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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

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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

23 departures available

May - October

Starting from

€1,200

€1,080

Per person

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4.8

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Sardinia and Corsica on a 17-metre sailboat with 4 cabins and 4 bathrooms

Italy: Northern Sardinia

6 days - 7 nights

17 departures available

June - October

Starting from

€660

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

One departure available

October - November

€585

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

33 departures available

March - October

Starting from

€460

Per person

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4.9

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Cruise-Coastal Navigation Course Porquerolles-Calanque Cassis

France: French Riviera and Porquerolles

6 days - 7 nights

8 departures available

July - August

Starting from

€800

Per person

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4.9

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SLOW SAIL - sailing from San Vincenzo to Capraia and Corsica

France: Corsica

7 days - 6 nights

4 departures available

August

Starting from

€750

Per person

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4.8

Super!

Sea, wind, sailing, fun and relaxation Tuscan Archipelago and Corsica

Italy: Tuscany

6 days - 6 nights

13 departures available

June - September

Starting from

€990

Per person

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4.9

Super!

Lefkas, Kefalonia & Ithaca: 7 days of relaxation and fantastic bays

Greece: Ionian Islands

7 days - 7 nights

10 departures available

May - July

Starting from

€650

€585

Per person

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5.0

Super!

Daily sailing trips to Ortigia and Plemmirio

Italy: Sicily

1 day - 0 nights

16 departures available

October - November

€150

Per person

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5.0

Super!

Dream Cruise Under Sail in the Society Islands 14 Days

Pacific Ocean: French Polynesia

13 days - 13 nights

One departure available

October - November

€2,090

Per person

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4.8

Super!

A taste of the magnificent Island of Elba

Italy: Tuscany

2 days - 2 nights

4 departures available

October - November

€300

Per person

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4.9

Super!

Squid Festival in Capraia

Italy: Tuscany

3 days - 3 nights

One departure available

October - November

€280

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

19280 reviews

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

10/18/2026

Laura P.

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IT

The Barcolana is an indescribable regatta, Antonio is an excellent captain attentive and precise, the crew a nice discovery, we can't wait to do it ❤️ again
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Sailing in the Cyclades

10/18/2026

Tanya S.

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GR

I had a very special week with Yann sailing around the cyclades ... He is very kind , funny amazing person to be with, while being super professional , organized and knowledgeable of every little stone , port , path , view , mountain, restaurant , cafe , bar in the Cyclades !! I really thank Yann for such a beautiful holiday :)))
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IBIZA and FORMENTERA - ALL INCLUSIVE with skipper and skipper

10/17/2026

Elena V.

We really needed this holiday! Filippo is a wonderful host: attentive skipper (also ready to involve those who show interest in sailing), excellent cook, great entertainer and even singer. The weather was not the best, which changed the itinerary and it was a great shame, but it is the risk of every holiday, even more so in those by boat. The latter is equipped with interesting "pluses" (BBQ, fishing rods, SUP). It is comfortable, but it is "lived" practically all year round as it is basically Filippo's home and this means that it is not a 5-star hotel on the water where everything is impeccable. A thread of sporting spirit and sharing is needed, as clearly written in the announcement. Finally, I cannot fail to mention Nao, a wonderful sailing companion always ready to be cuddled and try to save you when you go down into the water. And if I loved it because I don't have any particular liking for dogs, you can trust it. Ps: you will go home with a couple of extra kilos on you, but it's worth it

Learn to sail in Liguria: First level sailing course

10/17/2026

Nicole C.

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IT

Unforgettable experience on the legendary [hidden]. Even before getting on board, Orazio, with great professionalism, deepened the previous experiences of his crew with whom he shared choices and organization. Once on board, we were greeted by wonderful people and we were amazed by the beauty of the boat, perfectly tidy, clean and welcoming. It is said that when you are at sea all your thoughts remain on land and so it was, between many laughs and exquisite company, we also learned new notions of sailing and life at sea in general. Super recommended experience. Nicole and Matteo from Aosta.

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