Kip Koolage USCG 100T MASTER of SAIL & POWER

Kip Koolage is an experienced Captain with a long history in the maritime industry. Growing up on the Severn River, Kip began a 50 year sailing career racing penguins and 420s as a junior member of Annapolis Yacht Club.  At 15, Kip was hired as a sailing instructor for the Annapolis Sailing School and soon thereafter won a national championship title in the schools Rainbow class.

Sailboat racing was a passion over the next 40 years and spent as captain and crew on a variety of racing sailboats ranging from 22’ to 50’ racing around the buoys and offshore in the waters of the Chesapeake Bay, Newport RI, Block Island, Marblehead, 

Florida Keys and more. During the same time, Kip was also employed in the trades as a Sailboat Rigger, Yard Foreman, Service Manager, Marina Manager, Tow Boat US Captain.

For nearly 25 years since acquiring his USCG Masters, Kip has moved a long list of clients boats, without incident to and from dozens of east coast and tropical Caribbean destinations. In short, Kip has spent the majority of his life on the water and uses that knowledge and expertise to safely and efficiently deliver power and sail boats anywhere along the entire US East Coast & Caribbean.   

Kip (now based in Ocean City, MD) holds a 100T USCG Masters including Sail and Commercial Tow Endorsements. He is a certified American Sailing Association Instructor and current Member of the Chesapeake Area Professional Captains Association.  

Currently during the summer months Kip is a Charter Captain onboard a 100 passenger tour boat. And from May through September, logs over 120 days on the ocean every season.   Throughout the fall months and before spring commissioning Kip is active delivering boats for individual owners, charter fleets, brokers and marine service providers. 

 Kip relies on two quotes learned from past mentors to guide every delivery: 

- “If you fail to plan - then plan to fail”. 

- “You get what you inspect - not what you expect”.