Flotilla sailing holidays

Your group. Your route. You discover together.

Join a sociable group of fellow sailors to explore some of the world’s best cruising grounds on a flotilla holiday, with the support of a Sunsail lead crew. Choose from a range of high performance yachts sailing spectacular destinations by day and socialising with new friends in fantastic restaurants and bars by night.

Flotilla holidays are perfect for families and groups looking to make friends and share new experiences. Learn to sail or improve your skills, or even hire a skipper to take the pressure off. Sail the beautiful British Virgin Islands or discover ancient Greece, sample Croatia’s finest cuisine or discover Turkey’s Turquoise Coast on a flotilla sailing holiday.

Keep an eye out for our special flotillas, which we change every year. This year we’re looking forward to our Belize whale shark flotilla, exclusively adults flotilla,Sunsail 36 One Design flotillaCroatian culinary and wine flotilla and our Amalfi coast culinary and wine flotilla.

View our Flotilla brochure here.

Flotilla destinations

7 nights from £1,505

Athens, Greece

  • Ancient relics and ruins
  • Exciting blue water sailing
  • Catch the famous Meltemi wind
Flotillas Experience level 3 ICC RYA
Explore Athens, Greece
7 nights from £1,054

Lefkas, Greece

  • Easy, rewarding sailing
  • Sail the famous Heptanese Islands
  • Enjoy fantastic watersports
Flotillas Experience level 1-2 ICC RYA Sailing school
Explore Lefkas, Greece
7 nights from £1,844 Dubrovnik_Croatia

Dubrovnik, Croatia

  • Gentle winds and occasional Mistrals
  • Rich history and spectacular scenery
  • Line-of-sight navigation and island hops
Flotillas Experience level 2 ICC RYA
Explore Dubrovnik, Croatia
7 nights from £1,782 Hvar Town, Hvar Island

Marina Agana, Croatia

  • Easy line-of-sight sailing
  • Short island hops and longer trips
  • Explore quiet islands and national parks
Flotillas Experience level 1-2 ICC RYA Sailing school
Explore Marina Agana, Croatia
7 nights from £1,866

Göcek, Turkey

  • Calm conditions and consistent winds
  • Explore the renowned Turquoise Coast
  • Dive, snorkel and kayak the Aegean Sea
Flotillas Experience level 1-2 ICC RYA
Explore Göcek, Turkey
7 nights from £1,483 British Virgin Islands

Tortola, BVI

  • Visit a real-life Treasure Island
  • Steady trade winds, calm currents
  • World-famous yachting destinations
Flotillas Experience level 1 Sailing school
Explore Tortola, BVI

Special interest flotillas

Wine and culinary flotillas

If exploring the world of local wines and traditional culinary treats is your passion these flotillas are perfect for you. They combine some of the best sailing in the Mediterranean with tastings of local produce and the chance to meet the artisans who make it.


Amalfi Coast culinary and wine flotilla

Procida, Italy

Dates departing: 9 July, 8 October (SOLD OUT) and 15 October 2016

Wine and sail 

Croatian culinary and wine flotilla

Agana, Croatia

Dates departing: 4 June 2016, 11 June 2016, 10 September 2016, 17 September 2016, 24 September 2016

Whale shark flotillas

On our special whale shark flotilla you'll arrive during the annual migration of these magnificent animals, sailing out to Belize's best dive sites to encounter the world's largest fish in its natural habitat.

10-day whale shark flotilla


This flotilla will run on one date only, departing 21 May 2016. Due to popular demand, this flotilla is sold out.

Week whale shark flotilla


This flotilla will run on one date only, departing 21 April 2016. 

Watch this space for new dates for 2017 or alternatively sign up to our newsletter to be the first to hear when we go on sale.

Additional special interest flotillas

Mljet one design flotilla

Dubrovnik, Croatia

Join us for a one-off flotilla comprised exclusively of Sunsail 36i’s, combining the thrill of optional day races with plenty of time to discover the incredible Dubrovnik sailing area.

This flotilla is for one date only, departing 8 May 2016.

Exclusively adults flotilla

Lefkas, Greece

Families love our flotilla holidays, but what about groups of adults and couples looking for all the benefits of a flotilla, in a child-free environment?

Our exclusively adult Kalamos flotilla route departs 3 July 2016.

How does it work?

A common misperception of the flotilla is that you have to sail like ‘ducks in a row’. But sailing on a flotilla offers much more independence than that.

Every day your lead crew will brief you on your destination, weather updates and any must-see spots along the way. They’ll help you cast off in the morning and then sail direct to the next destination so they can be there to help everyone moor up at night.

But after that, you’ll be left to explore the high seas yourself. Whether you’re looking for some exciting sailing or searching for the perfect beach, you can sail with confidence knowing that any assistance from your lead crew is only a phone or radio call away.

You’ll mostly stay in village quays and small harbours, and every night you can choose to explore on your own or meet up with the rest of your flotilla for dinner and stories.

The lead crew also organise social events like barbecues on the beach, punch parties and an end of week regatta so you can get to know your flotilla sailing partners.

What's included?

We’ve created a flotilla package just for you, so all you have to worry about is choosing which of our incredible routes to go for and when.

What's incuded
  • Fully equipped cruising yacht for the duration of your holiday

  • Lead Crew: Skipper, Host and Technician
  • One tank of yacht fuel*
  • Full cylinder of cooking gas and full tank of water
  • Guaranteed mooring at each stopover
  • Dinghy and outboard
  • All sailing, navigation and safety equipment onboard
  • Fully equipped galley/kitchen
  • All clean linen including bath and tea towels
  • Snorkelling Equipment
  • First Morning Breakfast
  • Flotilla Punch Party
  • End Cleaning
  • End of Week Regatta

*Fuel is not included on our specialist flotillas in Italy 

What's not included

Lead crew support

The lead crew is there to support you. They'll help you cast off each day before heading to that evening's stopover to help you moor when you arrive. You can be as independent as you like with the confidence that the lead crew will be there to lend a helping hand when you need it. They can also recommend the best anchorages, harbours, restaurants and places to visit, ensuring that you make the most of your time on holiday.

Onboard your lead boat will be a skipper, host and a technician. On dedicated family flotillas in Greece we add an activities coordinator to help entertain the kids.


Your flotilla skipper is fully RYA qualified and is responsible for the flotilla. They will be on hand at the beginning and end of every day if you need assistance with mooring or casting off. They also hold daily chart briefings to help you make the most of your trip.


Your flotilla host will know the best beaches, restaurants and local attractions. They’ll find the perfect place for dinner every evening for you and your flotilla, so you can enjoy delicious local cuisine while sharing tales of the sea with your new friends.


Your technician will be on hand to make sure that each yacht in the flotilla is running smoothly. Should you have any technical questions, just let your technician know and they’ll be there to help.

Activities coordinator

Available on certain flotillas during the school holidays, our activities coordinator is on hand to give you some time to yourself without having to worry about what the kids are up to. They provide fun beach games and activities to keep kids from five to 17 years old entertained.

Digital brochure

Download our 2016 brochure today.

Waterlines eMagazine

Inspiring stories, insightful reviews, helpful hints and tips.

Sign up for our newsletter!

Keep up-to-date and receive £100 off your next holiday.

Choose Sunsail

Destinations worldwide
Flotilla routes
Types of yachts
40 yrs
Creating holidays
4 hr
Service guarantee
ABTA – The Travel Association
Consumer protection