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Whole boat with skipper yacht sailing holidays & tours in Naples & Amalfi Coast

Discover more than 5 opportunities to get on board a Whole boat with skipper adventure in Naples & Amalfi Coast. A unique experience with a local skipper, starting at €350 a week.

Why book a holiday with Sailsquare?

The world's largest marketplace for sailing holidays

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 - Whole boat with skipper yacht sailing holidays & tours in Naples & Amalfi Coast

142 reviews

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Capri LightBlue and Positano BluSKy

09/16/2025

Claudia D.

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Italy

We have just returned from a beautiful holiday that allowed us to visit wonderful places with a convenient and comfortable boat; Gennaro, was a skipper who was always friendly and attentive to all our needs, he showed great ability and experience even in solving small unforeseen events; definitely to be repeated!!
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Capri LightBlue and Positano BluSKy

09/14/2025

Maurizio G.

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Italy

Everything went well prepared skipper helpful and nice beautiful Capri beautiful
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La Flottiglia Mediterranea: Capri, Ischia, Procida e le isole Pontine

09/10/2025

Francesco S.

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Italy

It was not a simple holiday. It was a symphony of wind and sea, thanks to "La Flottiglia" which turned my first sailing holiday into a fantastic experience. Almost every night we spent in the middle of the blue, far from the ports and close to the essence of freedom. Sleeping under the stacks of Capri was something unique: the calm sea, the stars above us and the silence that makes you really feel part of that landscape. We visited wonderful islands: Capri, Ischia, Procida, Ventotene, Ponza and Palmarola. Each one has given us something different, including colors, landscapes and unforgettable moments. The evening at the Terraces in Ponza was one of the funniest! The catamaran parties were super fun, and getting to know the people from the other boats made it even more interesting. Each with its own story, its own spirit, and a great desire to have fun. If I could, I would go back tomorrow. In fact, I wouldn't have gotten off the boat at all!
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Capri LightBlue and Positano BluSKy

09/10/2025

DANIELE R.

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Italy

Beautiful weekend with a very pleasant crew... Precise skipper and perfect boat: clean, comfortable and spacious... Gennaro is a very prepared, helpful and nice skipper!! He guided us in a punctual and clear way and made us become familiar with the activities of the boat!! He was able to create a good atmosphere right from the start!! The "breakfast at dawn with a view of the Faraglioni of Capri" is a moment that is "priceless"... Really a good experience, thank you all until next time!!

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