Flotilla sailing holidays

Your group. Your route. Discover together.

Explore some of the world’s best cruising grounds with the support and reassurance of a Sunsail lead crew on a flotilla holiday.

Flotilla holidays offer an informal, relaxed and unique experience for families, couples and groups across 4 stunning sailing grounds in the British Virgin Islands, Greece, and Croatia.

If you’d rather someone takes the helm for you, you can hire a skipper for the duration of your holiday. We also offer the chance to learn to sail whilst on flotilla, with Flotilla Starter and Flotilla Hero course in Greece and Croatia.

Keep an eye out for our special flotillas too, with our food and wine flotillas available in Croatia and Italy, and an Adults Only Flotilla in Croatia.  

Whether you are unqualified, a new skipper or an old hand, there’s a flotilla for you. Great for solo sailors, groups, couples and families, flotillas are the way to go for social sailing.

NEW! Sail By The Cabin 

Travelling solo or as a couple, and don’t need the whole yacht? Our Sail By The Cabin holidays let you book your own cabin on one of our yachts complete with a skipper. Enjoy a sailing holiday as part of a flotilla on three dates in September and October in Croatia and Greece. Find out more

Flotilla destinations

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
Ithaca, Greece

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

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

British Virgin Islands

  • Visit a real-life Treasure Island
  • Steady trade winds, calm currents
  • World-famous yachting destinations
Flotillas Experience level 1
Explore British Virgin Islands

Specialist flotillas

Food and wine 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.

Book a Croatia Food and Wine flotilla, including vineyards tours and wine tastings for just £100 more per boat than our standard flotilla price!

Dubrovnik food and wine flotilla

Dubrovnik, Croatia

2019 departure date: 2 June 2019

Wine and sail

Agana food and wine flotilla

Marina Agana, Croatia

2019 departure dates: 8 June, 7 & 14 September 2019

SailEATalia Sail, Wine & Taste of Italy flotilla

Procida, Italy

2019 departure dates:  4 May, 18 May, 25 May, 1 June, 29 June, 13 July, 27July, 28 September, and 12 October.

SailEATalia Sail, Wine & Taste of Italy flotilla in Sicily

Portorosa, Italy

Departure dates in 2019: 15 June & 14 September

Exclusively for adults flotilla

Hvar one-week flotilla

Marina Agana, Croatia

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 for adults flotilla departs on 22 June 2019 same route as a Hvar one week flotilla.

How does a flotilla 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 included
  • 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.

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44 yrs
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