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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

Super!

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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4.7

Amazing Pontine Islands on a sailboat with private bathrooms

Italy: Pontine Islands

3 days - 2 nights

2 departures available

September

Starting from

€312

Per person

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4.8

Super!

Come and discover the Saronic Islands from Poros

Greece: Saronic Islands and Athens area

6 days - 6 nights

3 departures available

September

€600

Per person

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5.0

Super!

Weekend at the Pontine Islands

Italy: Pontine Islands

3 days - 2 nights

6 departures available

September - October

Starting from

€370

Per person

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4.8

Super!

All in the family: 5 days between Elba and Capraia on a 17m boat - 2 boats in company

Italy: Tuscany

5 days - 4 nights

3 departures available

September

€490

€466

Per person

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4.8

Super!

A week of sailing and sea life on the island of Elba

Italy: Tuscany

7 days - 7 nights

3 departures available

September - October

€650

Per person

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4.9

Super!

NEW YEAR's Eve between sea and land in Norway: chasing the Northern Lights - COTTAGE + SAILBOAT

North Sea: Norway

11 days - 11 nights

One departure available

December - January

€1,300

Per person

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5.0

Super!

Mykonos and the Western Cyclades by sail, with skipper and on-board kitchen

Greece: Cyclades

6 days - 6 nights

2 departures available

September

Starting from

€1,000

€750

Per person

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4.9

Super!

Sail to the edge of the world among the wonders of the North (cottage + sailboat)

North Sea: Norway

7 days - 7 nights

One departure available

October

€1,200

Per person

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5.0

Super!

Pula - Monfalcone

Croatia: Istrian peninsula

6 days - 6 nights

One departure available

August - September

€950

Per person

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4.8

Super!

From Tavolara to Ogliastra, the great emotions of Eastern Sardinia

Italy: Southern Sardinia

5 days - 4 nights

One departure available

September

€1,200

Per person

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4.8

Sailing in the magical Sardinia of the South

Italy: Southern Sardinia

6 days - 7 nights

2 departures available

August - September

€790

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

18916 reviews

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Different flotilla in Ionian Greece: nature, new friends and fun

08/29/2026

Lucian Alexandru L.

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IT

A memorable experience.
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Flotilla Different: Party and new friends in the Aeolian Islands - SAILOR CABIN ONLY

08/29/2026

Alberto Z.

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IT

Beautiful experience, excellent organization, thanks go to Simone for his commitment and dedication, as well as to the staff, the skippers and with praise for our Pablito, good both at sea and in the console. A holiday not so suitable for those seeking relaxation 😎
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Sailing to discover the Egadi Islands

08/29/2026

Francesca B.

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IT

Fantastic week, ema and Irene are experienced, competent, kind and super nice. They welcome you as if you were at home. They know the sea and sudden changes and this made me feel very safe: how can a storm come if the sky is completely starry and the sea is a table?!? And instead, just as they had predicted, it was better not to leave😅 ready to advise alternatives and support in activities if you cannot navigate, kind mediators in the dynamics of unknown people. Their route, outside the classic Egadi tour, allowed us to see dolphins, turtles, the coast of Scopello, the zingaro reserve and San Vito. With the "good" wind on the way back we also did a wonderful 3-hour🥰🥰🥰 sail Thank you thank you Ema and Ire... fair winds and I hope our routes will re-meet soon ❤️❤️❤️❤️

A sailing holiday: discovering the Pontine Islands

08/29/2026

PAOLO S.

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IT

Marco is a capable and responsible skipper. I would have liked to go ashore a few more times to visit the islands.

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