To flotilla or not to flotilla is a question asked by many a bareboat charterer. It can be hard to relinquish even a small part of the independence of a true bareboat charter, and visions of bumping hulls with a group of other boats can put a bit of a damper on your vacation plans.

Flotillas, however, can be much different than previously imagined. They offer several incomparable benefits and can in fact make your time out on the water worry-free and completely relaxing. Read on to learn more about the benefits of sailing as part of a flotilla.

What a Flotilla Really Is

Popular in places ranging from the Eastern Mediterranean to the Caribbean Sea, flotillas are a group of sailing yachts that travel together on the same course.




Support when you Need It

When travelling as part of a flotilla you’ll have the support of a lead boat and crew to check weather conditions and help with things like mooring correctly. Even if you’re an experienced skipper it can be a great relief to have help available if something goes wrong, such as crossing anchors with another boat or even just sorting out harbour fees.

Guidance with Routes

Flotilla sailing itineraries are normally planned around the best ports and sights the destination has to offer. Your lead boat’s crew will have insider information and be able to advise the group on the perfect places to go.

Fun for Kids and Adults



As part of a flotilla, there will be people to hang out with on land. During school holidays you can also expect to sail with a good number of kids and teens, which can be fun for the younger members of your family.


The great thing about flotillas is that you can be as participative or independent as you like. The group follows a general itinerary but you set off when you like and at your own pace. You can cruise slowly to the next port or sail hard and get there early.

For more information on flotilla holidays in the Eastern Mediterranean or other destinations, contact your LateSail advisor today.

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