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Sail to Sicily in a Private Villa at Sea

by Felicity Long

Jan 21, 2020

Sicily. Photo Credit: The Thinking Traveller


Ever wish you could have a private villa experience at sea? Now you can thanks to The Thinking Traveller, a New York- and London-based holiday rental company which manages more than 200 exclusive villas in the Mediterranean.


The company decided to take to the sea in July 2020 by adding a Family Sailing, a lavish, all-inclusive, fully catered family holiday to the Aeolian Islands in Sicily.


Family Sailing. Photo: The Thinking Traveller


The voyage will set sail for Vulcano, Lipari, Panarea and Salina, anchoring in some of the Mediterranean’s most glamorous islands, including Stromboli, considered by many the most spectacular of the Aeolian Islands.


Specifically designed for families and friends with children, multigenerational travelers or groups of friends, the Family Sailing by The Thinking Traveller sails aboard two skippered catamaran-style yachts with a total of nine cabins for up to 18 people.


Family Sailing. Photo: The Thinking Traveller


Guests are greeted with welcome kits stuffed with beach towels, sarongs, sunscreen, certified life jackets, snorkeling equipment and more.


Children in Sicily. Photo Credit: The Thinking Traveller

Traveling with little ones? Kids aged 5 and older are entertained on their own dedicated Kids Club monohull yacht, helmed by an experienced skipper and activity leader, while guests of any age will have the services of a host/chef.


Family Sailing, Aeolian Islands. Photo: The Thinking Traveller


The Kids Club activity leader will tailor the week’s activities to the ages and preferences of the children. Learning to sail takes front and center for kids, who will have a chance to “learn the ropes” during the week. Other activities include snorkeling, hiking up volcanoes, treasure hunts, picnics, water sports, stargazing and evening sing-a-longs on the beach.

Family Sailing, Aeolian Islands. Photo: The Thinking Traveller


Meanwhile, adults can enjoy an evening ascent of Stromboli with an expert guide; discover the archaeological site of Lipari; visit the vineyards of Salina for a wine tasting tour; savor Aeolian cuisine at a Michelin-starred restaurant; try one of Vulcano’s sulfur spas; or hike up to the volcano’s crater. The flexible itinerary can be adapted to the group’s preferences.


Families with a little extra time can book the sailing experience as a pre- or post-trip add-on to a stay at one of The Thinking Traveller’s villas in Sicily, such as Casa Vera in Noto or La Prora in Taormina.


Bookable exclusively through The Thinking Traveller, the luxe sailing holiday is available for a seven- or 14-day cruise, July 4–18.


Family Sailing, Aeolian Islands. Photo: The Thinking Traveller


The $65,000-per-week price tag includes boat rental, crew, six breakfasts, six lunches and three dinners on board, as well as daily refreshments, daily maid service, port and fuel taxes, excursion planning and organized daytime activities in the Kids Club.


Family Sailing, Panarea, Sicily. Photo: The Thinking Traveller


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