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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

Maddalena Archipelago, southern Corsica: wonderful Sardinia

Italy: Northern Sardinia

6 days - 7 nights

One departure available

September - October

€700

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

Starting from

€585

€527

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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5.0

Super!

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

Greece: Ionian Islands

7 days - 7 nights

4 departures available

October

€570

Per person

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4.8

Super!

Barefoot holiday between Elba and Capraia on a 17m boat - 2 boats in company

Italy: Tuscany

2 days - 2 nights

3 departures available

October

€230

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!

Barcolana 58: a day at the most famous regatta in the world

Italy: Venice and the Gulf of Trieste

1 day - 1 night

One departure available

October

€280

Per person

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4.8

Super!

Aeolian Islands: between sea and authentic flavours

Italy: Aeolian Islands

7 days - 7 nights

2 departures available

September - October

Starting from

€750

€675

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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4.8

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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4.8

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

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

19205 reviews

Sailing course in the Cyclades

09/24/2026

ruggero r.

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IT

Amazing experience!! The skipper followed me step by step, teaching me the basics of sailing with great professionalism and patience. We sailed with a perfect wind to have fun and learn and the nights spent in the roadstead were all in coves of fantastic islets. Highly recommended.

Sporades Experience: Freedom, Turquoise Sea and Greek Magic

09/24/2026

Julie D.

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NL

I had such an amazing week sailing through the Sporades with Gianfranco. From the moment I arrived, I felt very welcome. The boat is absolutely beautiful, very well looked after and always incredibly clean. What I especially appreciated was how much effort Gianfranco puts into making everyone feel comfortable and at home on board. I really enjoyed learning more about sailing from him and getting some actual sailing experience along the way. And then there is the food! Gianfranco is an amazing cook and prepared some of the best lunches and dinners I’ve had in a long time. One of my favourites was a fish risotto with fresh prawns, squid and other freshly caught seafood for lunch. Eating something that fresh and delicious on the boat, surrounded by the beautiful Sporades, was definitely one of the highlights for me. I also feel very lucky with the people I shared this experience with. I came for a sailing trip and left with new friends, new sailing experience and so many beautiful memories. I had a truly wonderful time and will definitely look back on this trip with a big smile. Thank you Gianfranco for making it so special! ⛵️🇬🇷

Feast of Santa Candida in Ventotene

09/24/2026

Alessandra B.

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IT

Nice experience, choreographic and spectacular party, young but very professional skipper, the only negative judgment concerns the boat. I thought the maintenance was poor: exhausted gas cylinder (there was a spare part and it was replaced, but strange not to think about it before boarding), broken light in the cockpit, defective anchor winch, defective stove, defective tender motor, very old and ruined sails.
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Midweek weekend in Elba: sea, scents, colors

09/24/2026

Cecilia M.

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IT

Good morning, I am happy that the sea and wind conditions have allowed us to really go sailing, I have learned that waves and wind are not always in agreement, I have understood how the compass works with degrees, thanks also to the great experience of Ivo who explained everything to us. Elba is so rich that it deserves many more days and means to get closer to the rocks and swim in the caves. On the whole, I would say that I perceived the somewhat austere beauty of sailing in the Tuscan islands. thanks, Cecilia

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