The Ultimate Guide to Flotilla Sailing Myths

Flotillas are just ducks in a row, aren’t they? The lead crew shoehorns you into sailing, eating and socializing to a strict timetable, right?


Rumors, myths, and half-truths abound when it comes to flotillas, and we are here to set the record straight and sing the virtues of this unique shared adventure. Sunsail’s DNA is intrinsically linked to the history of the sailing flotilla, and we have honed our approach over the years to give you the most fun you can have afloat. A flotilla vacation grants you absolute independence and complete peace of mind.

What is a flotilla vacation like?

After the daily morning briefing, you’ll slip your mooring and be left to explore the sailing area as you please, reconvening at the evening stop. You’ll mostly stay in village quays and small harbors, 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 organizes 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.

In the beginning…

June 1974: An intrepid group of seven Snapdragon 25 yachts set sail from Aegina,

venturing into the unknown led by skipper Janet Green, her engineer

David Archer and hostie Megan Duncan. This was the world’s first ever flotilla.

Back in the mid-70s, the now-legendary Eric Richardson set up Sunsail’s originator, the Yacht Cruising Association (YCA), and pioneered the flotilla concept. Unable to book a stand for the 1974 London Boat Show, the YCA team took to displaying one of the yachts at Victoria Station, and distributing leaflets outside Earls Court, in the middle of winter. The flotilla sold out within a week.

From the humble beginnings of that initial Saronic voyage, flotilla holidays have since swelled to a worldwide phenomenon, with dozens of routes taking in the world’s best sailing grounds, ranging across the Mediterranean, Caribbean and beyond. Eric and his team were the originators of a flotilla formula that has become a go-to sailing holiday for thousands of people. 


Flotilla sailing combines the freedom to sail independently with guidance from an expert lead crew, who can keep you informed of the best lunch spots, or advise on mooring techniques in tricky harbors.


What is a flotilla skipper?

A steady hand on the tiller, your Skipper is the lead sailor, passage planner, and instructor on the flotilla. All of our skippers are fountains of unrivaled local knowledge. Handy with a wrench, Engineers know each yacht like the back of their hand; they are your on-call mechanic, always ready to help make your vacation run smoothly. Advisors, guides, and event planners, your Flotilla Hosts are there to make sure you get the most out of your vacation.

Do you have a fixed flotilla route for the whole week?

Isn’t flotilla sailing just a bunch of boats following a mother ship around a fixed path all week?

One of the most common misconceptions about flotillas is that you are restricted in where to sail and when. In reality, things couldn’t be further from the truth. Our flotillas are deliberately flexible, giving you support when you need it, and freedom when you don’t. So if the flotilla itinerary lists the next stop as X, but you want to go to Y instead, you can. All you need to do is let the lead crew know that you will be going rogue for the night. And of course, their support is still just a VHF call away.

Sunsail Flotilla
How many yachts make a flotilla?

A flotilla is made up of up to 12 yachts. Enjoy sailing with like-minded people, enjoying the evening social events, as well as the security of having a lead crew to assist if needed.

Flotillas are just for beginners and new sailors, right?

No. It may be hard to believe, but there really is a flotilla route for everyone. A flotilla sailing vacation can be a great way to boost your confidence and let someone else worry about route planning, but we also have carefully selected routes that provide interesting and challenging passages for even the saltiest of sailors.

Do you need qualifications for a flotilla vacation?

We’ve split our destinations into levels, so you can choose your vacation based on your skill and comfort level. These levels are a guide to our sailing areas, encompassing tides, wind, weather conditions, and any navigational challenges that you may encounter:

Level 1• 5 days or 100 miles as a skipper
•RYA Day Skipper with experience in a higher level
• RYA Coastal Skipper
• ICC with experience in a higher level
Greece: Lefkas, Meganisi, Kefalonia & Ithaca flotillasCroatia: Hvar, Vis & Krka flotillasCaribbean: British Virgin Islands 1 & 2-week flotillas
Level 2• 10 days or 200 miles as a skipper
•RYA Day Skipper with experience in a higher level
• RYA Coastal Skipper
• ICC with experience in a higher level
Croatia: Mljet & Dubrovnik flotillas
Level 3• 20 days or 400 miles as a skipper
•RYA Day Skipper with experience in a higher level
• RYA Coastal Skipper
• ICC with experience in a higher level
Greece: Saronic flotilla
Are flotillas just for family vacations?

OK, so flotillas are an ideal family holiday. Doesn’t that mean they’re always full of kids?

Not at all. It’s true that some flotilla routes are great for a family vacation, and in the summer months, they can be a great place for children to make new friends. But, outside of the summer rush, they are generally much more relaxed affairs, with a mixture of couples and groups of friends making up the crews.

Over the years, flotillas have developed and innovated, with new itineraries tailored to suit more mature special interests. These include Food and Wine flotillas focussed on the finer side of Mediterranean life, available in Dubrovnik, Marina Agana, and Procida; and a brand-new Sail By The Cabin flotilla. These are ideal for new sailors, more discerning sailors who can be more flexible with their charter dates, and for flotilla veterans perhaps looking for a new way to explore the local sailing area.

Forced fun?

Flotillas are all about giving you the freedom to enjoy the vacation you want, the way you want it. Just like the route, you can cherry-pick and call the shots on your social plans. This means getting as involved in the flotilla activities as you feel like. You can be the life and soul of the punch party one night and then enjoy quiet family time away from the crowd the next. The choice is yours.

Been there, done that

Perhaps you’ve been on a flotilla before, maybe even in several destinations. Don’t be fooled into believing you’ve seen it all, though. Specialist flotillas add a new dimension to the flotilla concept, breaking the mold to always bring you something new and exciting.

Can I still keep an accurate log?

Yes – in fact, the planned routes tell you the exact distance between ports, and you are free to log any extra sailing you do on top of this yourself. From June 2017 onwards, customers on our Croatian flotillas will also get exclusive access to the Nebo sailing app, to help you log, track and share your voyage and photos with friends.

Which yacht?

Flotillas are no longer limited to a one-yacht-fits-all approach. Fleets vary from small to large and monohulls to catamarans, so there is usually the right yacht to suit your group. For cruising in the Med, there are plenty of nimble 34-41 ft monohulls ideal for navigating tight marinas, while more spacious Caribbean moorings and sailing areas lend themselves to the comfort and convenience of a catamaran, like the award-winning Sunsail 454.

We care about our sailing areas, and we like to keep up good relationships in all our bases. To this end, we have a maximum number of boats per flotilla and cap the number of catamarans in the Med, so we don’t take up more space than absolutely necessary.

Find your flotilla

A flotilla holiday offers an informal, relaxed, and unique experience for families, couples, and groups. We have Mediterranean flotilla routes in Lefkas, Athens, Marina Agana, and Dubrovnik, and have just launched a brand new Mallorca itinerary. You can even spice up your flotilla experience and combine it with themed activities on one of our specialist flotillas. A Sunsail flotilla holiday takes all the fuss out of route planning, and lets you spend more time doing the things you love; sailing in idyllic waters and socializing with your favorite people.



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