Course Map

Google map of Gwynn’s Island Virginia showing the 9-mile paddle route

The Islander Regatta course follows Gwynn’s Island in a counter-clockwise direction from The Islander, which is indicated with the green “Start” block.

Milford Haven aka Milford Sound

After departing from The Islander Hotel location, we’ll pass under the bridge and into Milford Haven; there are plenty of inlets to explore on this side of the island if you still have energy after the full circumnavigation. The US Coast Guard Station at Milford Haven is just past the bridge – the USCG Auxiliary Flotilla 66 provides water support for the Islander Regatta.

Chesapeake Bay portion

The Islander Regatta course continues to follow the island coast around to the Chesapeake Bay – you’ll notice more winds and currents on the Chesapeake Bay side of the island. You’ll pass the Gwynn’s Island Sun Retreats Campground as well as a lot of beautiful homes for approx 3 miles on the bay side.

Piankatank River/ Hills Bay

The final section takes you back to the Islander Hotel on the Piankatank River where the wind & waves are generally calm. Those are the three main sections of the entire paddle (Milford, Chesapeake, Piankatank); zooming in on the center of the map, you’ll see the Museum marker – for reference, that is next to the Gwynn’s Island Civic Center, the location of the Annual Gwynn’s Island Festival which occurs on the same day as the Islander Regatta. See More Local Activities.


Important Information about course time limits

The Islander Regatta is designed as a challenge, achievable by the majority of paddlers, even with limited experience. We expect a variety of skill levels to participate but it is not intended as a race. We have created some time limits on the course with safety in mind. Our water support crew – from the USCG Auxiliary and local boaters – are available during this specified time period only.

Overall Event Time Limit is 5 Hours. To help maintain that limit, paddlers who are not able to reach certain checkpoints – details below – by a designated time will be asked to either turn around or head to shore and pull out of the water.

Checkpoint #1 in 2 hours where Milford Sound ends & you turn onto Chesapeake Bay side. Participants who reach this point in > 2 hours should turn around and return to the start/ finish point at the Islander Hotel.

Checkpoint #2 in 3 hours – this is a designated pull off/ rest area along Chesapeake Bay side. Participants who reach the first rest area after 3 hours should discontinue the circumnavigation. A support driver will shuttle you back to the start/ finish area.

Checkpoint #3 in 4 hours where Chesapeake Bay ends & you turn onto Piankatank River side. Participants who reach this second rest area after 4 hours should discontinue the circumnavigation. A support driver will shuttle you back to the start/ finish area.


How long does a “typical” circumnavigation take?

As mentioned, we expect & encourage a wide variety of skill levels to participate in the Islander Regatta – and we’ve had some relatively new paddlers take on the challenge in previous years.

  • The fastest completion of the 9-miles was just over 2 hours
  • the average is 3 hours, and
  • our longest finish came in just under 4 hours.

The time limits mentioned are certainly achievable, even for the less experienced. The rest stops will have snacks, drinks and porta potties – just keep an eye on the clock if you are near the time limit for that point.