Islander Regatta 2023

Annual 9 mile paddling event for non-motorized craft. Circumnavigating one of Virginia’s few inhabited islands: Gwynn’s Island in Mathews County.

With its origins as a fun summer challenge for a group of friends, the Islander Regatta is opening its door to more participants. 2023 Event Maximum is 200. The Course. The Islander Regatta course follows the outline of Gwynn’s Island, which has been described as having a “shark fin” or triangular shape. Paddlers will launch from the beach of The Islander Hotel (see venue section for more info) and proceed counter-clockwise under the Milford Haven Bridge into Milford Sound.

The Venue. The Islander Hotel is a landmark on Gwynn’s Island – visible for miles from the water and one of the first sights when you cross Milford Haven Bridge onto the island. A once popular destination resort, it is still owned by the same family who built it in the mid 1960s. The Islander suffered extensive damage during Hurricane Isabel and was forced to close.

Logistics. Safety, Support and other important Stuff. Hosting an outdoor event – in particular one on the open water – requires thoughtful planning & preparation. The Islander Regatta is supported by the US Coast Guard Auxiliary Flotilla 66, which is headquartered at the USCG Station at Milford Haven. Providing shallow water support are volunteer boaters from Mathews County – all of whom are connected via radio communication with the Race Directors throughout the event.

Registration cost is $65 per person not per boat. Tandem kayaks, 8-person racing shells, paddle boats and even dragon boats (!!) are permitted as long as they are human powered, non-motorized. Each paddler must register separately (must be 14 or older).

IMPORTANT NOTE (updated June 12) - custom windbreaker order has been submited (6/12 PM). We have a limited number of extras but you may not get the size that you requested if you've registered after that date.