Flotilla 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 stunning sailing grounds in the British Virgin Islands, Greece, and Croatia.

If you can’t sail or would 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 in Croatia and Italy.  

So plan early and get ahead of the curve for your pick of the fleet in the British Virgin Islands, GreeceItaly, and Croatia.

Whether you are unqualified, a new skipper or an old hand, there is a flotilla for you. Great for groups, couples and families with children, social sailing is the way to go.


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
  • Discover Croatia's rich and two-millennia old history
Flotillas Experience level 1 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 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 1 ICC RYA
Explore Dubrovnik, Croatia
Procida, Italy

Procida, Italy

  • Perfect for experienced sailors
  • Gateway to the famous Amalfi Coast
  • Luxurious resorts, bustling towns, quiet villages
Flotillas Experience level 2 ICC RYA
Explore Procida, Italy
Aeolian Islands

Portorosa, Italy

  • Relaxed sailing with consistent winds and volcanic islands
  • Clear, warm waters ideal for snorkelling
  • Spectacular black sand beaches
  • Europe’s second largest active volcano
  • UNESCO-protected Aeolian Islands.
Flotillas Experience level 2 ICC RYA
Explore Portorosa, Italy

Sardinia, Italy

  • Excellent food and wine
  • Glamorous resorts and quiet anchorages
  • Dynamic sailing off famous Costa Smerelda
Flotillas Experience level 2 ICC RYA
Explore Sardinia, Italy

Special interest 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 vineyard tours and wine tastings for just a little more per boat than our standard flotilla price!

Wine and sail

Agana food and wine flotilla

Marina Agana, Croatia

2020 departure dates: 6 June and 12 September 

SailEATalia Sail, Wine & Taste of Italy flotilla in Procida

Procida, Italy

2020 Departure Dates:  May 2, May 16, May 23, May 30, June 27, July 4, July 11, July 25,  September 26October 3 and October 10


SailEATalia Sail, Wine & Taste of Italy flotilla in Sicily

Portorosa, Italy

2020 Departure Dates:  June 13, June 20,  August 1, September 5 and September 12

Additional special interest flotillas

Exclusively for adults 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 June 20, 2020 and is the same route as the Hvar one week flotilla.

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 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.