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Yacht sailing holidays & skippered tours in the Gulf of Naples and Amalfi Coast

Whether it is for a weekend of good food, good sea and sweet life, or for a longer trip to discover the beauty of southern Italy, the Italy, sailing vacations in Ischia, Capri, Procida and the other pearls of the Gulf of Naples the other pearls of the Gulf of Naples know how to surprise everyone.

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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

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

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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

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

Reviews - Yacht sailing holidays & skippered tours in the Gulf of Naples and Amalfi Coast

698 reviews

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In the blue of Capri and the infinity of the Amalfi Coast

05/30/2026

Alessandra C.

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IT

Beautiful experience, very pleasant crew. Gennaro really made a difference both for his experience but also for his kindness! Highly recommended!!

In the blue of Capri and the infinity of the Amalfi Coast

05/30/2026

Vincenzo D.

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IT

For us it was the first experience on a sailing boat and it couldn't have gone better. In our opinion, behind the experience, there are the people: Gennaro, the skipper, was the real wild card as well as the glue of this magnificent weekend. An exquisite person. We couldn't have wished for anything better. A guy (I hope he won't be offended) with whom every chat was constructive and full of ideas. Furthermore, to end on a high note, a further point of awareness that I took home is that thanks to him and this adventure I decided to want to obtain my boat license soon. We highly recommend this lifetime experience!

In the blue of Capri and the infinity of the Amalfi Coast

05/26/2026

Roberto L.

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IT

A great weekend! Beautiful places visited, particular attention was paid to organizing the tour in maximum safety in navigation and in maximum comfort. The skipper Gennaro is very prepared, a well-equipped boat, very comfortable and externally clean. Highly recommended
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In the blue of Capri and the infinity of the Amalfi Coast

05/26/2026

Ludovica L.

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IT

Weekend on the coast on a sailing boat?! Totally worth it! Beautiful experience!

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Guides & tips


Amalfi Coast

Positano, Amalfi and Cetara are just some of the best destinations for a sailing or catamaran holiday in the Gulf of Naples.
Guide to the Amalfi Coast on a sailing boat

Capri, Ischia and Procida

Enchanted landscapes and elegant haunts, thermal springs and seabeds full of surprises, simplicity and glamour: there is more than one reason to choose these timeless islands as a destination for a yachting holiday in stages.
Guide to Capri, Ischia and Procida on a sailing boat

Italy

Tuscany, Sardinia, the Aeolian Islands and Liguria are just some of the most beautiful destinations for a sailing or catamaran holiday, let's discover them all!
Guide to Italy on a sailing boat

Catamaran vacations

An alternative to the sailboat, the catamaran is an ideal choice for those who do not want to give up comfort and convenience and for a first vacation at sea.
Guide to the catamaran vacations

Singles and solo travellers

Set out alone and return enriched by an unparalleled baggage of freedom, new friendships and lasting bonds. It is on a sailboat that an adventure as a solo traveler turns into a unique sharing experience.
Guide to solo travellers sailing holidays

Sailing vacations for families

To leave with one's family and return home enriched by an unparalleled baggage of adventure, bonds and indelible memories.
What to know before you go sailing with your family?

Sailing with children

Have you ever wondered if there is a vacation that is both the best for children and parents? The answer is yes, and it is indeed on a sailboat!
uide to sailing vacations with children

Naples & Amalfi Coast: the best travel ideas

Other travel ideas

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