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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!

From the Pontine to the Amalfi Coast by sailboat

Italy: Naples & Amalfi Coast

8 days - 7 nights

2 departures available

July - September

Starting from

€680

€598

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

2 departures available

August

€950

Per person

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4.8

Super!

Capri LightBlue and Positano BluSKy

Italy: Naples & Amalfi Coast

3 days - 2 nights

4 departures available

September - October

Starting from

€294

Per person

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4.8

Super!

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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4.8

Super!

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

Italy: Naples & Amalfi Coast

7 days - 7 nights

3 departures available

August

€999

Per person

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4.8

Super!

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

Italy: Naples & Amalfi Coast

6 days - 6 nights

3 departures available

July - September

Starting from

€1,385

€1,316

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

25 departures available

July - 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

5 departures available

July - October

Starting from

€1,800

Per person

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4.7

Whale watching cruise with WWF guide between the Amalfi Coast, Ischia and Capri

Italy: Naples & Amalfi Coast

5 days - 6 nights

One departure available

July

€1,009

€959

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

€452

€429

Per person

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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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Procida to Ischia: Sailing and Snorkeling Weekend

Italy: Naples & Amalfi Coast

2 days - 1 night

9 departures available

July

€300

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

619 reviews

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Short sailing cruise in the Gulf of Naples

07/11/2025

Daniela D.

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Italy

My first experience on a sailing boat was an unforgettable experience, when the Universe puts the right people on your path at the right time. Every moment was intense, perfect and unforgettable, despite the rough sea, the change of tour due to the wind and the sea was all organized and managed calmly and with great professionalism and safety by Alessandro who was our skipper. Thank you for these three unforgettable days where we shared beautiful moments and the magic of being perfect strangers but immediately all old friends. A sensation never experienced. A gift like the breeze, the sun, the sea and the sense of touching freedom and embracing it totally.
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Capri LightBlue and Positano BluSKy

07/8/2025

Marianna D.

SUPER holiday!! Very good and very competent skipper! WONDERFUL travel companions! Places from 10elode!! To be repeated
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In the blue of Capri and the infinity of the Amalfi Coast

07/8/2025

Laura D.

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Italy

It was a very pleasant experience, we were lucky because the group worked well right away. The destinations do not need comment: they are enchanting places! The skipper Gennaro looked after us and made us feel relaxed and safe. Recommended experience to experience the sea in its full sense and in all its beauty
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Capri LightBlue and Positano BluSKy

07/8/2025

Kaled E.

-

Italy

My family and I have had a dream experience on a fantastic sailboat. Capri, Positano, Bagni della Regina, Li Galli, wonderful sites, waters of an indescribable blue. Gennaro as a skiper demonstrates a competence beyond any doubt, methodical, logical, didactic (he always offers an explanation of why and how to do it), always gentle, serene and attentive to any of our doubts or what we need. Impeccable and safe navigation. Our fellow travelers, as if we had known each other for a lifetime. Highly recommended, of course we will repeat.

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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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