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Flotilla Sailing Holidays

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, a set sailing route, and social events. Captain yourself, or if you aren’t a sailor or would rather someone take the helm for you, you can hire a skipper for your adventure.  

Flotilla holidays offer an informal, relaxed, and unique experience that takes the stress out of chartering. With a set itinerary (weather-dependent), organised moorings each night, and even fun group activities. Perfect for families, couples, and groups across 4 stunning sailing grounds in Greece, Croatia (Agana and Dubrovnik), and Italy (Procida, Sardinia, and Sicily).

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

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

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.

Flotilla highlights

  • Set sailing route
  • Lead crew support
  • Guaranteed mooring
  • Social evenings
  • Beach barbecues
  • Punch parties

Flotilla Destinations

Hvar Town, Hvar Island


  • 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

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Special Interest Flotillas

Food and Wine Flotilla

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 more insider knowledge read our Guide for sailing the Mediterranean.

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 directly 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 organises 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

*Fuel is not included on our specialist flotillas in Italy 
**In place of Flotilla Punch Party will be a Gin and Tonic party. Lead crew consists of a Skipper and Technician.

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.

Flotilla Sailing Holidays


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.

Flotilla Sailing Holidays

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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