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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

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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4.4

Guadalupe to St. Martin via Antigua, Barbuda, St. Barth, and Anguilla

Caribbean: Saint Martin

14 days - 14 nights

One departure available

February

€1,490

€1,341

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

4 departures available

October - November

€723

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

5 departures available

October - November

€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

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5.0

New

Basic and advanced sailing courses

Italy: Liguria

2 days - 1 night

3 departures available

October - November

Starting from

€220

€198

Per person

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New

Weekend in the Pontine Islands

Italy: Pontine Islands

3 days - 2 nights

2 departures available

May

€450

Per person

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4.7

From Funchal to Lanzarote: adventure and unforgettable emotions

Atlantic islands: Canary Islands

6 days - 7 nights

One departure available

December

Starting from

€900

Per person

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4.3

The perfect holiday on Europe's hottest and most glamorous island

Malta: Malta

6 days - 6 nights

One departure available

October

€690

Per person

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4.7

Tuscany and Liguria, we sail between the Apuan Alps and the Gulf of Poets

Italy: Liguria

2 days - 2 nights

3 departures available

April - October

Starting from

€250

Per person

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4.1

Corso di vela RYA Day Skipper Pratical sailing

Italy: Tuscany

4 days - 4 nights

11 departures available

October - December

€1,400

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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