I need to interrupt my usual blog of St. John memories to pay tribute to a friend who passed away September 17, 2021, Captain Phil Chalker.
Captain Phil owned and captained his boat , ‘Wayward Sailor’ which means: “in search of one’s own destiny“. With over 30 years of sailing in the Caribbean and a marine naturalist, his charters for tourists on St. John was one of the best experiences anyone could ever want! He would anchor and join his guests in the ocean to give a guided snorkel tour or if you wanted a wedding out on the water, he was ordained to do so!

I met Captain Phil through a mutual friend , Trista Sigler. She had been friends with Phil for many years, was a great help to Phil after Hurricane Irma and she even helped crew on many of his charters. Even though he could be a salty sailor at times ( hey, when I met him he was in his eighties and still going strong!), he was very professional and informative on board.


I was blessed to go out with Captain Phil, Trista and just one other friend on his sailboat, snorkel a bit then visit his home on Lovango Cay , which is a 114 acre private island one mile north of St. John and only accessible by water. Once we landed on Lovango, I saw how Phil stayed so fit. He lived on the hillside and to get to his home you had to use a rope guardrail to pull yourself along the treacherous pathway. Crazy!

When we finally arrived (whew!), it was such a treat! Beside the spectacular view, his home was a great example of simple St. Johnian life. One huge room housed his bed, living space and kitchen with a small bathroom off the side. There’s even a tree that was growing inside the living area (he had planted years ago in a large pot) and he would decorate seasonally!! Plus a great long deck outside to lounge and take in the view of the ocean and St. John and all the way to the BVI😍



We sat and shared a great feast we had made and brought for Phil as a thank you for graciously giving us such a great day on his sailboat and the rare pleasure of visiting his home.
As Trista and our other friend (she’s camera and social media shy) were getting to know each other and taking in the view at one end of the deck, it gave me a chance to get to know Captain Phil better. He regaled me with his sailing stories, his passion for the ocean and sea creatures, and I found out he was even a model in his younger years!! ( I wish I had the picture he showed me because he really was a handsome man!)


Sadly, this would be last time I had any real interaction with Phil except for brief hellos and hugs passing each other in Cruz Bay as he was meeting his boat guests for charters.
Good bye , Captain Phil, and may you have fair winds and following seas on your journey to your eternal home! You will be greatly missed!

Captain Phil was an icon. A great man who truly loved the sea. I’m so happy to say I was his friend. He is deeply missed.
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