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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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4.8

All Inclusive Tour: Capri, Amalfi, Cetara, e Sorrento

Italy: Naples & Amalfi Coast

5 days - 5 nights

2 departures available

August - September

€1,150

Per person

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4.7

Amazing Capri and Amalfi Coast on a sailboat

Italy: Naples & Amalfi Coast

4 days - 3 nights

One departure available

July - August

Starting from

€458

Per person

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5.0

Capri, Sorrento, Positano and Amalfi by Catamaran

Italy: Naples & Amalfi Coast

5 days - 4 nights

One departure available

September

€645

€581

Per person

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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

712 reviews

Weekend of sea and colors between Ischia, Procida and Vivara

06/19/2026

FEDERICA L.

Really great sailing weekend! In addition to the beauty of the experience and the places visited, I had the opportunity to learn many things about the world of sailing. A special thanks to Emiliano, who with great competence and passion explained the operation of the boat, actively involving us and letting us try out different activities on board. It was a beautiful way to experience the sea not only as a passenger. Experience that I absolutely recommend to those who want to combine fun, adventure and learning!
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Weekend of sea and colors between Ischia, Procida and Vivara

06/17/2026

Domenico T.

This was my first boat adventure and what an adventure, starting from the boat which is much more spacious than I expected, passing to Emiliano, the skipper, who with his professionalism and sympathy explained the rudiments of navigation and finally the location, Ischia and Procida, which are a spectacle of Campania.

Weekend of sea and colors between Ischia, Procida and Vivara

06/17/2026

Domenico R.

Beautiful sailing experience between Naples, Ischia and Procida. Emiliano is a kind and helpful skipper who manages to make the experience special, actively involving those who want to feel part of the crew. Highly recommended!

Weekend of sea and colors between Ischia, Procida and Vivara

06/17/2026

Sabrina C.

I left for a weekend with "Spasso a vela" and it was an unforgettable experience. The boat is very comfortable, equipped with all possible amenities, it is very spacious, the cabins are comfortable and the 3 bathrooms on board are more than enough to feel comfortable. During our weekend we encountered slightly rough seas and a bit of wind but despite this thanks to the skipper's navigation experience, both in managing the navigation and in finding strategic points to dock, the weather conditions that were not entirely favorable did not weigh on us at all, so we fully enjoyed the beautiful landscapes and the sea. It was also super interesting to participate actively in life on board, the skipper taught us a lot of notions and involved us in the maneuvers. It is an experience that I recommend and that I will definitely return to do with "Spasso a vela".

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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

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