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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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4.6

Weekend "nel Blu dipinto di Blu" - Ponza & Palmarola

Italy: Pontine Islands

3 days - 2 nights

7 departures available

May - June

Starting from

€230

€207

Per person

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4.7

Easter: Whale watching expedition with WWF guide on an 18-meter schooner

Italy: Pontine Islands

4 days - 3 nights

One departure available

April

€441

€419

Per person

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4.7

1st May: Whale watching expedition with WWF guide on an 18-meter schooner

Italy: Pontine Islands

4 days - 3 nights

One departure available

April - May

€473

€449

Per person

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4.6

Ponte San Pietro e Paolo: adventure to the Pontine Islands!

Italy: Pontine Islands

4 days - 3 nights

One departure available

June

€490

€441

Per person

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4.6

"Nel Blu dipinto di Blu" - midweek in Ponza, Palmarola and Ventotene

Italy: Pontine Islands

4 days - 3 nights

3 departures available

June

Starting from

€320

€288

Per person

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4.6

Ponte San Pietro & Paolo sailing between Ponza, Palmarola & Ventotene

Italy: Pontine Islands

4 days - 3 nights

One departure available

June

€390

€351

Per person

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4.7

2 June: Whale watching expedition with WWF guide on an 18-meter schooner

Italy: Pontine Islands

5 days - 4 nights

One departure available

May - June

€557

€529

Per person

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4.6

Long weekend between Ponza and Palmarola: adventure at the Pontine!

Italy: Pontine Islands

4 days - 3 nights

2 departures available

July

€490

€441

Per person

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From Piombino to Sicily - First stop

Italy: Pontine Islands

7 days - 6 nights

One departure available

May

€1,500

Per person

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4.6

June 2nd long weekend sailing between Ponza, Palmarola & Ventotene

Italy: Pontine Islands

5 days - 4 nights

One departure available

May - June

€350

€315

Per person

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4.6

May 1st long weekend on a sailing boat: adventure to the Pontine Islands

Italy: Pontine Islands

4 days - 3 nights

One departure available

April - May

€430

€387

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

406 reviews

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

10/3/2025

Dean K.

Francesco is an amazing, knowledgeable skipper and makes you feel very welcome. He's open to questions (about anything) and takes time to explain sailing concepts, which is what I needed. We stayed at beautiful, peaceful anchorage and swam in lovely, warm bays. Recommended.
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Life-changing experiences - Escape to the Pontine Islands with photographer on board

09/29/2025

Eve M.

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United Kingdom

Lovely weekend with Francesco who is both knowledgeable and friendly. Thank you for sharing your boat and experience with us! Eve & Dean
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Life-changing experiences - Escape to the Pontine Islands with photographer on board

09/29/2025

Fabrizio G.

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Italy

I couldn't have asked for more: very pleasant company, beautiful and comfortable boat, Francesco very good, nice and attentive. Super recommended, fair winds to everyone!!
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Feast of Santa Candida in Ventotene

09/28/2025

anna maria d.

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Italy

I have Took part in the Ventotene-Festa San Candida tour. Everything was super: the close-knit group, the navigation, the sun and the Sea. I found what I was looking for, lightheartedness and a feeling of freedom. Most of the participants knew each other They, and despite this, have been affectionate and inclusive. Among other things, the skipper was very reliable in bringing us back to port at the requested time, given the train strike. An experience definitely to be redone.

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