A group of iguanas is called a “mess”. A group of sharks is a “shiver”. A group of rhinoceroses is a “crash”. A group of boats? A FLOTILLA!

As a general rule, a small group of any kind of ship is a flotilla. Typically, they are all the same kind of ship and maybe a part of a larger fleet. A lot of people think of the word in the context of naval flotillas, but in our world, “flotilla” conjures up a very different image.

What is a flotilla (as a sailing vacation)?

Basically speaking, a sailing vacation flotilla is when a group of boats (often sailing charter yachts) go on a group vacation together. This typically entails starting at the same location, following the same trip itinerary, and anchoring at the same places overnight. You could even think of it a little like a road trip with a caravan of RVs, but instead of RVs, we’re talking beautiful sailboats and instead of a dusty highway, you’re looking at crystal-clear waters. There are multiple ways to join a flotilla (bareboat, hire a skipper, cabin charter), but the gist is that you’re all in it together!

Sailing Flotillas can be a great way for sailors of varying levels of experience to explore new destinations, learn from each other, and often learn from hired captains or instructors in the flotilla. It can also be a way for sailors to participate in organized events onshore and on-the-water, or to simply enjoy the camaraderie of meeting and sailing with others.

Why do people choose sailing flotillas?

  • Comfort

    If you haven’t spent a lot of time chartering boats, especially internationally, a flotilla gives you a little piece of mind. You’re not alone. There are like-minded people coming along with you and you know that the trip is planned. Any troubleshooting can be done by multiple people and you have the added security of having other sailors nearby. There’s often a local skipper (always, for our trips)  in the group, so you have a built-in tour guide as well.

  • Local Expertise

    Speaking of tour guides, flotillas are a great way to experience locations and adventures you may never have known about without a group and a local there to guide you. Even though people new to vacation chartering often choose flotillas, a lot (and we mean a lot) of people are repeat flotilla-joiners. We would argue that you’ll learn way more on a flotilla sailing vacation than you would sailing on your own.

  • New Friends

    Meeting new people is basically the number one reason that people keep choosing flotilla vacations. For families, having other kids around is key to them really embracing the experience, but we find that everyone ends up loving the relationships they build while on a flotilla.

  • Cost Savings

    Participants often can save money by joining a sailing flotilla. While there may be additional costs associated with joining a flotilla, such as organizing fees or shared resources, the overall cost can be lower because multiple boats are chartered at a discount, and there may be options to rent just a cabin or crew on someone else’s boat.

What’s a Typical Flotilla Example?

Last year, we did an awesome sailing flotilla in Central Croatia and documented it so that you could see what it would be like! You can’t exactly see how much fun we had, but at least you’ll get an idea of how it’s a mix of structure (so you don’t need to plan quite as much as if you were going by yourself) as well as free-time (we always leave a ton of room in itineraries so each person can have the vacation they want).

So, what is a flotilla, really?

It’s a chance to meet new people, have the confidence to explore a new place, and learn a heck of a lot along the way. Want to learn more? Check out our post BENEFITS OF FLOTILLA SAILING to learn more….

If you’ve been dreaming of joining a flotilla, but you aren’t yet qualified to charter a boat, check out our Bareboat Charter Master Bundle.

Where NauticEd comes in

We are, first and foremost, sailing education experts. We pride ourselves in turning people simply interested in sailing into safe and competent sailors. After that? We want you to have a lot of fun! Our team members have sailed in countless flotillas and continue to do so, mainly because we have such a great time. We also are sailing charter specialists and are happy to help you book your next sailing vacation. The charter companies we work with have all been vetted by us (we’re picky) and our team is available to give you insider knowledge from our many years of experience.

Curious about where we’re going next? See our Upcoming Flotillas here!

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I find myself drawn to any project that allows me to learn and use my creativity to solve problems - and sailing tops my list!
Trisha Evelyn
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Last updated on May 10th, 2023