Reginald Van Winslow is a former captain of the Screaming Narwhal and later crew member under Captain Guybrush Threepwood. Van Winslow is known for his unusually positive disposition (even when suffering massive internal hemorrhage from having a bomb explode near him) and is known for his love of maps, to the point that he refuses to go anywhere without having Guybrush point to it on the Narwhal's map. He is also shown to be sexually active, a trait which disturbs Guybrush, and apparently has a relationship with the Vaycaylian Anemone (the logistics of which baffle Guybrush).
On a pursuit after a pirate who made off with his booty, Winslow was caught in the wind current of Flotsam Island where he presumably crashed into the reefs, stranding him on the island the same as all the other inhabitants of Flotsam. After a while living on Flotsam, Winslow became captain of the Screaming Narwhal after by tradition somehow knocking off the previous captain. Ever since then, he never leaves the Narwhal in fear that it may be taken from him, though he claims that no-one on the island has been brave enough to challenge him. At some point before being drawn into Flotsam Island, Winslow once journeyed round the Jerkbait Islands in the hold of Captain Liverbottom's trader ship, and served as a cabaña boy in Borneo. He also worked at and became a master of haiku in the Sashimi Islands, learned the expression of "sexyfish" while on a tour of the exotic Limbo Islands, once met a (rather) provocative dancer in Booty Island, and bought Old Brute Pirate Deodorant from an apothecary in Woodtick.