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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

Super!

Capri LightBlue and Positano BluSKy

Italy: Naples & Amalfi Coast

3 days - 2 nights

3 departures available

October

Starting from

€294

Per person

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4.8

Super!

3 days - Sorrento, Capri, Positano, Amalfi - Luxury Sailing Yacht

Italy: Naples & Amalfi Coast

3 days - 2 nights

10 departures available

September - October

Starting from

€1,325

Per person

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4.8

Super!

Capri and Amalfi Coast by catamaran - ALL INCLUSIVE

Italy: Naples & Amalfi Coast

3 days - 2 nights

2 departures available

September - October

Starting from

€1,800

Per person

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4.7

Long weekend of whale watching with a WWF guide between the Amalfi Coast, Ischia and Capri

Italy: Naples & Amalfi Coast

3 days - 3 nights

One departure available

September

€452

Per person

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4.7

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

Italy: Naples & Amalfi Coast

2 days - 2 nights

One departure available

October

€275

€248

Per person

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4.9

Catamaran cruise to discover Amalfi, Capri, Positano, Ischia

Italy: Naples & Amalfi Coast

7 days - 7 nights

One departure available

October

€1,480

€1,332

Per person

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4.3

Premium

Capri Dream Premium - Catamaran cruise full board

Italy: Naples & Amalfi Coast

6 days - 7 nights

One departure available

October

Starting from

€1,260

Per person - min 2 pax

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A terrace overlooking the sea: a day to discover the Gulf of Naples

Italy: Naples & Amalfi Coast

1 day - 0 nights

39 departures available

September - October

Starting from

€110

€88

Per person

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4.8

All Inclusive: Procida, Capri, Positano, Amalfi, Cetara, Sorrento

Italy: Naples & Amalfi Coast

6 days - 6 nights

One departure available

September

€1,385

Per person

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4.7

Weekend of sea and colors between Ischia, Procida and Vivara

Italy: Naples & Amalfi Coast

2 days - 2 nights

One departure available

September

€275

€248

Per person

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5.0

Capri, Sorrento, Positano and Amalfi by Catamaran

Italy: Naples & Amalfi Coast

5 days - 4 nights

2 departures available

September

Starting from

€650

€585

Per person

Why book a holiday with Sailsquare?

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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

689 reviews

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Capri LightBlue and Positano BluSKy

09/14/2025

Maurizio G.

-

Italy

Everything went well prepared skipper helpful and nice beautiful Capri beautiful
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La Flottiglia Mediterranea: Capri, Ischia, Procida e le isole Pontine

09/11/2025

Federico L.

-

Italy

Really a great experience, due to the weather we had to change the plans a bit but overall everything went well!
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La Flottiglia Mediterranea: Capri, Ischia, Procida e le isole Pontine

09/10/2025

Francesco S.

-

Italy

It was not a simple holiday. It was a symphony of wind and sea, thanks to "La Flottiglia" which turned my first sailing holiday into a fantastic experience. Almost every night we spent in the middle of the blue, far from the ports and close to the essence of freedom. Sleeping under the stacks of Capri was something unique: the calm sea, the stars above us and the silence that makes you really feel part of that landscape. We visited wonderful islands: Capri, Ischia, Procida, Ventotene, Ponza and Palmarola. Each one has given us something different, including colors, landscapes and unforgettable moments. The evening at the Terraces in Ponza was one of the funniest! The catamaran parties were super fun, and getting to know the people from the other boats made it even more interesting. Each with its own story, its own spirit, and a great desire to have fun. If I could, I would go back tomorrow. In fact, I wouldn't have gotten off the boat at all!
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Capri LightBlue and Positano BluSKy

09/10/2025

DANIELE R.

-

Italy

Beautiful weekend with a very pleasant crew... Precise skipper and perfect boat: clean, comfortable and spacious... Gennaro is a very prepared, helpful and nice skipper!! He guided us in a punctual and clear way and made us become familiar with the activities of the boat!! He was able to create a good atmosphere right from the start!! The "breakfast at dawn with a view of the Faraglioni of Capri" is a moment that is "priceless"... Really a good experience, thank you all until next time!!

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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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