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Sailboat yacht sailing holidays & tours in Pontine Islands

Discover more than 28 opportunities to get on board a Sailboat adventure in Pontine Islands. A unique experience with a local skipper, starting at €350 a week.

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4.6

Between the Pontine Islands and the Phlegrean Islands by Sailing Boat

Italy: Pontine Islands

7 days - 7 nights

4 departures available

July - September

Starting from

€719

Per person

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4.8

Super!

ONE WAY From the Phlegraean to the Pontine Islands

Italy: Pontine Islands

8 days - 7 nights

3 departures available

July - September

Starting from

€680

€544

Per person

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4.8

4 days in the Pontine Islands (sailing school)

Italy: Pontine Islands

4 days - 3 nights

3 departures available

July - September

Starting from

€270

Per person

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4.9

Super!

Life-changing experiences - Escape to the Pontine Islands

Italy: Pontine Islands

3 days - 2 nights

6 departures available

July - September

Starting from

€370

€352

Per person

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5.0

Weekend at the Pontine Islands

Italy: Pontine Islands

3 days - 2 nights

8 departures available

August - October

Starting from

€337

Per person

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5.0

Midweek relaxing in the Pontine Mountains

Italy: Pontine Islands

4 days - 3 nights

10 departures available

July - October

Starting from

€337

Per person

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4.9

Super!

Life Changing Experiences - Isole Pontine

Italy: Pontine Islands

3 days - 2 nights

One departure available

August

€430

Per person

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5.0

Pontine Islands aboard a splendid 16-meter sailboat

Italy: Pontine Islands

4 days - 3 nights

4 departures available

July - September

Starting from

€450

Per person

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4.9

Super!

Life-changing experiences: Four days in the Pontine Islands

Italy: Pontine Islands

4 days - 3 nights

5 departures available

July - September

Starting from

€420

€399

Per person

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5.0

Super!

LAST MINUTE Week on a sailing boat among the Pontine COMODI - Only 4 people

Italy: Pontine Islands

6 days - 6 nights

2 departures available

July - August

€950

Per person

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4.9

Super!

Life Changing Experiences - Week in the Pontine Islands

Italy: Pontine Islands

6 days - 6 nights

One departure available

August

€1,100

Per person

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4.9

Week in the Pontine Islands

Italy: Pontine Islands

7 days - 6 nights

2 departures available

August

€690

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 Pontine Islands

1762 reviews

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Life-changing experiences - Escape to the Pontine Islands

07/11/2025

Emanuela P.

First experience on a sailboat, fantastic!!!!!! perfect organization, our skipper Francesco attentive and professional,,made me feel safe at all times.,Thank you for everything
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Sailing weekend in the Pontine Islands

07/10/2025

Stefano M.

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Italy

Beautiful boat trip. I discovered two pearls: lucky those who can reach the Pontine islands habitually. Roberto is a unique skipper. Clearly an expert with many hours of navigation behind him: he knows how to command, manage the boat, put you at ease. Give great tips for living the best on the boat and on land. Excellent cook: he prepares delicious dishes and aperitifs, which make the trip more than pleasant. [hidden] is a super boat!!!! Excellent travel companions met. A real holiday. The head was freed to fully experience all the beauty that was around us. Thank you Roberto.
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Sailing weekend in the Pontine Islands

07/9/2025

Antonio F.

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Italy

We have lived an experience that we will carry in our hearts for a long time. A weekend on a sailing boat that was much more than just an escape from the routine, it was a dive into a dimension made of silence, laughter, salt and freedom. The boat was spacious, clean, cared for in every detail and impeccably organized, you could feel the love and professionalism with which it is managed. The skipper? Extraordinary. Discreet but always attentive presence, he guided us with confidence and passion, making every moment serene and authentic. The organization was impeccable from start to finish, without a hitch, with the constant feeling of being in excellent hands. An experience that we recommend with all our hearts.
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Weekend between Ponza and Palmarola Comfortable - max 4 people

07/8/2025

Claudia S.

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Italy

It was my first experience on a sailboat with an overnight stay and I can't wait to repeat more. David is super helpful and kind. The night at anchor in Palmarola will always remain in my heart. PS: David is also a very good photographer.

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