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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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5.0

New

Giglio or Elba the pearls of the Tuscan archipelago

Italy: Tuscany

2 days - 2 nights

3 departures available

October - November

€250

Per person

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5.0

EOLIE IN RELAX - Boat with 3 cabins and 3 bathrooms

Italy: Aeolian Islands

6 days - 7 nights

One departure available

October

€607

Per person

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4.9

Relaxing weekend in the Aeolian Islands: Lipari, Vulcano and Salina

Italy: Aeolian Islands

3 days - 2 nights

4 departures available

October

€320

Per person

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4.4

Premium

Cruise to discover Corfu and Ionian Greece - Hostess & Half Board

Greece: Ionian Islands

7 days - 7 nights

One departure available

October

Starting from

€845

€676

Per person - min 2 pax

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4.8

Sunny weekend on Elba from Friday to Sunday

Italy: Tuscany

3 days - 2 nights

One departure available

October

€325

Per person

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5.0

Split archipelago, Hvar islands, Brac - with Hostess and full board

Croatia: Split Archipelago

7 days - 7 nights

One departure available

October

€1,100

Per person

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5.0

Raja Ampat: New Year's Eve in the last paradise

Indian Ocean: Indonesia

12 days - 12 nights

One departure available

December - January

€2,070

Per person

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4.8

Offshore and night navigation course on cabin cruisers

Italy: Tuscany

3 days - 2 nights

One departure available

October

€332

€299

Per person

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New

Gulf of Noli, bay of the Saracens, cave of the Falsari up to Varigotti

Italy: Liguria

1 day - 0 nights

One departure available

September

€99

Per person

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5.0

3 days in the wild Aeolian Islands - All inclusive & flexible dates

Italy: Aeolian Islands

2 days - 2 nights

5 departures available

October - November

Starting from

€723

€650

Per person

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4.7

Sailing cruise in the Greek islands - The Saronic Islands

Greece: Saronic Islands and Athens area

7 days - 7 nights

6 departures available

September - November

Starting from

€700

€665

Per person

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4.7

Tenerife and La Gomera aboard an 18 m ketch

Atlantic islands: Canary Islands

6 days - 7 nights

10 departures available

January - December

Starting from

€900

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

19239 reviews

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

09/29/2026

Mark M.

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GB

We had a brilliant week sailing with Alessandro and Carlo! Alessandro is a very knowledgeable skipper, with brilliant recommendations and excellent choices of destination. Even though our schedule was disrupted by the weather we had a great time sailing round the islands and he provided us with excellent food recommendations each evening. The hospitality on the boat was great, as was Carlo's cooking and I can't recommend the experience enough. Thank you again
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Different flotilla in Ionian Greece: nature, new friends and fun

09/29/2026

Sandro S.

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IT

Even if the holiday had been wonderful I had already decided that I would not have given more than 3/5 for the organizational system of different sailing is among the worst I have seen, and evidently I don't want to make a good impression to have a subsequent discounted holiday The many years of experience of the company of which he boasts, did not make him understand until 3 days before departure that the "rules on boat approvals are more stringent IN GREECE" (as if they had never done it before) having to add an extra boat and divide the crews again by further reducing the groups and redoing the chats of the boats already created with enormous delay. And above all, from this point of view, there was no chat with the whole group of 40 people where everyone could write and get to know each other, but only one for each boat, which from 4 became 5, therefore with fewer people with whom to communicate in a group (they also say they have always done so). The chat can also be used to organize trips IN COMPANY for those who make the same flight/ship/taxi/car and DIVIDE THE EXPENSES. On the contrary, we all arrived as strangers individually, even for those who took the same vehicle and came from the same area. In fact, I made a 20-hour ferry trip discovering at the time of descent that there was another member of the group on the same ship. In addition to the skipper who lives at the expense of the crew (but so I was told that it must be) the co-skipper in the same condition has also been added (fortunately nice), and therefore already at the start there is to add almost what was paid for the boat to have equipment that should already be included, and then to maintain 2 more people. Like all boat holidays you see a price to join but then you have to add almost as much to have a place to sleep, towels, sheets, cleaning, lifesaving tools, etc. Just imagine going to a 5-star hotel and paying extra to have a bed, a bathroom, sheets, towels, cleaning. At the time of booking I called and expressly asked the organizer to avoid the occurrence of situations that punctually happened, as if I had never said anything before, so it was totally useless
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COUS COUS FEST: Un Week End di Mare, Vela, Cous Cous e Musica!

09/29/2026

daria d.

-

IT

It was a very pleasant weekend. Davide managed fun, pleasure and unscheduled events (the rain at sea was still an experience to be lived) while keeping the safety rate high. I was the slouch of the group and I was never made to weigh it down, on the contrary. We went to truly magnificent places. I recommend for beginners and for those who want a relaxing weekend.

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

09/29/2026

Sailor

Excellent experience, clean and efficient boat. excellent, cuisine, top quality food, nice company, owner and staff, they do this job with feeling and dedication, Too bad we didn't get to Hydra., even if it was optional, skipper prepared but a little too plastered in his role. however, experience to be redone with this team, perhaps improving my English and with a new itinerary.

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