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Flotilla Sailing Holidays

Flotilla Sailing Holidays

Swap the Daily Commute for a 2026 Flotilla Holiday 

Set sail on an unforgettable journey across some of the world’s premier cruising grounds, with expert support and like-minded company every nautical mile.

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

What Is a Flotilla Sailing Holiday?

Flotilla Sailing Holidays

A flotilla is a group of yachts sailing together on a shared route, with support from a professional lead crew. It’s the ideal balance of independence and guidance, perfect for new and seasoned sailors alike. 

Whether you’re navigating solo, with family, or a group of friends, a flotilla gives you the freedom to sail with peace of mind, discover new places, and meet fellow travellers along the way. 

Hear from Claire, one of our experienced base managers, and get a feel for what makes flotilla holidays with Sunsail so special. 

Why Choose a Sunsail Flotilla?

Group

Community on the Water

Flotilla holidays are as social—or as independent—as you like. Make memories with other guests at beach barbecues and snorkelling stops, or sail at your own pace with the comfort of support nearby.

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tracybH9050HC Agana

“My first time on a flotilla holiday and I absolutely loved it. Jesse, Filip and Becky made everything fun whilst making sure we were all safe. They worked so hard so we could relax and enjoy our holiday. I highly recommend Sunsail and if you get Jesse, Filip and Becky as your ‘Team’ then you’ll have an incredible time. We are now planning our next Sunsail holiday for next year!”

janetfutch1 Agana

“We booked one week on the Sunsail Krka Flotilla and one week bareboat setting off from Agana in September.
The flotilla week was stress free and gave us the confidence to relax and enjoy our sailing before embarking on our bareboat adventure.
The Sunsail lead crew were outstanding. Despite some adverse weather conditions they planned a great route, pre booked moorings, organised events and were always prepared to help when needed.
Thank you Jesse, Becky and Filip for an amazing week.”

jvruthie Agana

“Our 4th great sail trip with Sunsail Agana Marina (learning to sail, flotilla and bareboat charters). We really enjoyed our fun trip on the superbly run Hvar Flotilla. Sunsail Agana is a professional, efficient and extremely well run sail base in a beautiful location. We cannot recommend Sunsail Agana more highly and we have already booked to return.”

217MatthewH Agana

“Excellent flotilla made even better by Becky, Jesse and Adam’s humour, experience and good natures. We really enjoyed it and will return (again!). Thanks all. Matthew, Gabrielle, Sonia and Tony”

maryx4ys7 Agana

“A great week of flotilla sailing in Croatia 9n the Hvar flotilla out of Agana marina near Split. Sunsail did not disappoint (again) and the lead crew of Finn, India and Carraig were excellent. Last year we did the Kyrk trip, slightly quieter and more remote but both had excellent island and coastal sailing. This year we had a not-far-off new 42′ yacht that was super spacious and comfy with push button winches and a grill off the back. She didn’t sail quite as fast as the 41′ boat we had last year, but if we come again we’d pay the small amount extra for the 42′ boat. September is a great month for sailing in Croatia – not too hot and good winds. Hopefully we’ll be back!”

X4164HJjonathano Agana

“Finn, Carraig and Elle were fantastic. Great service, communication and support.
Great suggestions for places to see. They were fun and well organized. Croatia is amazing!”

636damianb Agana

“First Flotilla sailing holiday experience for this family with adult children and their friends. We arrived slightly apprehensive that the flotilla model would be too regimented and enforced-bonhomie for our preference, but we need not have worried. The holiday was a great success from start to finish thanks to the excellent lead crew (Jesse, Becky and Filip), the matchless surroundings and weather of Croatia, and the perfectly configured and maintained boat. Thank you Sunsail. Can’t wait to book the next one..”

Flotilla Sailing Holiday Destinations

Discover Mediterranean gems on a serene flotilla sailing holiday. Each destination offers something special – from historical sites and gourmet delights to breathtaking beaches. With six stunning sailing grounds across Greece (Lefkas), Croatia (Dubrovnik and Agana) and Italy (Procida, Sardinia and Sicily), adventure awaits. Each offers incredible sailing conditions, breathtaking landscapes, historical sites, authentic culinary delights and beautiful beaches.

New for 2025 – We’re always looking for new ways to explore world-class sailing destinations and we’re delighted to be expanding our Dubrovnik offering in 2025 with our Libertas flotilla itinerary. Ideal for budding adventurers, you’ll have the opportunity to sail along rugged coastlines, discover hidden coves, admire picturesque harbours and enjoy some of the best swimming, snorkelling and scuba diving in Dubrovnik

Find out more about each destination and book your flotilla sailing holiday today:

Hvar Town, Hvar Island

Agana

  • 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
  • New 2026 Flotilla dates added⛵️⛵️⛵️

Find prices for

Specialist Flotillas

Food and Wine Flotilla

If exploring the world of local wines and traditional culinary treats is your passion, these unique 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.

Whether you want to immerse yourself in Italian culture or experience the wonders of Croatian cuisine, take a look at our Food and Wine sailing flotilla holidays:

Flotilla Sailing Holiday FAQs

Ready to catch the wind? Browse our bareboat, skippered, and flotilla sailing holidays today and start planning an unforgettable escape on the seas. Your next adventure awaits!

What’s included on a flotilla?
  • Fully equipped cruising yacht for the duration of your vacation
  • 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
  • Activity Coordinator is available on the Meganissi flotilla
  • Snorkelling Fins
  • First Morning Breakfast
  • Flotilla Punch Party
  • End Cleaning

*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 on a flotilla?
Do you share a yacht with other people on a flotilla sailing holiday?

No, the only people you will share your yacht with are the people in your party and a skipper if you choose to hire one. All the other sailors in your flotilla will have their respective yachts, ensuring you have a sociable yet still private holiday.

How much do flotilla sailing holidays cost?

The cost of your flotilla sailing holiday will depend on a number of factors, and can start from around £1,775 for two people. Factors may include:

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