Flotilla Vacations – Something for Everyone

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

  • Balance between independent sailing during the day with a friendly social scene in the evening.
  • Mix with up to 12 other yachts, or just go your own way - the choice is yours.
  • A Lead Crew assisting with everything from local knowledge to mechanical support.
  • 18 Flotillas in 5 countries across the Mediterranean and Caribbean, to suit various sailing abilities from Level 1 - 3.


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Flotilla Sailing


Enjoy the perfect balance of freedom and support on a Flotilla vacation with Sunsail. Mix with up to 12 other yachts, or just go your own way – the choice is yours.

What is a Flotilla?

What is a flotilla?

Exploring, socialising and sailing in secret bays and open seas. Guided by expert crews, discovering the world is easy on Flotilla.

Your Lead Crew

What's Included

Find out more about your Flotilla, your Lead Crew and package including fuel, water and optional extras.

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.

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.

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. 


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 26 incredible locations.


Sail the Caribbean this Summer with up to 25% Off

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Book Your 2016 Adventure Early & Save up to 20%

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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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