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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

3 departures available

October

€1,300

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

2 departures available

October - November

€585

Per person

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4.9

Super!

The fantastic Saronic Islands and the surroundings of Athens

Greece: Saronic Islands and Athens area

7 days - 7 nights

2 departures available

October

€750

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

3 departures available

October

€570

Per person

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4.8

Super!

Squid Festival on the Island of Capraia - 2 boats in company (22 seats)!

Italy: Tuscany

3 days - 2 nights

One departure available

October

€280

Per person

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4.7

Voices of the Pelagos: artistic-scientific whale watching expedition with WWF guide

Italy: Tuscany

4 days - 4 nights

One departure available

October

Starting from

€453

Per person

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4.9

Super!

Adventure weekend in the Egadi Islands

Italy: Aegadian islands

3 days - 2 nights

5 departures available

October - November

€350

Per person

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4.8

Super!

Squid Festival on the Island of Capraia - 2 boats in company (22 seats)!

Italy: Tuscany

3 days - 2 nights

One departure available

October

€280

Per person

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5.0

Super!

Barcolana Weekend: experience the largest regatta in the world

Italy: Venice and the Gulf of Trieste

3 days - 2 nights

One departure available

October

€420

Per person

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4.8

Super!

Experience the sea in October!

Italy: Tuscany

2 days - 2 nights

4 departures available

October

€200

Per person

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4.9

Super!

Two days in Elba without worries with a professional skipper

Italy: Tuscany

2 days - 2 nights

One departure available

October

€315

Per person

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5.0

Super!

Midweek relaxing in the Pontine Islands

Italy: Pontine Islands

4 days - 3 nights

2 departures available

October

€370

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.

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

On Sailsquare, sailing holidays are within everyone's reach. Thousands of proposals to choose from, at affordable prices.

Reviews - Sailboat holidays & skippered tours

19240 reviews

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AMERICA'S CUP in pursuit of the AC40s!

09/29/2026

Marzia B.

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IT

A wonderful day Everything perfect and well organized Highly recommend

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.

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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.

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