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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!

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

Italy: Naples & Amalfi Coast

6 days - 6 nights

2 departures available

July - August

Starting from

€1,150

Per person

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4.8

Super!

7 days between Capri, Amalfi and Sorrento: dream sailing cruise

Italy: Naples & Amalfi Coast

7 days - 7 nights

4 departures available

August

€990

Per person

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4.8

An unforgettable week between Capri, Positano, Amalfi, Ischia, Procida...

Italy: Naples & Amalfi Coast

7 days - 7 nights

One departure available

August

€977

€879

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

5 departures available

September - October

Starting from

€275

Per person

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4.6

Capri, Ischia and Amalfi Coast by catamaran with hostess and cook

Italy: Naples & Amalfi Coast

7 days - 7 nights

2 departures available

August

Starting from

€1,990

€1,791

Per person

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4.8

Super!

All-Inclusive Sailing: Capri, Positano, Amalfi

Italy: Naples & Amalfi Coast

3 days - 2 nights

7 departures available

July - September

€790

Per person

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4.8

Super!

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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4.8

The gems of the Amalfi Coast: Capri Light Blue, Positano Blue Sky, Amalfi Dreaming History

Italy: Naples & Amalfi Coast

4 days - 3 nights

2 departures available

August - September

Starting from

€333

Per person

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4.4

Premium

CAPRI Paradise - Catamaran cruise with hostess FULL BOARD

Italy: Naples & Amalfi Coast

6 days - 7 nights

9 departures available

July - October

Starting from

€1,320

€1,188

Per person - min 2 pax

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4.8

Capri Light Blue - Two boats in company!

Italy: Naples & Amalfi Coast

3 days - 2 nights

2 departures available

September - October

€242

€218

Per person

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4.9

Sailing excursion to Capri / Positano

Italy: Naples & Amalfi Coast

1 day - 0 nights

21 departures available

August

€150

Per person

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Procida to Ischia: Sailing and Snorkeling Weekend

Italy: Naples & Amalfi Coast

2 days - 1 night

5 departures available

July - August

Starting from

€280

Per person

Why book a holiday with Sailsquare?

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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.

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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

690 reviews

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

07/7/2026

Giuseppe I.

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GB

It was a fantastic weekend: super comfortable boat and skipper always attentive to the needs of the group, which allowed us to live a wonderful experience,
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Capri Light Blue - Two boats in company!

07/5/2026

Roberta P.

-

IT

Very nice destination, prepared skipper, homogeneous company all of the same age, very comfortable boat

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

07/5/2026

Francesca R.

-

IT

Beautiful experience, enchanting places, extraordinary landscapes that fill the eyes and heart, excellent lunches. Very prepared skipper and always attentive to any need... thanks for ❤️
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Midweek sailing trip in the Gulf of Naples

07/4/2026

Andrea Z.

-

IT

The skipper gennaro is a pleasant and helpful person, unfortunately the weather was not on our side, boat well maintained and tidy. Positive Opinion

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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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