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Sailboat yacht sailing holidays & tours in Naples & Amalfi Coast

Discover more than 13 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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4.7

Midweek sailing trip in the Gulf of Naples

Italy: Naples & Amalfi Coast

3 days - 3 nights

2 departures available

June - July

Starting from

€390

€351

Per person

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4.7

Weekend of sea and colors between Ischia, Procida and Vivara

Italy: Naples & Amalfi Coast

2 days - 2 nights

5 departures available

September - October

Starting from

€275

€234

Per person

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4.8

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

Italy: Naples & Amalfi Coast

7 days - 7 nights

One departure available

August

€977

€879

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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4.8

Super!

7 days between Capri, Amalfi and Sorrento: dream sailing cruise

Italy: Naples & Amalfi Coast

7 days - 7 nights

4 departures available

August

€990

Per person

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4.8

Capri Light Blue - Two boats in company!

Italy: Naples & Amalfi Coast

3 days - 2 nights

4 departures available

June - October

Starting from

€242

€218

Per person

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New

Capri Light Blue - Two boats in company!

Italy: Naples & Amalfi Coast

3 days - 2 nights

10 departures available

June - October

Starting from

€242

Per person

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4.7

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

Italy: Naples & Amalfi Coast

2 days - 2 nights

5 departures available

September - October

Starting from

€320

€272

Per person

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4.8

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

August - September

Starting from

€333

€300

Per person

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4.8

All-Inclusive Sailing: Capri, Positano, Amalfi

Italy: Naples & Amalfi Coast

3 days - 2 nights

11 departures available

June - September

Starting from

€790

€711

Per person

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4.9

Sailing excursion to Capri / Positano

Italy: Naples & Amalfi Coast

1 day - 0 nights

29 departures available

August

€150

Per person

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4.8

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

Italy: Naples & Amalfi Coast

5 days - 5 nights

2 departures available

August - September

€1,150

Per person

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

656 reviews

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June 2nd long weekend between Procida, Ischia and Ventotene

06/6/2026

Valentina G.

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IT

Really nice long weekend of the second of June, well-kept and comfortable boat and group with which we immediately created harmony, also thanks to Umberto, a nice, prepared skipper and a great connoisseur of the places, who organized everything with care, always making us feel at home

June 2nd long weekend: discovering Capri, Ischia and Procida

06/4/2026

Ivana G.

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IT

Very comfortable, spacious and clean sailboat. Gennaro proved to be a nice and helpful skipper, helping to make the experience on board pleasant, and also participating in land trips. Less convincing, however, was the management of the itinerary: the moorings were often far from the coast, even with favorable weather conditions, and the stops did not allow you to explore exclusive places that could only be reached by sea. Furthermore, despite being part of the program, the tender was never used, limiting the possibilities of visiting coves and more hidden areas. Overall, a relaxing and pleasant experience, but below expectations in terms of exploration and itinerary, considering that the context would have allowed it.
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Capri Light Blue - Two boats in company!

06/4/2026

Christian C.

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IT

It's not the first trip I've made with SailSquare, but I can say without hesitation that this was one of the most beautiful experiences I've had so far. Gennaro is an extraordinary skipper and owner: he combines great technical expertise and deep sea experience with a rare ability to put everyone at ease. Always serene, helpful, never tense, always attentive to the safety and harmony of the group. He is one of those people who convey trust from the first moment and with whom it is pleasant to share time, conversations and emotions. Thanks to him we spent unforgettable days, sailing in total safety but above all in an atmosphere of authentic conviviality. On her boat you feel like guests, not customers: it is cared for in every detail, welcoming, full of comfort and attention that make you feel how much it is loved and lived by those who drive it. I take home wonderful views, new friendships and memories that will last a long time. A heartfelt thank you to Gennaro for the passion, culture, humanity and elegance with which he accompanied us in this experience. I really hope to be back on board his boat soon.
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In the blue of Capri and the infinity of the Amalfi Coast

05/30/2026

Alessandra C.

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IT

Beautiful experience, very pleasant crew. Gennaro really made a difference both for his experience but also for his kindness! Highly recommended!!

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