and wine along with its rural pace and way of life.

$4,495 per person, No Single Supplement*

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Italy: Hiking the Amalfi Coast & Capri

An ancient network of routes leads us across stunning landscapes, with abundant wildflowers and inspirational panoramas. The heritage of mule tracks lead us from village to village, where we are welcomed into local trattorias as friends. From the charming town of Ravello, to the picture perfect island of Capri, and the rugged Sorrento Peninsula, nature and architecture combine to create a highly evocative atmosphere.

$4,495 per person

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Latest Blog Posts About Italy

For Your Valentine: Three Exciting Adventures for Two

Happy Valentines Day, from all of us at Boundless Journeys! Be it a far-flung tropical paradise or a luxurious safari in the heart of Southern Africa, there’s no better way to celebrate the most romantic of holidays than by having a special adventure with the one you love.

Secret Amalfi: Unlocking Italy’s Seaside Treasure

Every summer people pack the Amalfi Coast’s winding cobblestone streets and rocky beaches. But there is a way to avoid the madness: visit in May or September, when beautiful weather prevails and the crowds have departed.

Stay at a Boutique Farmhouse on Boundless Journeys’ Ancient Sicily Tour

The food, wine, sea, countryside and ancient archeological sites of Southern Sicily make the boutique hotel La Foresteria the perfect place in which to experience all the very best of the island, both past and present.

Tales from the Trail – Italy: Ancient Sicily

Ahhhh . . . Sicily. I had the pleasure of joining a Boundless Journeys tour to Sicily just a couple of weeks ago. Truly unforgettable moments are now ingrained on my mind as I dream of the incredible pastries we enjoyed, the immense archeological sites we visited, the countryside walks with breathtaking views of the […]

A Day in Tuscany

Many times we are asked to describe a typical day on one of our trips. This is truly a difficult request as our trips are often filled with what our Italian guide calls “UPS’s” or unplanned surprises.

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