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Sport & wellness yacht sailing holidays & tours in Italy

Discover more than 9 opportunities to get on board a Sport & wellness adventure in Italy. A unique experience with a local skipper, starting at €350 a week.

Why book a holiday with Sailsquare?

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The world's largest marketplace for sailing holidays

80,000 travellers have already chosen their holiday from a catalogue of 12,000 proposals in 120 destinations, worldwide.

Get onboard solo, with your family or your friends

Get onboard solo, with your family or your friends

Book a single spot, a cabin or the whole boat just for yourself, or for your friends or family.

Find out before you book who's waiting for you on board

Find out before you book who's waiting for you on board

Find out more about the skipper and travellers who have already booked the holiday, to find out more about the

Sailing holidays that suit all budgets

Sailing holidays that suit all budgets

On Sailsquare, sailing holidays are within everyone's reach. Thousands of proposals to choose from, at affordable prices.

Reviews - Sport & wellness yacht sailing holidays & tours in Italy

750 reviews

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Long weekend of whale watching with WWF guide on an 18-meter schooner

10/2/2025

Marco C.

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Italy

Unforgettable experience aboard the Schooner Mahayana. An essential and shared life on board. Thanks to Captain Francesco, his crew and WWF guide Ilaria, a serene and pleasant atmosphere was established with all guests from the beginning. Browsing great places. Educational experience on the marine environment with a focus on cetaceans and environmental impact. As a first experience we particularly appreciated the pace of navigation, the life on board and the company.
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Weekend a Capraia, trekking e natura

09/30/2025

Andrea B.

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Italy

Valid skipper, experience not in accordance with the program Sailing and trekking (no trekking) requests for extra contributions not reported
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Cous cous Festival in San Vito lo Capo and the Egadi Islands

09/29/2025

Lara P.

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Italy

A beautiful trip around the Egadi Islands with combined couscous festival. A round of applause to the skippers Giangiacomo, mine, and Mario on the sister boat. They led us in the loop, carefully and prudently, but without ever letting us miss anything! They were attentive to the different needs of their crews, with professionalism and discretion!
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Long weekend of whale watching with a WWF guide between the Amalfi Coast, Ischia and Capri

09/28/2025

Valerie D.

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France

Very nice experience, the boat is comfortable, the whole group was kind. Every day Ilaria made us aware of the life and environment of cetaceans, and their preservation. It was instructive. Rocco is a captain like no other! Very professional, you feel totally safe. Observation, anchoring in the port, swimming... A very good time out of time! Thank you to Rocco, Ilaria, and the other participants for this moment and their kindnesses.

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