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The Fleet

Boats of SailUSVI


    The Legacy Continues...
Wayward Sailor is an antique Islander29
manufactured by Wayfarer Yacht Corp. in 1966. She has been sailing the waters of the VI for some 40 years of her sea service captained by none other than the legendary Capt. Phil Chalker (dec. 2021) a naturalist and avid sailor. The wayward Sailor has now joined the SailUSVI fleet under new ownership since Phil's passing. We sail on in his memory and honor. Join us aboard for an authentic Caribbean experience!


   Two Legacies Combined:
The Athenian is a classic Pearson 385
"Space Ship" built in 1983 by Pearson Yachts.
Formerly known as "Spree 2" when she was owned and operated by Capt. Bob Reedy (AKA Spree Bob) for nearly 15 years out of Cruz Bay St. John, USVI. Bob has since retired and now sails his new boat "Spree 3" around the Great Lakes. 

The Athenian can attribute her name to my late Father, Capt. Richard A. Benson, owner and operator of the 84' wooden sailing ship, the "Goddess Athena". Richard was lost at sea in 2017 during Hurricane Irma. The loss is still a sore subject for his son and aspiring Captain Daniel R. Benson. With each day of sailing, his memory is honored. 

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