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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.

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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

228 reviews

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Weekend of sea and colors between Ischia, Procida, Vivara and the Phlegraean fields

10/10/2023

Giuseppe B.

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Italy

Weekend fantastico Gennaro skipper professionale attento e aggregante è riuscito formare un gruppo di compagni di viaggio fantastici Le sue informazioni sul link ricevuto alla prenotazione erano perfette esaustive e aggiornate Tornerò presto Grazie a tutti
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Capri LightBlue weekend

10/6/2023

Gigia T.

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United Kingdom

Gennaro è stato un capitano fantastico! ci ha fatto divertire nella splendida capri. ci ha mostrato posti che solo un vero lupo di mare come lui poteva! Super esperto e super disponibile. al rientro abbiamo dimenticato una cassa audio a bordo e prontamente l ha impacchettata e spedita a casa nostra! grazie gennaro!!!
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Weekend of sea and colors between Ischia, Procida, Vivara and the Phlegraean fields

10/2/2023

Alessio G.

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Italy

Finalmente la mia prima esperienza in barca a vela ‘fantastica’ è l’aggettivo giusto per descriverla. Barca stupenda, dotata di tutti i confort, pulita e ordinata. Itinerario organizzato nei minimi dettagli. Emiliano skipper attento, esperto e simpatico. Non potevo chiedere di meglio!!!
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The Mediterranean Flotilla: Capri, Ischia, Procida and the Pontine Islands in CATAMARAN

09/27/2023

Giulia P.

Inizierei con un"CHE MERAVIGLIA LA FLOTTIGLIA!".Il mio viaggio in catamarano è stato un'esperienza emozionante e indimenticabile.Partire con un gruppo di 10sconosciuti poteva sembrare intimidatorio all'inizio ma si è rivelato essere un'avventura straordinaria.Il primo impatto con il catamarano è stato a dir poco WOW.Il nostro skipper, Andrea,ha subito creato un'atmosfera accogliente e la sua conoscenza del mare e delle isole che stavamo per visitare ha reso il viaggio ancora più interessante.Abbiamo visitato isole meravigliose esplorando baie e spiagge ma anche scendendo a terra ogni giorno.Le giornate a bordo erano piene di risate, chiacchiere e brindisi no stop.Nonostante fossimo un gruppo di estranei all'inizio,abbiamo rapidamente legato, condiviso esperienze e storie di vita sotto cieli stellati. Difficile spiegarlo a parole.è stata più di una vacanza.Grazie Andrea per averci accompagnato e grazie La Flottiglia per queste giornate meravigliose che conserverò per sempre nel cuore.

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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

Amalfi Coast: the best travel ideas

Other travel ideas

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