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Flotilla Sailing Holidays

Flotilla Sailing Holidays

Set sail on an unforgettable journey across some of the world’s premier cruising grounds, guided by Sunsail’s expert lead crew. Perfect for everyone from solo adventurers to families, our flotilla holidays blend planned routes with exciting social events, offering a communal yet personal sailing experience.

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. 

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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
View Agana

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Bareboat Flotilla

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:

Agana

Agana food and wine flotilla

Marina Agana, Croatia

Ponza

Italian Cuisine Ponza Flotilla

Procida, Italy

Sicily

Italian Cuisine Portorosa Flotilla

Portorosa, Italy

Procida

Italian Cuisine Procida Flotilla

Procida, Italy

Our Flotilla Sailing Fleet

Board our world-class yachts and enjoy a sleek, stylish, and supremely comfortable flotilla sailing holiday. Our fleet is designed to cater to your every need while you explore the seas. Whether you’re setting sail with family, a large group of friends or as a couple, there’s space for everyone to relax, sunbathe, play games and spend quality time together.

Each of our flotilla sailing destinations has a range of state-of-the-art monohulls and catamarans available that are perfectly equipped to navigate the crystal clear waters smoothly. Take a look at our flotilla sailing yachts:

What is a Flotilla Sailing Holiday?

Your group, your route, discover together

A flotilla is a small fleet of yachts that are guided around a destination by a lead yacht, which has a skipper, hostess, technician and activities coordinator onboard.

Flotilla sailing 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 fun group activities, all you need to do is make friends, explore the crystalline waters of your sailing destination and feel your cares melt away.

The best part? You can captain yourself, or if you aren’t a sailor and would rather someone take the helm for you, you can hire a skipper for your adventure. 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.

How do sailing flotilla holidays work?

A common misperception of the flotilla is that you have to sail like ‘ducks in a row’. But a sailing holiday 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 in Sardinia, incredible snorkelling spots in Dubrovnik or searching for the best beach in Greece, 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 are the benefits of Sunsail’s flotilla sailing holidays?

Flotilla highlights

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

Lead crew support

The lead crew is there to support you during your exciting flotilla sailing holiday. 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. With their extensive local knowledge and expertise, 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 so that you can relax, unwind and admire the sensational views.

Skipper

Skipper

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

Hostess

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.

Technician

Technician

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.

Flotilla Sailing Holiday FAQs

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:

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!

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