Flotilla Vacations – Something for Everyone

Time to yourself, time to be with friends and always the time of your life.

  • 23 Flotillas including 7 new holiday options in the Mediterranean and the Caribbean
  • Flotillas to suit all tastes and sailing abilities Level 0 - 3
  • Beach BBQ's, Adventure, End of the Flotilla Regatta


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Flotilla Sailing


Enjoy the feeling of freedom and the safety of support every day on a Flotilla with Sunsail. Mix with up to 12 other yachts, or just go your own way…

Caribbean flotilla sailing holidays


Choose 1 or 2 weeks’ line-of-sight sailing in the British Virgin Islands or try the two week Level 3 Flotilla from our new St. Lucia base.

North American flotilla sailing holidays

Greece - Mediterranean

Explore the Ionian, the Cyclades, Sporades or the Saronic Gulf on a choice of 1 and 2 week Flotillas.

Croatian flotilla sailing holidays

Croatia - Mediterranean

Dubrovnik or Dalmatian Islands? Choose from 5 Flotilla routes, designed to give you the best of this destination whichever you choose. 

Turkish flotilla sailing holidays

Turkey - Mediterranean

Spice it up a bit on one of our Turkish Flotillas and immerse yourself in a cultural sailing experience, from Gocek or Turgutreis.

Your Lead Crew

Your Lead Crew

Skipper, Hostess and Engineer come with enthusiasm and experience. Kids’ Activities Coordinator during school vacations.

North American sailing holidays

the social scene

Great for making new friends, Sunsail creates chances to mingle with like-minded fellow Flotilla sailors after a day on the water. 


Our fleet of yachts

The best value, the biggest choice and the latest yachts and catamarans from 35–53ft.



New to Sailing?

Even if you’ve never set foot on board a boat before, you can enjoy a sailing vacation in your choice of 27 incredible locations.


Enjoy 10% off on Advanced Charter Bookings

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Last Minute Offer on Select Sailing Vacations

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Brochure Request

Our Sunsail Vacations, Schools and Events brochures, will help give you that extra inspiration. Request your copy and start planning your next adventure!

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