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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

5 departures available

September - October

Starting from

€363

€290

Per person

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4.8

Super!

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

Italy: Naples & Amalfi Coast

7 days - 7 nights

One departure available

August

€999

€899

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

18 departures available

August - 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

3 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

2 departures available

September

Starting from

€452

€429

Per person

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4.8

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

Italy: Naples & Amalfi Coast

5 days - 5 nights

One departure available

August

€1,115

Per person

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5.0

Capri, Sorrento, Positano and Amalfi by Catamaran

Italy: Naples & Amalfi Coast

5 days - 4 nights

4 departures available

September

Starting from

€650

€585

Per person

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4.3

Premium

Capri Dream Premium - Catamaran cruise full board

Italy: Naples & Amalfi Coast

6 days - 7 nights

3 departures available

August - October

Starting from

€1,260

Per person - min 2 pax

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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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4.6

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

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

639 reviews

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

08/15/2025

Marco F.

-

Switzerland

Top week, absolutely to be done again! The boat was very beautiful and well maintained, with an excellent sound system that accompanied many moments of relaxation and fun. Gennaro, our skipper, was professional and always attentive to safety, managing to combine organization and rather flexible hours for breakfast, lunch and evening disembarkation. The locations visited were splendid and the company on board proved to be close-knit and collaborative, especially in the preparation of meals, creating a convivial and pleasant atmosphere. The only note: a little more sailing would have made everything perfect... But the magic of this week will remain etched in the memories for a long time!
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From the Pontine to the Amalfi Coast by sailboat

08/14/2025

Federico G.

-

Italy

Just finished (unfortunately) a beautiful one-week holiday on a sailing boat on the Pontine islands. On board we found Leonardo, a super professional skipper, young but with a lot of experience, never a line out of place and always available to fulfill any request and with 10 people on board it is not easy! The boat is also beautiful, super positive experience, we will definitely see you again next year, thank you for everything Leo! 😉👍🏼💪🏼
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An unforgettable week between Capri, Positano, Amalfi, Ischia, Procida...

08/12/2025

Alessandro C.

-

Italy

I have had several experiences similar to this but I must say that Gennaro particularly impressed me for how he puts his guests at ease and above all in safety. He is particularly good at involving the crew in giving navigation information, really involving everyone in the maneuvers and always in total safety. If you are thinking of taking a sailing holiday and you are at your first experience, La Gennaro boat could be your best choice.
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An unforgettable week between Capri, Positano, Amalfi, Ischia, Procida...

08/12/2025

Giampaolo T.

-

Italy

Gennaro fantastic skipper... Super professional always attentive to the safety and care of his guests. The boat is equipped with every comfort to allow the crew to spend fantastic days on board. The places visited and the new adventure friends made the holiday unforgettable!

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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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