Myth-Busting Flotillas

Whether you have a family who’s new to sailing or are an old salt who’s ready to try a new cruising ground, a Sunsail flotilla sailing vacation in the Mediterranean might be just what you need.
Sunsail charter
Explore some of the world’s best cruising grounds with the support and reassurance of a Sunsail lead crew, set sailing route, and social events. Patrick Bennett

Did you know that one of the most popular ways to go on a sailing vacation in the Med is to join a flotilla? It’s a relatively novel concept in the North America and Caribbean charter markets, but if you want to expand your sailing horizons, it might be just what you’re looking for—whether you’re a newcomer to sailing or an old salt.

Curious? Let’s look at what a Sunsail flotilla is and what the experience is like by debunking some misconceptions.

What is a Flotilla?

Sunsail pioneered the flotilla charter concept in the 70’s and has since welcomed tens of thousands of sailors from all over the world to this unique social-sailing experience. Celebrating 50 years in business in 2024, Sunsail is the go-to charter provider for bareboat sailing and flotilla vacations. The company’s mantra is that it is run “by Sailors, for Sailors”, and this passion for sailing shines through every part of the customer journey.

Sunsail flotilla
Flotillas are for sailors of all experience levels. Sunsail flotillas are primarily available in the Mediterranean at bases in Croatia, Greece and Italy. Sunsail

 In its most basic form, a flotilla is a group of yachts chartering together with some extra support and a structured itinerary. What does this look like in practice? A Sunsail flotilla typically lasts one or two weeks, and has about eight to 10 participating boats along with a lead boat, which has a skipper, technician (to help with any mechanical issues on the boats) and host. Depending on the route and timing, there might even be an activity coordinator just for kids.

What makes the experience special is all the details—such as sailing routes, moorings and marina stays—are worked out ahead of time, and there is a variety of optional planned activities. Each morning, the flotilla skipper hosts a chart briefing to go over the day’s journey and any weather updates, as well as places of interest to visit. As the boats arrive at the destination, the lead boat crew is there for assistance with tying up at the night’s mooring or dock. The flotilla host plans events, including beach barbecues, punch parties and group dinners, so you can get to know your sailing group. The host can also direct you to the best restaurants, beaches and local attractions.

Sunsail flotillas are primarily available in the Mediterranean at bases in Croatia, Greece and Italy. Each flotilla destination has a unique itinerary, so you can choose something that interests you. Want some action? Try kitesurfing on a Lefkas, Greece, flotilla. Is history your thing? You’ll find an abundance of historical sites to visit on Sunsail’s flotilla route from Dubrovnik, Croatia. For something a little different, Sunsail also offers themed food-and-wine flotillas in Italy.

Learning to sail
Many recently certified sailors enjoy the structure and additional support flotillas offer, which allows them to get a bit steadier on their sea legs before doing a solo bareboat charter. Sunsail

“Our food-and-wine flotillas have proved incredibly popular,” says Josie Tucci, Sunsail’s vice president of sales and marketing. “We’ve redone our Croatia itineraries to capture even more of the coastline’s natural beauty and architecture, and we recently added another food-and-wine flotilla option in Italy. Our goal is to help Sunsail guests experience the very best of the region, as well as authentic local cuisine, at every stop along these itineraries.”

Still have some questions? Let’s bust some myths about flotilla charters!

Myth 1: I’ll be sharing the boat with strangers

Not true! Each boat on a Sunsail flotilla is booked and sailed individually, just like it would be if you were doing a bareboat charter. Just pick your crew and choose your boat! Alternatively, if you’re new to sailing (or just want to relax more), you can hire a skipper for the duration of the flotilla. Or you can turn the adventure into a real learning experience through the Sunsail Flotilla Hero program, which provides Royal Yachting Association instruction, allowing you to earn certification while on vacation.

Myth 2: We will have to sail in a line from place to place and won’t have any freedom to do what we want.

This is a common misconception about flotilla charters, but nothing could be further from the truth! While there is a set flotilla itinerary, charterers are free to sail as they wish between destinations many itineraries include a free day, allowing crews to set their own agenda. Any planned activities, meals or excursions are optional.

Myth 3: Flotillas are only for beginner sailors.

Flotillas are for sailors of all experience levels. Just like a bareboat charter, however, the skipper of the boat needs to be qualified. If you’re planning on a Sunsail flotilla in the Med, you will need to have certifications through ASA 104 (Bareboat Cruising) or US Sailing Bareboat Cruising. After that, you can apply for an International Proficiency Certificate, which is the US equivalent to the International Certificate of Competence typically issued by the RYA.

Sunsail flotilla
Sunsail offers specialty flotillas that cater to families, groups, solo travelers and specific interests. Sunsail

Many recently certified sailors enjoy the structure and additional support flotillas offer, which allows them to get a bit steadier on their sea legs before doing a solo bareboat charter. Are you an old salt but new to chartering in the Med? A flotilla is an excellent way to get familiar with a new cruising ground. Cruising with kids? Sunsail flotillas are great for families and provide opportunities for the kids to make some new friends.

Sunsail Flotilla vacation
Aboard a Sunsail Flotilla vacation you begin the week as complete strangers, but leave with a lifetime of memories with lifelong friends. Sunsail

Ian Pedersen, Sunsail’s senior marketing manager, offers one piece of advice for someone looking to try their first flotilla: “Keep an open mind, and embrace the social aspect of the flotilla concept,” he says. “People from all over the world and all walks of life come together to celebrate a week on the water, and that is where lifelong acquaintances and friendships can be made. You begin the week as complete strangers, but shared experiences like this really have a way of bringing people together.”

Start booking by visiting or speak to a Sunsail vacation planner directly by calling 800-734-5254.