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

Discover more than 15 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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4.8

Super!

From the Pontine to the Amalfi Coast by sailboat

Italy: Naples & Amalfi Coast

8 days - 7 nights

4 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!

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!

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!

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

10 departures available

July

€300

Per person

Why book a holiday with Sailsquare?

The world's largest marketplace for sailing holidays

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

82 reviews

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Capri LightBlue and Positano BluSKy

07/8/2025

Marianna D.

Vacanza SUPER!!! Skipper bravissimo e molto competente! Compagni di viaggio MERAVIGLIOSI! Posti da 10elode!! Da Ripetere
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Capri LightBlue and Positano BluSKy

07/8/2025

Kaled E.

-

Italy

Mi familia y yo hemos vivido una experiencia de ensueño en un velero fantástico. Capri, Positano, Bagni della Regina, Li Galli, sitios estupendos, aguas de un azul indescriptible. Gennaro como skiper demuestra una competencia más allá de cualquier duda, metódico, lógico, didáctico (siempre ofrece una explicación del porqué y de como hacerlo), siempre gentil, sereno y atento de cualquiera de nuestras dudas o de lo que necesitáramos. Una navegación impecable y segura. Nuestros compañeros de viaje, como si nos conocieramos de una vida. Altamente recomendada, por supuesto que repetiremos.
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Capri LightBlue and Positano BluSKy

07/7/2025

Francesco L.

-

Italy

Esperienza meravigliosa, skipper impeccabile nella sua disponibilità, compagnia super. Assolutamente da ripetere
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All Inclusive Tour: Capri, Amalfi, Cetara, and Sorrento

07/6/2025

Sasa G.

-

Slovenia

We were a group of five women and Alessandro took us to all the beautiful places we had hoped to see. From the start, we felt completely safe and well looked after. He was kind, discreet, and attentive, always making sure we were comfortable and enjoying ourselves. Thanks to Alessandro, we experienced some truly magical moments and places.

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