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

694 reviews

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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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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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Long weekend of whale watching with a WWF guide between the Amalfi Coast, Ischia and Capri

09/22/2025

Federica T.

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Italy

Great Captain! Thank you Rocco
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In the blue of Capri and the infinity of the Amalfi Coast

09/17/2025

Maria R.

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Switzerland

It was a wonderful experience. The skippers were great! Thanks to Captain Gianni and Robi - you were so nice! We saw some wonderful places. The boat could be cleaner. Anyway fabulous experience. Thank you all!

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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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