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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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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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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

684 reviews

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Weekend of sea and colors between Ischia, Procida and Vivara

06/29/2026

Manuela M.

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IT

Very nice experience, comfortable and clean boat, Gennaro the skipper a person always available and kind. Highly recommended!

Capri Light Blue - Two boats in company!

06/22/2026

LUDOVICA M.

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IT

Fantastic experience on board, in the company of skipper Francesco and his brother Alfredo. We celebrated our friend's bachelorette party with a view of the Faraglioni of Capri. The boat is very comfortable and spacious, it has everything you need to live intensely and comfortably every moment of your holiday. The kindness, professionalism and courtesy of the skippers allowed us to enjoy this moment of sharing with friends in a unique way! Pleasant navigation from Castellammare di Stabia, where you spend the first night, before embarking on the route to Capri. Here, in the roadstead, we had lunch, bathed and dived, reached the shore with the sup and also sang and danced. The Everything, surrounded by a breathtaking view. Super recommended experience, definitely we will be back!!

All-Inclusive Sailing: Capri, Positano, Amalfi

06/22/2026

Maria Grazia I.

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IT

They were enchanting days. Natural landscapes and enchanting locations. We filled our eyes with so much beauty, unforgettable baths and sunshine. Alessandro, the skipper, wonderful. With organization and skill he allowed us to make the most of the various days. And finally he prepared some really delicious menus to eat on the boat. To sum up :SUPER☺️

All-Inclusive Sailing: Capri, Positano, Amalfi

06/22/2026

Cinzia B.

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IT

June 2026 holiday, what can we say about this experience? Great everything Skipper Alessandro spoiled us for all three wonderful days

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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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