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Sailboat holidays & skippered tours

The thrill of sailing, the chance to discover places only accessible by sea and to meet new friends are what make a sailing holiday magical. Treat yourself to a week or weekend where you can wake up in the roadstead and have breakfast with the sea around you.

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4.8

Super!

Premium

Sailing paradise in Greece on a big 50 ft boat: the best local experience

Greece: Saronic Islands and Athens area

6 days - 7 nights

7 departures available

August - October

Starting from

€1,300

€780

Per person

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4.7

In the blue of Capri and the infinity of the Amalfi Coast

Italy: Naples & Amalfi Coast

2 days - 2 nights

4 departures available

October

Starting from

€275

Per person

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4.7

Maddalena Archipelago, southern Corsica: wonderful Sardinia

Italy: Northern Sardinia

6 days - 7 nights

3 departures available

September - October

Starting from

€700

Per person

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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!

Learn to sail in Liguria: First level sailing course

Italy: Liguria

2 days - 1 night

One departure available

October

€220

Per person

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5.0

Super!

Crystal clear sea, relaxation, skipper and hostess on board! What more could you want?

Greece: Ionian Islands

7 days - 7 nights

4 departures available

September - October

Starting from

€570

Per person

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5.0

Super!

Pack your suitcase and we'll take care of the rest!! Stewards on board!

Greece: Ionian Islands

7 days - 7 nights

5 departures available

September - October

Starting from

€570

Per person

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4.7

Long weekend of whale watching with WWF guide on an 18-meter schooner

Italy: Tuscany

3 days - 3 nights

2 departures available

September

Starting from

€452

€429

Per person

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4.8

Super!

Cast off for a week at sea, a thousand ways to experience it!

Greece: Saronic Islands and Athens area

7 days - 7 nights

5 departures available

September - November

Starting from

€585

€527

Per person

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4.8

Super!

Aeolian Islands: between sea and authentic flavours

Italy: Aeolian Islands

7 days - 7 nights

5 departures available

September - October

Starting from

€750

€675

Per person

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4.9

Super!

Gulf of Poets

Italy: Liguria

3 days - 2 nights

One departure available

September

€280

Per person

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5.0

We have known the Aeolian Islands for 20 years, live them with us!

Italy: Aeolian Islands

7 days - 7 nights

3 departures available

September - October

€690

Per person

Why book a holiday with Sailsquare?

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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

Book a single spot, a cabin or the whole boat just for yourself, or for your friends or family.

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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 holidays & skippered tours

18837 reviews

Unforgettable adventure in the Aeolian Islands

08/25/2026

Cristina D.

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IT

Extremely bad experience – boat and owner management absolutely to be avoided Our experience on this boat during the holiday in the Aeolian Islands from 15 to 22 August 2026 was extremely negative and, based on what we have experienced, I do not recommend either this boat or the owner's management. Unforeseen events during a boating holiday can certainly happen. The problem, however, is how they are managed. In our case we encountered a series of technical, maintenance and organizational problems that significantly compromised the quality of the holiday. We suffered a serious failure in the electrical system: a problem with the alternator caused damage to a battery, leaving us without electricity for a period and, subsequently, with an extremely limited availability of energy. The consequences were heavy: refrigerator not working, difficulty or impossibility of using the bathrooms and related electrical drains, shower, lighting, phone charging, windlass and other on-board utilities. The situation was not resolved with a simple intervention: in the following days several mechanics intervened, at different times, in an attempt to restore the operation of the boat. It was also necessary to resort to a power station to be able to keep some essential services active. We also had problems with the photovoltaic system, initially believing that the latter were due to battery failure. Subsequently, however, the technicians who intervened on board found cables and connections of the photovoltaic system seriously deteriorated and burned. As far as we were told during the interventions, their state appeared to be attributable to a pre-existing deterioration and not simply to the failure that occurred during the holiday. This has contributed to making it very difficult to maintain the boat's energy autonomy. Added to this was the change of skipper communicated only two days before departure. The new skipper spoke only English and created considerable communication difficulties within the group, especially during maneuvers and when we had to manage breakdowns and communicate with the mechanics on board. Among the aspects that affected us negatively was also the equipment of the kitchen: upon our arrival we found cutlery and utensils completely rusty and not suitable for use. The problem was not solved during our stay: only at the end of the holiday, after our specific report, the owner proceeded to replace the utensils and cutlery. In fact, the replacement took place when our holiday was over. Finding rusty utensils intended for the use of guests raises serious doubts about the attention paid to checking the condition of the boat and its equipment between bookings. I am talking about problems that, as a whole, have concretely affected livability, hygiene, functionality and the quality of the experience. What left me most disappointed was the behavior of the owner. Faced with the numerous problems that emerged, I had the clear impression several times that his main objective was to minimize his responsibilities and find a justification for the problems, rather than listening to the guests and trying to minimize the inconvenience. Unforeseen events can happen but As far as I am concerned, this experience has left a deep disappointment. I would not choose this boat again and I would not recommend it to other Sailsquare users. My considerations are based exclusively on personal experience during the holiday and are supported by photographs and documentation of the interventions carried out on board.

SAIL & ENJOY: in the blue painted blue of the Aeolian Islands

08/25/2026

Luca Vincenzo Carlo A.

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IT

The week on the boat was pleasant thanks to a wonderful crew with whom a good bond was immediately created and who guaranteed a great mood for the duration of the holiday. The boat is very nice and spacious, and the staff is efficient in keeping it clean, taking care of the guests by cooking great dishes and also selecting very nice shore trips. Respectable bonus for the sound system. The Aeolian Islands, ça va sans dire, are a destination with a strong appeal and have kept expectations very high. However, there is a huge "but" hanging over my judgment. I think it is not acceptable that a destination like Stromboli can be arbitrarily sacrificed by the itinerary without a real reason, even if adding the wonderful Alicudi, depriving us of the spectacle that makes the Aeolian Islands unique when both the week before and the week after the itinerary has included this destination. The boat, despite being presented as a single boat, sails together with three others and, if on the one hand this allows for beautiful moments of sharing and friendship, on the other hand it affects the itinerary. As well specified, it is obvious that the last word belongs to the skipper on the route but I would have appreciated more dialogue with the crew and greater transparency with respect to the choices regarding it. Ultimately, the boat parties are beautiful, the food and music are excellent, but for some if not for many, these are secondary aspects when you decide to visit magical places like the Aeolian Islands, I would take them into consideration more for the future. It could have been a perfect holiday, it will still be a nice holiday.
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Sailing in the magical Sardinia of the South

08/25/2026

Sara S.

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BE

We visited beautiful places, hidden bays and sailed with [hidden], a well-maintained and very performing boat. We were able to make long sails also thanks to the presence of a nice sailor who supported the skipper, Unfortunately, however, the sailings were not always pleasant due to the very irascible and sometimes excessively competitive attitude of the skipper. There was good harmony between the crew, unfortunately, however, the very despotic management of the skipper created several tensions, especially with regard to food: it was not possible to collaborate in the preparation of meals, manage the galley (purchased from us) or propose culinary alternatives, and some special personal dietary needs (in my case not to eat red meat or in the case of others, intolerances) were often experienced as a complication, triggering angry scenes of the skipper and creating situations of great discomfort. Overall, the places visited, the boat and the crew were very positive aspects. Too bad that the skipper's attitude and excessively rigid management ended up conditioning the experience, preventing it from being fully lived with the serenity, pleasure and spirit of collaboration that it deserved.

SLOW SAIL - sailing from San Vincenzo to Capraia and Corsica

08/25/2026

eris n.

-

IT

All wonderfully fantastic

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