Welcome to Tripping Sicily!

We believe that Sicily has an inestimable patrimony to impress your imagination, from awesome natural landscapes to ancient historical sites, traditional food and amazing wines. Once you land, you really take a step back into the whole history of the Mediterranean area, by travelling this magical territory.
If you are planning to visit Sicily you won’t regret it at all, a destination that suits to any traveler: couples, honeymooners, families, friends, special occasions and celebrations.
At Tripping Sicily we believe that customized experience is something that simply makes you feel special, and unique!

We are concierge for Private boat trip on luxury motor or sailing boats, exciting Jeep tours on top of Mount Etna, the highest active volcano in Europe, delicious Wine Tasting Trips to discover the best producers and learn more about the tradition of wine making in Sicily, the real Sicilian cooking class with local mammas or private chefs, immersed in flowering gardens after a walk in our traditional street food markets rich in colors and smells. These exquisites experiences are conceived thanks to a strong on the ground expertise and a pure passion for good and stylish living.

With us you can decide to book just a single experience or we can plan together your perfect Sicilian journey. Mail us your requests using the contact form and we’ll change your words into facts thanks to our qualified staff and a reliable network of partners from Syracuse to Catania, Taormina and the magical Aeolian Islands.

We want to unveil you different corners of this destination out of the beaten track, the pure essence of Sicily right besides local people for your once in a lifetime journey.

Benvenuti a Casa!

What Clients Says

Sicily Boat Rental

We design your Private Boat Cruise in Sicily from Taormina, Syracuse and the gorgeous Aeolian Islands. Different itineraries on board our top selection of Motor boats, Sailing Boats and Vintage Gullets. Let’s surf the Mediterranean in one day trip or long 7 days cruises with a dedicated concierge service to assist you during the whole journey. Book now your Sicilian experience by the sea.

Sicily Tour Experience

We’ve selected exquisite experiences to explore this marvelous territory. You can ascent Mount Etna with exciting Jeep Off Road excursions, enjoy a wine tasting trip through the history of Sicilian wine producers or immerse in the flavors of the Sicilian Cuisine participating to private cooking lessons in exclusive locations. Taste another Sicily! Book now the experiences to enrich your Sicilian journey with us!

Sicily Luxury Concierge

Our professional staff we’ll turn your wishes into a truly unforgettable experience. You can choose to have a complete trip planning service to design your full itinerary or you can ask for “A la carte” concierge service just to plan some elements of your trip. Complete now the contact form within all details about your suitable journey, we’ll reply in maximum 48h with suggestions on how we can arrange it for you.


The best of Sicily!

Give us the pleasure to show you this fantastic dimension!

More information?

E-Mail: info@trippingsicily.com
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