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Sailboat yacht sailing holidays & tours in Naples & Amalfi Coast

Discover more than 6 opportunities to get on board a Sailboat 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 - Sailboat yacht sailing holidays & tours in Naples & Amalfi Coast

637 reviews

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

08/30/2025

VANIA C.

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Italy

A week of vacation lived splendidly in excellent company. A mix of relaxation and adventure that gave rise to pure fun. The super professional Skipper Gianfilippo managed to tame and excite the whole group. The only observation to the organization: I would check the sheets provided. Many were worn out.
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La Flottiglia Mediterranea: Capri, Ischia, Procida e le isole Pontine

08/30/2025

Ettore P.

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Italy

Beautiful experience, great company, too bad for the breakage of the windlass on Thursday which compromised the freedom of movement of the last 2 days! For the rest, a holiday to be recommended to those who want freedom, fun and lightheartedness combined with the curiosity of new acquaintances!!
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La Flottiglia Mediterranea: Capri, Ischia, Procida e le isole Pontine

08/30/2025

Sara L.

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Italy

Beautiful experience! I'm already planning the next one!
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La Flottiglia Mediterranea: Capri, Ischia, Procida e le isole Pontine

08/30/2025

Roberta C.

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Italy

Great potential but we need a coordinator for the ashore outings and more logistical assistance for the galley

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