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Whole boat with skipper yacht sailing holidays & tours in Naples & Amalfi Coast

Discover more than 14 opportunities to get on board a Whole boat with skipper adventure in Naples & Amalfi Coast. A unique experience with a local skipper, starting at €350 a week.

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5.0

Positano, Amalfi and Capri by Catamaran

Italy: Naples & Amalfi Coast

7 days - 7 nights

4 departures available

June - July

€1,150

€1,035

Per person

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4.8

Super!

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

April - July

Starting from

€320

Per person

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4.8

Super!

Capri Light Blue - Two boats in company!

Italy: Naples & Amalfi Coast

3 days - 2 nights

10 departures available

May - October

Starting from

€272

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

5 departures available

July - August

Starting from

€900

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

€977

Per person

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4.8

Super!

Capri LightBlue and Positano BluSKy

Italy: Naples & Amalfi Coast

3 days - 2 nights

One departure available

April

€275

Per person

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4.8

All-Inclusive Sailing: Capri, Positano, Amalfi

Italy: Naples & Amalfi Coast

3 days - 2 nights

16 departures available

May - September

€790

€711

Per person

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Capri Light Blue - Two boats in company!

Italy: Naples & Amalfi Coast

3 days - 2 nights

18 departures available

May - October

Starting from

€222

Per person

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4.8

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

Italy: Naples & Amalfi Coast

6 days - 6 nights

3 departures available

June - August

Starting from

€1,150

Per person

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Procida to Ischia: Sailing and Snorkeling Weekend

Italy: Naples & Amalfi Coast

2 days - 1 night

One departure available

May

€380

€342

Per person

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4.8

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

Italy: Naples & Amalfi Coast

5 days - 5 nights

5 departures available

July - September

€1,150

Per person

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4.8

Educational offshore crossing from Salerno to Otranto (or up to Corfu)

Italy: Naples & Amalfi Coast

9 days - 8 nights

One departure available

July

€930

€791

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 - Whole boat with skipper yacht sailing holidays & tours in Naples & Amalfi Coast

142 reviews

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

09/28/2025

Valerie D.

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France

Very nice experience, the boat is comfortable, the whole group was kind. Every day Ilaria made us aware of the life and environment of cetaceans, and their preservation. It was instructive. Rocco is a captain like no other! Very professional, you feel totally safe. Observation, anchoring in the port, swimming... A very good time out of time! Thank you to Rocco, Ilaria, and the other participants for this moment and their kindnesses.
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Long weekend of whale watching with a WWF guide between the Amalfi Coast, Ischia and Capri

09/22/2025

Federica T.

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Italy

Great Captain! Thank you Rocco
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Capri LightBlue and Positano BluSKy

09/16/2025

Claudia D.

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Italy

We have just returned from a beautiful holiday that allowed us to visit wonderful places with a convenient and comfortable boat; Gennaro, was a skipper who was always friendly and attentive to all our needs, he showed great ability and experience even in solving small unforeseen events; definitely to be repeated!!
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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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