A World of Opportunities


Flotillas are a great way to enjoy a sailing vacation in destinations worldwide  (published August 2013)

Just outside English Harbour, Antigua, Jill and I raised the sails on our chartered Jeanneau 44i and I looked at three other identical boats nearby to check how they were doing. With bright white sails set and drawing against the deep blue Caribbean Sea, they all looked good. And with that, we were off.

It was the first day of a flotilla that we were leading through the Leeward Islands and stops in Barbuda, Nevis, St. Eustacia and St. Martin would highlight the trip. Along the way we’d visit pristine beaches, snorkel above beautiful coral, fill our sails with famously consistent trade winds, and socialize while watching the sunset from a different cockpit every night. Sound like fun? It is.

Sailing vacations come in all shapes and sizes. Ranging from bareboat and fully crewed charters to sailing oriented resorts or offshore learning expeditions, there are plenty of ways to get out and stretch your sea legs in-between the commitments and confines of our workaday world.

But one of the easiest and best ways to get out for a sailing vacation is join a sailing flotilla. Having led flotillas in the Caribbean I can attest to the fun, relaxing and exciting time that they offer for novice and competent sailors alike. Here are the basics on sailing flotillas and why joining one might be the right choice for your next sailing vacation.

What is a flotilla?
A sailing flotilla is a group of boats, usually between three and ten, that are led by a support boat with professional captains or instructors aboard. The job of the lead boat is to keep the group moving safely through a cruising itinerary while providing assistance along the way. Flotillas have a semi-predetermined itinerary that the lead boat will sail the group through, making changes as needed based on weather, gear failure, etc.

In general, a flotilla’s itinerary is not very rigorous and offers a vacation that is equal parts sailing, relaxing, sightseeing and socializing. Berths aboard a boat are typically sold individually or by cabin, which makes it easy to join as a single or couple without having to cover the full expense of a bareboat charter.

Also, some flotillas are operated in conjunction with sailing schools or clubs that may offer sail training along the way. As a flotilla leader, I would often start a discussion at happy hour about what went well and not so well for each boat during the day and offered tips based on that. Doing this was great way for participants to learn and share ideas and skills while underway.

Why choose a flotilla?
Besides the fact the flotillas are offered in some of the most amazing sailing destinations worldwide, they are an excellent way for inexperienced sailors or charterers to gain more practical knowledge before setting out on a bareboat charter of their own. While you do not need to be an expert sailor or cruiser to join a flotilla, it is good to have a solid foundation of sailing knowledge before you go. That being said, I’ve found that flotilla crews tend to be made up of sailors with all types of sailing skills and backgrounds.

Often times, a difficult part of putting together a bareboat charter on your own is getting enough family and friends together and coordinating schedules to make it work. With flotillas, you don’t have to worry about the whole crew because it is already done for you. And if you did want to bring a friend or two, you are usually more than welcome to do so. I once led a flotilla where five college buddies booked an entire boat themselves. At first I was a little worried they would stray from the group, but they ended up being a pleasure to sail with and said they would definitely go that route in the future.

Another big plus in choosing a flotilla is that experienced charterers, captains or sailing instructors lead them. This has a profound effect on the safety of the group and can make the experience more relaxing and enjoyable, as you aren’t solely responsible for every facet of the cruising plan, yet you get to learn what goes into it. I’ve routinely had students in cruising classes who were extremely intimidated by the thought of chartering for the first time. A flotilla can be a nice transition into chartering on your own as you are still in charge of the boat, but the leaders are there to facilitate and help along the way.

The truth about bareboat charter companies is that they don’t let just anyone charter any boat, anywhere, at any time, which is a good thing. Different cruising destinations call for diverse sets of knowledge, so if you want to charter in the South Pacific but aren’t qualified, doing a flotilla in that area first will certainly help. The same can be said for size and type of vessel. If you really want to charter a big catamaran but have never sailed one before, going on a catamaran flotilla would be a great way to show charter companies you are up for it next time.

Just like everything in life though, flotillas certainly aren’t for everyone. Getting placed on a boat with people you have never met, hoping your personalities mesh, and trusting their sailing experience and judgment can be an intimidating part of choosing to join a flotilla. But that can also be one of the most memorable and rewarding parts of it too. In my experience, sailors are like-minded people and those who choose to join a flotilla will more than likely become fast friends rather than foes.

IMG_0433    Choosing a flotilla for your sailing vacation is one of the easiest ways to go on an inexpensive charter in a fun, relaxing and rewarding environment. Sailing in a group of boats with other experienced sailors will provide a boost in confidence and you will likely meet friends along the way to charter with later. Plus, you’ll find yourself cruising in one of the world’s best charter destinations, which isn’t so bad either.


There are many ways to get involved with flotilla cruising. You can go directly to the charter companies that often host flotillas and join one of their programs or you can go through a privately sponsored organization, such as your yacht club, that negotiates its own flotilla rate with the charter company.  Here are the charter companies that host most flotilla charters:
Sunsail started out as a flotilla charter company in the Mediterranean and grew to be a worldwide charter company. Today they run 32 unique flotillas around the world and can customize flotilla vacations for you and your sailing friends or club. Check it out at www.sunsail.com/flotilla-sailing.
The Moorings is not as involved with flotilla chartering as its sister company Sunsail, but they do work with organizations to put together custom flotillas. One of the most popular is a medical sailing seminar called MED Sail for doctors who want to earn CME credits while sailing in the B.V.I. Learn more at www.moorings.com.
Kiriacoulis Yacht Charters in Europe offers flotilla charters in Greece that will appeal to those who want to explore farther from home among some of the best and most interesting islands in the world. www.kiriacoulis.com.