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

Discover more than 8 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

134 reviews

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La Flottiglia Mediterranea: Capri, Ischia, Procida e le isole Pontine

08/28/2025

Gloria G.

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Italy

Fantastic experience made special by the people we met on the boat and our skipper who made sure that the trip was 'carefree'! The flotilla is the right way to have fun and relax, sharing it with all the boats and personal moments with your sailing companions! In short, everything you need for a perfect holiday!
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La Flottiglia Mediterranea: Capri, Ischia, Procida e le isole Pontine

08/28/2025

Sara R.

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Italy

We had an unforgettable holiday at the Pontine Islands! The skipper Antonello proved to be truly exceptional: professional, competent and always attentive to safety, but also nice and helpful, which made the experience even more enjoyable. The islands are stunning, with hidden coves, crystal clear waters, and stunning sunsets. The boat was comfortable and well organized, perfect for experiencing the sea in total relaxation. Every day was a mix of adventure, discovery and moments of pure peace. I absolutely recommend this experience to anyone who wants to experience the Pontine from a unique perspective: thanks to Antonello we felt in excellent hands and we will take home precious memories.
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La Flottiglia Mediterranea: Capri, Ischia, Procida e le isole Pontine

08/28/2025

Sara R.

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Italy

We had an unforgettable holiday at the Pontine Islands! The skipper Antonello proved to be truly exceptional: professional, competent and always attentive to safety, but also nice and helpful, which made the experience even more enjoyable. The islands are stunning, with hidden coves, crystal clear waters, and stunning sunsets. The boat was comfortable and well organized, perfect for experiencing the sea in total relaxation. Every day was a mix of adventure, discovery and moments of pure peace. I absolutely recommend this experience to anyone who wants to experience the Pontine from a unique perspective: thanks to Antonello we felt in excellent hands and we will take home precious memories.
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An unforgettable week between Capri, Positano, Amalfi, Ischia, Procida...

08/27/2025

Antony S.

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Switzerland

Fabulous experience in such a nice area, Gennaro selected best places to surprise his guests during the journey. He is responsible, energized and attentive to our wellbeing. It was also great to meet smart people from different countries.

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