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The Last US Virgin Island, Water Island

Updated: Jan 23, 2021

We knew very little about Water Island before this trip. I knew it existed and had an old friend that lived on a sailboat there but did not plan to visit during our trip. While eating at a restaurant, we started chatting with a local that said we should check out Water Island. The next morning, we picked up the anchor and made way to Honeymoon Bay on Water Island. Pulling in, the water is a beautiful turquoise blue with a white beach. Although the bay was full of boats, the beach wasn't too busy. Just outside the bay is a great snorkeling and diving on reefs and a wreck. When we arrived, I messaged our friend, Kevin, who was already hanging out on the beach. Kevin grabbed his friend, Kathleen, and we went to explore the old fort on her golf cart.

As we arrived to the top of Flamingo Point, Kathleen shared that she spent two hurricanes in the fort with her family and neighbors in the 90s. After a scenic photo, we entered the fort and continued down a corridor. There is a labyrinth of hallways to explore, but we went up! We climbed a ladder and had to barrel roll out of the bunker before going to a different entrance that we repelled down in to! We had fun exploring the WWII fort that never saw a battle, yet if walls could talk, I can only image the history it has seen on this 500-acre Caribbean Island.

Kathleen has lived on the island since the early 90s and owns a picturesque home on a hillside overlooking Flamingo Pond. She told us her story of Hurricane Irma. She was alone in her home with her dog and cat. Her porch roof and railings were ripped off, and bedroom windows and living room sliding doors shattered. Listening to these stories from the different people we meet, always brings tears to my eyes. They all have the same thing in common, “I thought it was the end.” She is still fighting with insurance and has boards over some windows and doors, but Kathleen is strong and her home is still solid and absolutely beautiful!

Thanks to, I learned a bit more about the fort and Water Island. In 1917, when the US bought the Danish West Indies, Water Island was not included in the purchase. During World War II, the US Military began construction of a bombproof fort on the privately owned island, and by 1944 the US Department of Defense acquired the land. Although construction of the fort was never completed, it was named Fort Segarra after a decorated WWI veteran. The Army eventually vacated Water Island and turned it over to the St. Thomas Development Authority who leased the land to Water Island Inc. Water Island Inc. was made up of Walter and Floride Phillips, and partners, who build a hotel from the existing barracks. Water Island was Walter and Floride’s home and passion until their death in the mid-90s. Over the years, the hotel was remodeled, rebuilt and changed ownership, but in 1989, Hurricane Hugo devastated it beyond repair. It wasn’t until December 12, 1996 that Water Island became part of the US Virgin Islands and residents were finally able to own their own land.

Returning back to Honeymoon Beach that evening, a projector and movie screen were set up between two palm trees. We watched ‘Rampage’ on the big screen with a backdrop of mastlight stars in the bay.

With each island we visit, we are adding to our collection of short stories that are the making up this chapter of our lives. To learn about charters on board Kuma Too, visit

Until next week, Happy Sailing!

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