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Sailboat yacht sailing holidays & tours in Naples & Amalfi Coast

Discover more than 14 opportunities to get on board a Sailboat 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

€660

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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4.7

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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Procida to Ischia: Sailing and Snorkeling Weekend

Italy: Naples & Amalfi Coast

2 days - 1 night

10 departures available

July

€300

Per person

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4.8

Two hearts and a sailboat: discovering the Phlegrean Islands

Italy: Naples & Amalfi Coast

2 days - 2 nights

12 departures available

July - October

Starting from

€312

Per person

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5.0

The coasts along Amalfi - (40+ years)

Italy: Naples & Amalfi Coast

7 days - 7 nights

15 departures available

July - October

Starting from

€795

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 - Sailboat yacht sailing holidays & tours in Naples & Amalfi Coast

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

07/8/2025

Laura D.

-

Italy

È stata un'esperienza molto piacevole, siamo stati fortunati perché il gruppo ha funzionato bene da subito. Le destinazioni non necessitano di commenti: sono posti incantevoli! Lo skipper Gennaro ci ha accuditi e ci ha fatti sentire rilassati e al sicuro. Esperienza consigliata per vivere il mare nel suo pieno senso e in tutta la sua bellezza
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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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In the blue of Capri and the infinity of the Amalfi Coast

07/7/2025

Claudia D.

-

Italy

Tutto super!

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