Sailing holidays for couples with a skipper
A sailing holiday offers the perfect opportunity of a break for two - whether that means a weekend, or something longer. Get onboard with your loved one and sail into the sunset, relax on remote beaches, discover uninhabited islands, and experience the magic of sailing together!
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If you find the same experience for a lower price elsewhere, we’ll match the price.
Sailing holidays for couples: the ultimate adventure!
Enjoy quality time together
A sailing holiday with your loved one one is the perfect way to switch off for the day to day stresses and spend time together. Sailing trips offers more undisturbed moments than you might think. Explore uninhabited islands, swim in empty coves, explore private beaches, and enjoy the sunset with a glass of red wine on the deck of the yacht.
Experience unforgettable moments and breathtaking scenery
A sailing trip through Sailsquare is sure to bring unforgettable moments that you can share for years to come with your partner. Watch dolphins or whales, snorkel with sea turtles, and enjoy local delicacies at charming harbor dinners.
Share your experience with others couples if you like!
Do you enjoy spending time together, but also enjoy socialising with others? Then we have just the experiences for you! You have the opportunity to enjoy undisturbed moments as a couple, but you also have communal time to get to know your crew during dinners or on excursions ashore.
The best sailing destinations and holidays for your next couple adventure
Sailing holidays in Northern Sardinia with a local skipper
Sailing holidays in Tuscany with a local skipper
Catamaran sailing holidays with a skipper
Sailing holidays in Italy with a local skipper
Crewed sailing holidays with a skipper
Sailing holidays in Greece with a local skipper
Sailing holidays in the Pontine Islands with skipper
Why you should book a holiday with Sailsquare?
The leading sailing holiday marketplace
25,000+ happy travellers, and 10,000+ holidays in 110 destinations worldwide.
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.
Discover who’s already onboard
Introduce yourselves online, get to know each other onboard, and go home with a bunch of new friends.
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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