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Flotilla yacht sailing holidays & tours in Italy

Discover the magic of flotilla sailing holidays in Italy! A new way of traveling with your loved one, your friends or your family. Find your dream adventure among hundreds of holidays organised by local skippers.

Why book a holiday with Sailsquare?

The world's largest marketplace for sailing holidays

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 - Flotilla yacht sailing holidays & tours in Italy

1719 reviews

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La Flottiglia Mediterranea: Capri, Ischia, Procida e le isole Pontine

09/23/2025

Ciro S.

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Italy

The flotilla holiday was an unforgettable experience, made special not only by the wonderful places we visited, but above all by the people who were part of it. Thanks to our skipper Gianfilippo, always attentive, competent and able to convey safety and serenity to the entire crew of the Duca del Sale. Together with him, thanks also go to Vladimiro and Antonello, skippers of Nora and Ludi respectively, the other two boats. A round of applause to Alessio and to the whole organization of the flotilla, who with professionalism and availability made everything smooth and pleasant. The itinerary, the activities and the management of every detail really made the difference. The team spirit that was created between the boats was also beautiful: we played, danced, ate and laughed together, turning every day into a precious memory. A unique atmosphere was established, made up of sharing, friendship and fun. An experience that I recommend to anyone who wants to experience the sea in an authentic, convivial and unforgettable way. Thank you all, we will see you again soon at sea. Fair winds!
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The Wild Flotilla: dive into the wild nature of Tuscany and Corsica

09/15/2025

Giulia P.

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Italy

Four boats, two islands, a family: a few points to sum up one of the most beautiful holidays ever. Dinners at anchor under the stars, aperitifs at sunset, naps under the sun. But also coves and wild beaches, sperm whales and unexpected "wild". On board, a lot of sharing that, from the beginning, led us to bond with each other and to make us feel, right from the start, friends since always. A unique experience to experience the sea in a memorable way.
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The Wild Flotilla: dive into the wild nature of Tuscany and Corsica

09/14/2025

Domenico B.

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Italy

Nice tour, great organization and good company... The right compromise between relaxation and social life
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Flottiglia Different: Party e nuovi amici alle isole Eolie

09/11/2025

Eleonora N.

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United Kingdom

It's not the first holiday with Different Sailing, and it never disappoints! Mix of fun and relaxation! Everything organized great, as always! Super recommended holiday!

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