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

Discover more than 14 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.

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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

84 reviews

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From the Pontine to the Amalfi Coast by sailboat

07/14/2025

Anna P.

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Switzerland

Overall nice experience: beautiful places visited, good Skipper Leonardo, nice crew. Since this is the first time on this route, we have paid for the inefficiency of the organization in providing the right contacts in the various stages of navigation. In addition, there were problems with the tender that did not allow the whole crew to move freely in the various coves.
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Short sailing cruise in the Gulf of Naples

07/11/2025

Daniela D.

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Italy

My first experience on a sailing boat was an unforgettable experience, when the Universe puts the right people on your path at the right time. Every moment was intense, perfect and unforgettable, despite the rough sea, the change of tour due to the wind and the sea was all organized and managed calmly and with great professionalism and safety by Alessandro who was our skipper. Thank you for these three unforgettable days where we shared beautiful moments and the magic of being perfect strangers but immediately all old friends. A sensation never experienced. A gift like the breeze, the sun, the sea and the sense of touching freedom and embracing it totally.
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Capri LightBlue and Positano BluSKy

07/8/2025

Marianna D.

SUPER holiday!! Very good and very competent skipper! WONDERFUL travel companions! Places from 10elode!! To be repeated
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Capri LightBlue and Positano BluSKy

07/8/2025

Kaled E.

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Italy

My family and I have had a dream experience on a fantastic sailboat. Capri, Positano, Bagni della Regina, Li Galli, wonderful sites, waters of an indescribable blue. Gennaro as a skiper demonstrates a competence beyond any doubt, methodical, logical, didactic (he always offers an explanation of why and how to do it), always gentle, serene and attentive to any of our doubts or what we need. Impeccable and safe navigation. Our fellow travelers, as if we had known each other for a lifetime. Highly recommended, of course we will repeat.

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