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Whole boat with skipper yacht sailing holidays & tours in Pontine Islands

Discover more than 11 opportunities to get on board a Whole boat with skipper adventure in Pontine Islands. A unique experience with a local skipper, starting at €350 a week.

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4.9

4 days in the Pontine Islands (sailing school)

Italy: Pontine Islands

4 days - 3 nights

One departure available

September

€270

Per person

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4.9

Super!

Life Changing Experiences - Week in the Pontine Islands with photographer on board

Italy: Pontine Islands

6 days - 6 nights

One departure available

August

€1,100

Per person

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4.9

Super!

Life-changing experiences: Four days in the Pontine Islands with photographer on board

Italy: Pontine Islands

4 days - 3 nights

3 departures available

September

Starting from

€420

€399

Per person

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4.6

ONE WAY From the Phlegraean to the Pontine Islands

Italy: Pontine Islands

7 days - 7 nights

2 departures available

August - September

Starting from

€660

Per person

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4.8

Super!

A sailing trip through history, food and wine of the Pontine Islands

Italy: Pontine Islands

7 days - 7 nights

One departure available

August

€950

Per person

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4.6

Feast of Santa Candida in Ventotene

Italy: Pontine Islands

3 days - 3 nights

One departure available

September

€395

Per person

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4.9

Super!

Life-changing experiences - Escape to the Pontine Islands with photographer on board

Italy: Pontine Islands

3 days - 2 nights

3 departures available

September

Starting from

€370

€352

Per person

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5.0

4 days between Ponza and Palmarola in relaxation

Italy: Pontine Islands

3 days - 3 nights

One departure available

August

€500

Per person

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5.0

Pontine Islands aboard a splendid 16-meter sailboat

Italy: Pontine Islands

4 days - 3 nights

2 departures available

September

Starting from

€450

Per person

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5.0

Weekend at the Pontine aboard a splendid 16-meter sailboat

Italy: Pontine Islands

3 days - 2 nights

3 departures available

September

Starting from

€420

Per person

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4.9

Weekend in the Pontine Islands (sailing school)

Italy: Pontine Islands

3 days - 2 nights

One departure available

September

€300

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 - Whole boat with skipper yacht sailing holidays & tours in Pontine Islands

330 reviews

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Between the Pontine Islands and the Phlegrean Islands by Sailing Boat

08/17/2025

Antonio S.

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Italy

A beautiful experience between the islands with the skipper Gennaro who was much more than just a companion, managing to make this week magical, relaxing and tasty with his dishes. Spacious and comfortable boat, diverse and breathtaking itinerary. A unique experience that I already think back on with so much nostalgia. Until next time!
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Pontine Blue - Midweek Escape

08/16/2025

Erica P.

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Italy

Wonderful experience, beautiful places, special people, terrific skipper! Highly recommended!
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Between the Pontine Islands and the Phlegrean Islands by Sailing Boat

08/12/2025

Rossella C.

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Italy

Beautiful holiday with extraordinary people (which a boat is not always taken for granted!). The boat was comfortable and well organized (The thing I really appreciated were the cushions at the bow to comfortably sunbathe!) ❤️ A mix of relaxation and fun in beautiful places and a lot of sailing thanks to the wind and the sea that "hijacked" our holiday. Thanks to Luca our skipper who turned out to be a really nice person. Discreet, nice, professional and very prepared, he managed to put us at ease immediately. We decided together, under his advice, to change course and this gave us a lot of unexpected surprises!! Thank you Luca! Now I know what I'm going to do next year!!! Let's try the Pontine again! See you soon! Fair winds! ⛵️
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Pontine Blue - Midweek Escape

08/12/2025

Emanuele S.

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Italy

What can I say really wonderful experience. My partner and I already knew the Pontine islands, but discovering them and experiencing them on a sailboat was a wonderful surprise. This is mainly thanks to Skipper Lele who, with his experience and ability, takes you to explore unique corners of paradise (and thanks to his intuition we were most of the first to arrive and fully experience the unspoiled beauty). This experience also allows you to experience the boat at 360 degrees feeling of participation and not just guest. Aperitifs, lunches and dinners and long chats during navigation will remain imprinted. I would have been hours listening to our skipper's stories about the sea. Last and not least, the attention to the safety of Lele, who was always vigilant and prudent and never lowered his attention. I recommend this experience to everyone because once you get off the boat you will take with you small life lessons that will be useful in everyday life. Thanks again Lele from Sara and Emanuele!

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