header cover
logo

Log in

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

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

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 more about the skipper and travellers who have already booked the holiday, to find out more about the

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

708 reviews

Capri Light Blue - Two boats in company!

06/16/2026

Giovanni D.

-

IT

Fantastic experience also thanks to the sympathy and professionalism of Gennaro and his team

Weekend of sea and colors between Ischia, Procida and Vivara

06/15/2026

Vladimiro L.

-

IT

The boat was perfect, very well maintained and with everything you need to enjoy total relaxation. We had a lot of fun, including swimming in beautiful places, great company and that atmosphere that only life on a boat can give. The real added value, however, was our skipper, Emiliano. She was the right person in the right place: professional, super helpful and able to make us feel immediately at ease, always with a smile and a joke ready. He made us discover wonderful corners and managed everything with incredible naturalness, making us live the weekend without worries. Super recommended experience, we will definitely be back. Thank you for everything!

Weekend in Ischia and Ventotene: History and Nature

06/10/2026

Michele F.

-

IT

Wonderful holiday! The boat was very comfortable, spacious and always spotlessly clean. A special thanks to Umberto, skipper par excellence: excellent sailor, profound connoisseur of the places visited and always ready to share curiosities and advice. Always available, professional and super nice, he made the experience even more enjoyable. Highly recommended for those who want to experience a relaxing and fun boat holiday with an excellent selection of music!

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

06/10/2026

Antonio D.

-

IT

We stayed on GEM for the weekend in Capri. Hospitality and Top Professionalism! The skipper is a prepared and kind person, the boat is very well maintained and with all the necessary comforts. Experience to be redone, congratulations to Spasso a Vela.

Customer Support

customer support

Do you need support on using the platform or for an online payment? Do you need information or is there something you don't understand? For (almost) any question, we got an answer!

Can't find the perfect holiday for you?

Tell us what you are looking for and let our team find the right solution for you!

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

Let's talk Sailsquare!

HuffpostSailing todayYahoo!

Secure payments

MastercardVisaGoogle PayApple Pay

© 2025 Sailsquare Srl SB • All rights reserved - VAT IT07860990964