2026 Islander Regatta
The Islander Regatta had been on my radar for a few years, and I finally had the opportunity to participate. The regatta is a human-powered circumnavigation of Gwynn’s Island in Mathews, Virginia. I frequently sail and paddle around Gwynn’s Island, but making it all the way around in a small sailboat or on a paddleboard is usually a little farther than I’d want to do on my own. Doing it as part of an organized event made it a great opportunity.
The event started from the Islander Hotel at 8:00 a.m. on Saturday. The hotel is another place I’ve passed countless times by both road and water but had never visited. It operated until 2003, when it was heavily damaged by a hurricane. The building and surrounding property have seen only occasional use since then.
Around 80 participants launched from the beach in a variety of human-powered boats, including sea kayaks, recreational kayaks, paddleboards, rowing shells, and other craft, all setting off on the counterclockwise trip around the island.
After leaving the beach, we rounded the hotel property and entered the channel leading toward the bridge. Once under the bridge, we headed into Milford Haven on the west side of the island. As the water opened up approaching Hole in the Wall, the wind increased and the longer fetch built up small waves that struck from the side. That meant a lot of paddling on the left side to compensate for the wind and waves.
At the southern end of Gwynn’s Island, participants had a choice. Some elected to portage across the beach, cutting about a mile and a half from the route. Roughly a quarter of the boats, including mine, continued around the entire island without taking the shortcut.
Once we reached the eastern side of the island and entered the Chesapeake Bay, the shoreline provided more protection from the waves, and the wind eased considerably, especially along the stretches lined with trees and houses.
At the mouth of the Piankatank River, we turned west into the wind for the final leg of the trip. The last 2½ miles back through Hills Bay to the Islander required paddling into a light headwind and small waves before returning to the finish.
