Flotilla Information & Schedule


WHAT is it?

WHO Can Participate?

WHY You Should Go?

What's NOT Included?

HOW Does It Work?


British Virgin Islands

November 14 – 21 , 2021 (Sunday – Sunday)


Pearl Regatta – April 2021 (Saturday – Saturday)

Croatia Dalmatian Coast

June 18 – 25 , 2022 (Saturday – Saturday)

“A Flotilla should be fun, with lots of activities and well organized. It’s a great way to make new friends… sort of a grown-up version of summer camp!”


Flotillas, rendezvous and other boater group trips are becoming more and more popular worldwide and increasingly diverse. Most having specific activities and themes depending on interests. Made up of a fleet of boats with a lead boat and crew on a planned route and schedule with fun group activities and interesting stops over the course of a week or longer. The flotilla types based on activities may include sailing instruction, scuba diving, regattas, yoga practice, music concerts and all sorts of parties to attend. Some are adult-only and others geared for families with kids.

The concept for a recreational boat Flotilla was developed by Sunsail over 35 years ago, and they describe it as the perfect balance between independent boating, security of a group with a host of social options. This type of event is organized by experienced travel planners and crew incorporating a vast selection of luxury sailing yachts at key destinations including power catamarans for the motor yacht enthusiast.


Going on a Flotilla is perfect for singles, couples, families and groups. Beginners, novices and experienced sailors all welcome. Many times, the organizers help coordinate and match people on boats based on their experience and requirements. A yacht charter specialist will have several luxury sailing yachts to offer but also can include power catamarans for the powerboat enthusiast.

Are you a social butterfly or an independent adventurer? However you like to sail or whatever you prefer to do, the freedom to choose is yours on a flotilla. Whether you’re a fan of parties on the beach and great conversation over dinner or just looking for a little friendly competition, you’ll find a flotilla the perfect balance of solo adventuring and social sailing.


Whether you’re new to sailing or a keen bareboat sailor, “why go on a flotilla?” will probably be the first question on your mind. Quick answer, “the experience!”. You’ll be able to enjoy all the freedoms of an independent yacht charter with the added bonus of a set sailing route to follow a supporting Lead Boat and a great social atmosphere with your fellow sailors.

There’s a range of benefits of a Flotilla vacation, from guaranteed moorings to inclusions such as fuel, water, ice, the cost of your insurance, excursions, tours, events and included activities. The Lead Boat crew is there to support you. You can be as independent as you like with the confidence that they will be there to lend a helping hand when you need it. They can also recommend the best anchorages, harbors, restaurants and places to visit, ensuring that you make the most of your time of vacation.


Provisions like food and drinks are not included, however we can recommend places to purchase them. Mooring and dockage fees are typically not included and the boats are not equipped with life jackets for children under 10 and there are no beach towels. The yacht security deposit and damage waiver is also an extra fee depending on the level of coverage.


Every day you’ll be briefed on the destination for the day, as well as weather updates and any must-see spots along the way. They’ll help you cast off in the morning and then sail direct to the next destination so they can be there to help everyone moor up at night. But after that you’ll be left to explore the high seas yourself, whether you’re looking for some exciting sailing or searching for the perfect beach. You can sail with confidence knowing that any assistance from your Lead Crew is only a VHF or phone call away.

You’ll be staying mostly in village quays and small harbours, with the choice in the evening to explore on your own, or meet up with the rest of your Flotilla for dinner and stories. The Lead Crew will also organize social events like BBQs on the beach, Punch Parties and an End of Week Regatta so you can get to know the people you’re sailing with. The flotilla costs put on by charter companies will vary up to $1200 for the larger boats. The club type of organized events are usually at no cost because volunteers put things together.

There is usually an arrival and orientation get together on the first evening or first morning breakfast. Get to know your Lead Boat crew and fellow Flotilla sailors before you head out on your first day of sailing. This is the perfect chance to make new friends for the week – maybe you’ll even make arrangements to meet up at dinner!

During the week, a Flotilla Punch or Beach Party is a great opportunity for you to meet up with your Flotilla again, sharing stories, tips and tricks with each other over good food and a drink.

Towards the end of the week, perhaps a regatta if you’re feeling competitive. This is your chance to show off your yachting know-how and challenge your Flotilla companions to a race. Use all your sailing skills and do your best at this end of week regatta!

Of course, these aren’t your only options, since the social life of a Flotilla relies on the sailors themselves. May flotilla groups meet up in the evenings to share meals and stories, though if you prefer peace and quiet that’s easily available too!


Join Our Next Flotilla!

Have any questions? Contact us!

1 855-231-4111

7 Days A Week: 8:00AM - 8:00PM

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