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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!

Come and discover Guadeloupe and its archipelago: a paradise on the water

Caribbean: Guadeloupe

7 days - 7 nights

9 departures available

January - December

€850

Per person

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4.8

Super!

Let's discover the Aeolian Islands together by sailing

Italy: Aeolian Islands

7 days - 7 nights

25 departures available

May - October

Starting from

€600

Per person

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4.8

Super!

Come and discover Guadeloupe and its archipelago: a paradise on the water

Caribbean: Guadeloupe

6 days - 6 nights

4 departures available

February - December

€730

Per person

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5.0

Super!

We have known the Aeolian Islands for 20 years, live them with us!

Italy: Aeolian Islands

7 days - 7 nights

18 departures available

May - October

Starting from

€689

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

€337

Per person

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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

21 departures available

May - October

Starting from

€1,000

€950

Per person

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5.0

Super!

Weekend at the Pontine Islands

Italy: Pontine Islands

3 days - 2 nights

One departure available

October

€337

Per person

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4.9

Super!

Sailing cruise in the Greek islands - The Saronic Islands

Greece: Saronic Islands and Athens area

7 days - 7 nights

26 departures available

March - September

Starting from

€650

€618

Per person

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4.9

Super!

Cyclades and Microcyclades with a magnificent 15-meter boat

Greece: Cyclades

7 days - 7 nights

3 departures available

May - June

Starting from

€750

Per person

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4.8

Super!

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

Italy: Northern Sardinia

6 days - 7 nights

14 departures available

June - September

Starting from

€625

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 - November

Starting from

€460

Per person

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5.0

Super!

We have known the Aeolian Islands for 20 years. - Live them with us.

Italy: Aeolian Islands

7 days - 7 nights

2 departures available

October - November

€583

Per person

Why book a holiday with Sailsquare?

The world's largest marketplace for sailing holidays

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

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 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

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

17589 reviews

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Barcolana weekend in Trieste and surroundings.

10/15/2025

Barbara M.

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Italy

MARINO fantastic skipper, he pampered us ( swim in the blue included), he was very helpful for all our whims. The Barcolana is a grandiose spectacle, seen from the sea it excites a lot, if you like sailing you can not avoid being there at least once. The kitten on board, Lightning is a very sweet travel companion. After the restyling in the shipyard, the catamaran will also be up to the task.
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Weekend in Capraia, the island with timeless sunsets

10/14/2025

Gloria G.

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Italy

Wonderful weekend. Super skipper! Very professional and helpful, he entertained us by telling us many curiosities about sailing and the places visited. The fantastic boat with ample space and equipped with everything you need! 100% recommended both the skipper and the destination!
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European Offshore Mile Builder - Leg 5: St Tropez to Malta

10/14/2025

David J.

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France

Very skilled captain and good ambiance crew However: -state /cleanliness of the boat nok for me, really not maintained enough -no wind=> no sail, nearly only motoring: maybe better to find another formula to allow for more saling? or clearly indicate that it is possible that there is no sailing
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Barcolana 2025: experience the most beautiful regatta with me!

10/14/2025

Gabriele I.

-

Italy

Very good Gianni

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