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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.

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 - Yacht sailing holidays & skippered tours in the Gulf of Naples and Amalfi Coast

617 reviews

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In the blue of Capri and the infinity of the Amalfi Coast

07/8/2025

Laura D.

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Italy

È stata un'esperienza molto piacevole, siamo stati fortunati perché il gruppo ha funzionato bene da subito. Le destinazioni non necessitano di commenti: sono posti incantevoli! Lo skipper Gennaro ci ha accuditi e ci ha fatti sentire rilassati e al sicuro. Esperienza consigliata per vivere il mare nel suo pieno senso e in tutta la sua bellezza
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Capri LightBlue and Positano BluSKy

07/8/2025

Kaled E.

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Italy

Mi familia y yo hemos vivido una experiencia de ensueño en un velero fantástico. Capri, Positano, Bagni della Regina, Li Galli, sitios estupendos, aguas de un azul indescriptible. Gennaro como skiper demuestra una competencia más allá de cualquier duda, metódico, lógico, didáctico (siempre ofrece una explicación del porqué y de como hacerlo), siempre gentil, sereno y atento de cualquiera de nuestras dudas o de lo que necesitáramos. Una navegación impecable y segura. Nuestros compañeros de viaje, como si nos conocieramos de una vida. Altamente recomendada, por supuesto que repetiremos.
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In the blue of Capri and the infinity of the Amalfi Coast

07/7/2025

Claudia D.

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Italy

Tutto super!
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Capri LightBlue and Positano BluSKy

07/7/2025

Francesco L.

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Italy

Esperienza meravigliosa, skipper impeccabile nella sua disponibilità, compagnia super. Assolutamente da ripetere

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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

Naples & Amalfi Coast: the best travel ideas

Other travel ideas

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