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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

612 reviews

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Short sailing cruise in the Gulf of Naples

07/5/2025

francesca s.

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Italy

Esperienza gratificante un ottimo inizio estate, luoghi incantevoli e compagnia piacevolissima
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All Inclusive Tour: Capri, Amalfi, Cetara, and Sorrento

07/5/2025

MANJA B.

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Slovenia

The whole trip was great in every way. Alessandro spoiled us by cooking lunches, preparing snacks and making coffee whenever we felt like it! We saw all the planned places/towns and enjoyed every moment on deck and in the sea:)
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Weekend of sea and colors between Ischia, Procida and Vivara

07/1/2025

Lucia M.

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Italy

Primo weeekend trascorso in barca a vela con Spasso a vela, sotto consiglio della mia amica, ed è stata un’esperienza unica! Lo skipper Emiliano e la sua fantastica moglie Ida hanno reso l’intero weekend rilassante e divertente facendoci scoprire le bellezze di Ischia e Procida e calette sconosciute dai turisti ma veri e propri angoli di paradiso! SUPER CONSIGLIATO e sicuramente io e la mia amica torneremo il prossimo anno per una nuova avventura 😝
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Weekend of sea and colors between Ischia, Procida and Vivara

07/1/2025

Floriana S.

Reduce dall esperienza fantastica dell anno scorso, anche quest'anno ho prenotato un weekend in barca a vela con Spasso a vela. Emiliano si conferma una garanzia, professionalità e calma fanno di lui lo skipper perfetto, quest'anno ho avuto la fortuna di conoscere anche la sua fantastica moglie Ida, che dal primo istante mi è entrata nel cuore con la sua dolcezza e allegria. Un weekend indimenticabile, mare da sogno, relax e divertimento garantito. Io e la mia amica (con cui sono partita) abbiamo lasciato un pezzettino di cuore su quella barca. Spero di ritornarci anche il prossimo anno

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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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