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. 

Special Interest Flotillas

Wine & Culinary Flotillas

Wine & Culinary Flotilla

Combine the thrills of a Flotilla sailing adventure with mouth-watering insights into the culinary cultures of Croatia or Italy.

Exclusively Adults Flotilla

exclusively adults flotilla

Enjoy a Flotilla with other like-minded sailors on our Exclusively Adults Flotillas setting sail next summer from Lefkas. 

Belize Whale-Shark Flotilla

Belize Whale-Shark Flotilla

Dive with the gentle giants of the ocean in Belize on this incredible Flotilla departing April 21 - 30, 2016. 

Learn how to sail on a Flotilla

Flotilla Hero to Zero Holidays

Flotilla zero to hero

Earn your ICC or RYA Start Yachting  and enjoy an amazing Flotilla experience in Greece or Croatia.


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.


Find out what specials we are offering this week

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Why should you sail with Sunsail for your vacation?

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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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