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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

Sailing adventure in Guna Yala (San Blas Islands) - All inclusive

Caribbean: San Blas Islands - Panama

7 days - 7 nights

6 departures available

January - December

€860

Per person

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5.0

Wellness Adventure Retreat

Caribbean: San Blas Islands - Panama

10 days - 10 nights

6 departures available

February - June

Starting from

€3,000

€2,100

Per person

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4.9

Day at the Gulf of Tigullio on a Sailing Boat - All inclusive!

Italy: Liguria

1 day - 0 nights

9 departures available

June - August

€155

Per person

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4.9

100% female sailing cruises

Greece: Cyclades

7 days - 7 nights

2 departures available

May - October

€990

Per person

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4.4

From Sanremo sailing holiday to discover the Côte d'Azur

France: French Riviera and Porquerolles

4 days - 3 nights

One departure available

December

€380

€342

Per person

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New Year's Eve in the Egadi Islands on a sailing boat - Comfort & All Inclusive

Italy: Aegadian islands

2 days - 2 nights

One departure available

December - January

€510

Per person

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4.8

Long weekend among the wonders of Elba and Capraia

Italy: Tuscany

4 days - 3 nights

12 departures available

June - September

Starting from

€430

€409

Per person

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4.3

Premium

CORSICA SUD Paradise - catamaran cruise with hostess FULL BOARD

France: Corsica

6 days - 7 nights

9 departures available

June - October

Starting from

€1,485

€1,337

Per person - min 2 pax

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Ocean Sailing Initiation in the Canary Islands: 7 days aboard a Pogo

Atlantic islands: Canary Islands

7 days - 7 nights

2 departures available

November - December

€1,200

Per person

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4.1

Conquering the Aeolian Islands - Cook on board

Italy: Aeolian Islands

6 days - 7 nights

18 departures available

May - October

Starting from

€680

Per person

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4.5

Your holiday in the paradisiacal sea of Ibiza & Formentera

Spain: The Balearic Islands

6 days - 6 nights

14 departures available

June - September

Starting from

€790

Per person

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4.4

Easter sailing on the Côte d'Azur

France: French Riviera and Porquerolles

3 days - 3 nights

One departure available

April

€360

€324

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

17617 reviews

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A day sailing in the fantastic Gulf of Trieste

11/11/2025

Armin F.

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Italy

Everything worked out great, Paolo was super helpful!!!! Advice 100%
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Squid Festival: let's close the season on a high note! - on board a 17mt boat

11/10/2025

giulia f.

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Italy

I participated in the weekend on a sailing boat organized for the Squid Festival and I couldn't ask for anything better! It was a wonderful experience, between sea, wind and excellent company. The crew was great: nice people and with a great desire to have fun. The skipper is super professional, but also helpful and attentive to let us experience sailing in a relaxed and fun way. I can't wait to get back on board for the next adventure! ⚓️🐙✨ Giulia, Eva and Martina
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Squid Festival: let's close the season on a high note! - on board a 17mt boat

11/5/2025

Marco F.

-

Switzerland

Matteo is a professional skipper and above all a pleasant person, who steers the boat and situations with lightness and experience. Luke [hidden] a well-maintained and decidedly comfortable and spacious boat. Nice opportunity and fantastic company / crew, not to be forgotten and to be seen again with pleasure in a next navigation, between sea aperitifs and laughter.
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LET'S GO TO TOTANI - Festival in Capria

11/5/2025

Marco D.

-

Italy

Unforgettable and fun experience, very prepared skipper who tamed a sea that was not exactly docile. The fishing competition is beautiful and suggestive.

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