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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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4.8

All Inclusive Tour: Capri, Amalfi, Cetara, e Sorrento

Italy: Naples & Amalfi Coast

5 days - 5 nights

2 departures available

August - September

€1,150

Per person

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4.7

Amazing Capri and Amalfi Coast on a sailboat

Italy: Naples & Amalfi Coast

4 days - 3 nights

One departure available

July - August

€524

Per person

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5.0

Capri, Sorrento, Positano and Amalfi by Catamaran

Italy: Naples & Amalfi Coast

5 days - 4 nights

One departure available

September

€645

€581

Per person

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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

701 reviews

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June 2nd long weekend between Procida, Ischia and Ventotene

06/6/2026

Valentina G.

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IT

Really nice long weekend of the second of June, well-kept and comfortable boat and group with which we immediately created harmony, also thanks to Umberto, a nice, prepared skipper and a great connoisseur of the places, who organized everything with care, always making us feel at home

June 2nd long weekend: discovering Capri, Ischia and Procida

06/4/2026

Ivana G.

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IT

Very comfortable, spacious and clean sailboat. Gennaro proved to be a nice and helpful skipper, helping to make the experience on board pleasant, and also participating in land trips. Less convincing, however, was the management of the itinerary: the moorings were often far from the coast, even with favorable weather conditions, and the stops did not allow you to explore exclusive places that could only be reached by sea. Furthermore, despite being part of the program, the tender was never used, limiting the possibilities of visiting coves and more hidden areas. Overall, a relaxing and pleasant experience, but below expectations in terms of exploration and itinerary, considering that the context would have allowed it.
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Capri Light Blue - Two boats in company!

06/4/2026

Christian C.

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IT

It's not the first trip I've made with SailSquare, but I can say without hesitation that this was one of the most beautiful experiences I've had so far. Gennaro is an extraordinary skipper and owner: he combines great technical expertise and deep sea experience with a rare ability to put everyone at ease. Always serene, helpful, never tense, always attentive to the safety and harmony of the group. He is one of those people who convey trust from the first moment and with whom it is pleasant to share time, conversations and emotions. Thanks to him we spent unforgettable days, sailing in total safety but above all in an atmosphere of authentic conviviality. On her boat you feel like guests, not customers: it is cared for in every detail, welcoming, full of comfort and attention that make you feel how much it is loved and lived by those who drive it. I take home wonderful views, new friendships and memories that will last a long time. A heartfelt thank you to Gennaro for the passion, culture, humanity and elegance with which he accompanied us in this experience. I really hope to be back on board his boat soon.
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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!!

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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

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