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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

719 reviews

Capri, Sorrento, Positano and Amalfi by Catamaran

09/16/2026

Marco B.

Recommended experience

The gems of the Amalfi Coast: Capri Light Blue, Positano Blue Sky, Amalfi Dreaming History

09/14/2026

Dali G.

-

FR

Comfortable boat, serious skipper, lovely hostess, beautiful destination!
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The gems of the Amalfi Coast: Capri Light Blue, Positano Blue Sky, Amalfi Dreaming History

09/14/2026

CARMINE R.

-

IT

Great organization
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Seven days not only on the Amalfi Coast

09/10/2026

antonella a.

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IT

Lovely week on the boat. The organization was impeccable: every detail, from the timing to the activities, was carefully studied and with a professional and welcoming management. The proposed itinerary is exceptional: hidden bays, crystal clear waters, well-selected moorings even when the sea has forced us to change course. This is thanks to the skipper's extraordinary knowledge of the places, who guided us as only those who really live the sea can do. Each stage had a meaning, a rhythm, an emotion. The care for the crew was total, at 360 degrees. Comfort on the boat always at the top thanks to its large size, relaxed but also dynamic atmosphere, never boring. And when you went ashore, the entertainment was always calibrated: the right venue, the right time, the right mood. In short, I didn't take a boat holiday, but I did the boat holiday, the one that also changes the way you look at the sea and experience your land. An experience that stays with you, do it!

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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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