Opened in mid 1960s.
Damaged by Hurricane Isabel in 2003.
Remains closed today.
Introducing the Islander Hotel – our event namesake
The Islander Hotel inspired the name for Islander Regatta and serves as the start & finish point of the 9-mile paddle adventure. It is located on Gwynn’s Island Virginia situated at the intersection of the Piankatank River and Milford Sound.
The Islander Hotel has a rich history on Gwynn’s Island. Opening in the mid-1960s it has been owned by the same family that originally built it. Debbie Gibson, co-owner of the Islander Hotel and Restaurant, says she and family members are on a quest to resurrect the iconic resort. The once popular getaway closed in 2003 following severe damage in the wake of Hurricane Isabel.
Aerial view of Islander including adjacent marina and Milford Haven Bridge.
Beyond the Milford Haven Bridge, visible on the right is the US Coast Guard Station Milford Haven. Members of the USCG Auxiliary provide water support for the Islander Regatta.
Take a trip down memory lane
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Debbie Gibson
My first job there was as a waitress while I was still in high school and Dad had just opened it. All of his children and many relatives on both sides of the family worked there over the years.
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[Person Name]
Favorite memory of The Islander
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[Person Name]
Favorite memory of The Islander
After brief pre-launch instructions, paddlers enter the water from the beach behind the hotel.
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The Islander Regatta 