Island Watersports

HistoryCarefree Boat Club was founded in Virginia in 2002. Since then Carefree Boat Club has become the premier boat club operator in the US and Canada and we are continuing to grow. Everything we do is based on operating at the highest standards in the industry. Our membership ratios are strictly maintained (ten members for every one boat), as are the quality and upkeep of our boats. Our goal is to provide our members with the highest quality boating experience, to provide a safe and easy intro into boating for new boaters and to offer the best variety of boats and ports possible. Our ultimate goal is to make boating fun, easy and affordable. The Ocean City location was founded in 2018 and sits next to Harpoon Hanna's off Route 54 in Fenwick Island and works directly with Island Watersports dealership for boat sales and service, so a supply of boat inventory isn't an issue and if a boat needs repairing, service prioritizes our boats to get them back out on the water as quickly as possible.SpecialtiesThe Carefree Boat Club of Ocean City is a private boat club that is available to only members. Members enjoy unlimited access to a fleet of brand new boats each year that are equipped with the latest and greatest in electronics and upgrades. Our staff handles all of the preparations needed in boating such as maintenance, boating insurance, storage. The boat is at the dock, cleaned and fueled up awaiting our member's arrival. The club also offers free on-going training to all of our members. New to boating? No problem. All members receive free on the water training with our certified captain on the boating basics such as anchoring, docking, basic operation, and navigational instruction of our waters. Additional advanced training on jet boats and offshore twin engines are available to our members as well. The club offers a variety of different boats ranging from Berkshire pontoon tri-toon models, Scarab jet boats, twin engine offshore fishing vessels, ribbed inflatable boats, as well as v hull Four Winns deck boats. Members enjoy spending the day at Assateague Island, doing watersports in the Saint Martin's River, visiting on the water Ocean City restaurants, fishing and crabbing, and cruising the bay. Several of our fishing boats are equipped with live wells. The club operates 7 days a week for members reservations during the season (Memorial Day - mid October). Our Carefree Boat Club members have access to reciprocal boat reservations over 115 locations nationwide.