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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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4.8

Super!

From the Pontine to the Amalfi Coast by sailboat

Italy: Naples & Amalfi Coast

8 days - 7 nights

One departure available

August - September

€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!

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

24 departures available

July - October

Starting from

€1,325

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

7 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

10 departures available

August - 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

14 departures available

July - October

Starting from

€795

Per person

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5.0

The coasts along Amalfi - (18-40 years old)

Italy: Naples & Amalfi Coast

7 days - 7 nights

13 departures available

July - October

Starting from

€795

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

577 reviews

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From the Pontine to the Amalfi Coast by sailboat

07/14/2025

Anna P.

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Switzerland

Overall nice experience: beautiful places visited, good Skipper Leonardo, nice crew. Since this is the first time on this route, we have paid for the inefficiency of the organization in providing the right contacts in the various stages of navigation. In addition, there were problems with the tender that did not allow the whole crew to move freely in the various coves.
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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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