Sailing holidays for singles: solo vacations & trips

Sailing holidays for singles: solo vacations & trips

Discover countless experiences for your next sailing adventure. Book your dream holiday starting at €400 a week in 100+ worldwide.


If you find the same experience for a lower price elsewhere, we’ll match the price.

Why sailing holidays are perfect for solo vacations

sailing holiday solo

Embark solo, return with new friends

Bringing together a group of friends for a holiday is a hassle? We have the perfect solution for you! With Sailsquare, share a unique experience at sea with other travellers.

sailing for singles

Discover a new type of holidaying

Venture away from the crowded beaches, and enjoy the full beauty of the sea from the deck of a sailboat or catamaran. Live this magical experience with your crew, explore the treasures of the crystal clear waters by snorkeling and diving, explore islands, toast to the sunset, and go into the night with dancing and laughter.

sailing holidays for singles

Find a holiday that suits your travel tastes

Want a holiday of pure relaxation? Find a holiday with a chef and a hostess aboard a catamaran. Want to experience the thrill of sailing? Find a holiday aboard a racing sailboat in an international regatta. Want to share your experience with lots of new people? Find a flotilla holiday in a beautiful sailing destination.

Why you should book a holiday with Sailsquare?

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The leading sailing holiday marketplace

25,000+ happy travellers, and 10,000+ holidays in 110 destinations worldwide.

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Get onboard solo, with your family, or your friends

Reserve a single spot, a cabin, or a whole boat just for you and your friends or family.

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Discover who’s already onboard

Introduce yourselves online, get to know each other onboard, and go home with a bunch of new friends.

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Sailing holidays that suit all budgets

Rumour has it that sailing holidays are only for the rich or well-connected. With Sailsquare, that's no longer true. Come and discover a world you never thought was accessible!

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