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

Greece: Saronic Islands and Athens area

6 days - 7 nights

2 departures available

October

€1,300

Per person

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4.8

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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

One departure available

October

€750

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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5.0

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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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5.0

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

Greece: Ionian Islands

7 days - 7 nights

2 departures available

October

€570

Per person

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5.0

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Midweek relaxing in the Pontine Islands

Italy: Pontine Islands

4 days - 3 nights

One departure available

October

€370

Per person

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5.0

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Daily sailing trips to Ortigia and Plemmirio

Italy: Sicily

1 day - 0 nights

27 departures available

October - November

€150

Per person

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5.0

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Croisière de rêve sous voiles dans les îles de la société 14 Jours

Pacific Ocean: French Polynesia

13 days - 13 nights

One departure available

October - November

€2,090

Per person

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4.8

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A taste of the magnificent Island of Elba

Italy: Tuscany

2 days - 2 nights

5 departures available

October - November

€300

Per person

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4.9

Super!

Sailing adventure in Norway: chasing the Northern Lights - COTTAGE + SAILBOAT

North Sea: Norway

7 days - 7 nights

6 departures available

January - November

€1,200

Per person

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4.8

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Barefoot holiday between Elba and Capraia on a 15m boat - 2 boats in company

Italy: Tuscany

2 days - 2 nights

2 departures available

October

€230

Per person

Why book a holiday with Sailsquare?

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

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

19263 reviews

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

10/6/2026

Iris D.

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BE

Such a wonderful experience! As a solo traveller I had a great time during this trip, Aga and Arnon were very welcoming and took good care of us. The places we visited were stunning, the food Aga prepared for us was excellent, and the overall vibes were 10/10.
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Experience the sea in October!

10/6/2026

Luigi V.

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IT

Super experienced and helpful skipper. He helped us learn the basics of sailing and life on a sailing boat. Great chef skills!
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Dreamy Saronics: turquoise waters and relaxation just a stone's throw from Athens

10/6/2026

Marcos B.

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US

Alessio was a great host/skipper and I had an amazing week with him and my other "boatmate" passenger, Victoria. The boat is stunning and I booked a cabin to myself which had its own private bathroom. If you're traveling alone, that's the way to go. Weather didn't cooperate much but I was there for the experience on the boat which was exactly what I got. Alessio is very skilled in handling the boat.... and a great cook! All in all, can't recommend Alessio and his boat, [hidden] enough. Grazie mile, Alessio :)

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

10/6/2026

Thomas S.

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DE

Andrea & Caroline let us experience a very nice holiday week. Andrea as skipper, who not only has excellent local knowledge of the islands, beaches and local conditions, but also always made sure that it was safe and comfortable on board for us as inexperienced sailors. Caroline's role as a fairy godmother on the boat ensured that the physical well-being was never neglected, culinarily the dishes, breakfast and lunch were simply first-class beyond any expectation. She not only made sure that you felt very comfortable, but also showed very quickly with many little things that she pays a lot of attention to her guests, their preferences and wishes. This was a very pleasant, relaxed week, which I can only recommend, so also my fellow travelers have expressed. After a very short time, you have the feeling that you are not just a guest, but rather a good friend who is visiting. I can only highly recommend it, with Andrea & Caroline we were in competent, courteous & hospitable hands. Thank you very much for that and best regards to Crete.

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