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

Discover more than 12 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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4.7

Feast of Santa Candida in Ventotene

Italy: Pontine Islands

3 days - 3 nights

One departure available

September

€420

Per person

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5.0

Super!

Long Weekend Santa Candida - Ventotene

Italy: Pontine Islands

5 days - 4 nights

One departure available

September

€550

Per person

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5.0

Super!

Weekend of the Pontine Islands to discover Ponza and Palmarola

Italy: Pontine Islands

3 days - 2 nights

2 departures available

September

€490

€441

Per person

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5.0

Weekend in the Pontine Islands

Italy: Pontine Islands

3 days - 2 nights

One departure available

September

€295

Per person

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4.9

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

Italy: Pontine Islands

6 days - 6 nights

One departure available

August - September

€1,100

Per person

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4.8

Weekend of emotions in the Blu Pontino

Italy: Pontine Islands

3 days - 2 nights

One departure available

November

€225

Per person

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4.3

Week on a 22m maxi-yacht between Pontine and Flegree

Italy: Pontine Islands

7 days - 6 nights

One departure available

August - September

€1,390

Per person

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New

Weekend in the Pontine Islands

Italy: Pontine Islands

3 days - 2 nights

2 departures available

September

Starting from

€367

Per person

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4.8

Pontine Blue - Midweek Escape

Italy: Pontine Islands

4 days - 3 nights

One departure available

November

€225

Per person

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4.9

4 days in the Pontine Islands

Italy: Pontine Islands

4 days - 3 nights

One departure available

September

€420

Per person

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4.7

From the Aeolian Islands to the Pontine Islands - Adventure, Navigation, and Relaxation - One Way

Italy: Pontine Islands

6 days - 6 nights

One departure available

September

€590

€531

Per person

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5.0

Santa Candida between Ventotene and Palmarola

Italy: Pontine Islands

4 days - 3 nights

One departure available

September

€390

Per person

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

557 reviews

The Mediterranean Flotilla: Capri, Ischia, Procida and the Pontine Islands - ONLY MEN SEATS

08/26/2026

Anna M.

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IT

The experience overall was positive as a good atmosphere was created on board among the participants. However, there were several aspects that did not satisfy me and for which I do not think I will book another trip with Sailsquare, much less with the organizer LAFLOTTIGLIA.IT. First of all, I was looking for a flotilla experience, which for what was my knowledge of the term, meant a sailing cruise with a significant number of boats. My expectation was 5-6 boats, not 3. I had chosen this package because I had already had an experience with 3 boats and I was looking for something more aggregating, with greater participation. This aspect unfortunately combined with the fact that, despite some offer from the skipper to join another boat, most of the time they spent their time alone. We have also heard rumors from other participants of a misalignment between skippers that may have influenced the aggregation. Another negative aspect concerns the fact that the organizer LAFLOTTIGLIA.IT created the Whatsapp group, then disappeared. I tried to contact him by phone and via whatsapp and, despite the constant views of group chats, he did not consider it necessary to respond to one of his customers. The first night on the boat was traumatic for all the participants as it was impossible to fall asleep due to the very high presence of mosquitoes, due to the lack of disinfestation of a river near the Marina of Castellammare di Stabia. For weather reasons, we spent the first night in this marina and, since the last night in the marina (Friday evening) was scheduled in the program, we decided (all the participants of the 3 boats without exception) to find an alternative accommodation for that last night which, I repeat, was scheduled to be spent on the boat. I personally asked the organizer LAFLOTTIGLIA.IT and Sailsquare to recognize us a contribution for the night in the hotel that we paid for as we believed that the conditions offered by the organization, well aware of the situation in the marina, were not acceptable and that it was not correct to postpone the matter to a "simple presence of mosquitoes foreseeable on a sailing trip", This response, received by Sailsquare and not by the organizer as it was not reachable, was not considered acceptable as the incident was anything but ordinary. It also seemed to us a very unsmart choice, commercially speaking, reputationally, not to meet us as the conditions of the marina were certainly known to the organizer, therefore, if the organizer consciously chooses to have his passengers/travelers face this discomfort (I'm not talking about the first night but the last one that was scheduled in the program), something makes me think that he had a convenience starting from that marina. As for our skipper, I have no particular comments to make, he was a helpful and friendly person even if there were some communication problems during the holiday, specifically when we were talking about the itinerary to follow or the options available for the day / evening, which were always resolved peacefully although with tones sometimes a little too "heated" for my standards.
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A week with friends in the Pontine Mountains - embarkation from Procida

08/26/2026

Martina M.

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IT

A truly unforgettable week on the boat! Much of the credit goes to our skipper Umberto who immediately managed to put us at ease with his sympathy, availability and professionalism. He was much more than just a skipper: always present, attentive to our needs and able to create a special atmosphere on board, making us feel immediately at home. A special mention also goes to his skills as a chef! He delighted us with really delicious dishes, prepared with care and passion. Thanks to him we experienced a week of sea, relaxation, laughter, good food and many moments that we will take with us. An exceptional skipper, a special person and... Not a bad chef! If we were to leave tomorrow, we would have no doubts about who to choose!
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Between the Pontine Islands and the Phlegraean Islands by Sailing Boat

08/25/2026

Antonia C.

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IT

It was a great experience and our skipper Luca was amazing! A very prepared person, full of initiatives and above all a participant in the group.

Between the Pontine Islands and the Phlegraean Islands by Sailing Boat

08/24/2026

Raffaella C.

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IT

With various sailing experiences, I must say that the skipper Luca, despite being young, which scared me a bit at first, knows how to handle the boat in an excellent way, like a real sea dog. A very polite and nice person with all the crew. Very well maintained boat. So everything went above expectations.

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