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Offshore Sailing and Cruising with Paul Trammell

Offshore Sailing and Cruising with Paul Trammell

Tim Skillman,"Looped," Sailing in Search of a Mid-Life Awakening

Offshore Sailing and Cruising with Paul Trammell · Sep 21, 2026 · 1:16:27

0:001:16:27

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Tim Skillman is a long-time sailor and author of "Looped: from the Staits of Mackinac to the Bitter End," a book about his mid-life-crisis journey from the Great Lakes down the Illinois, Ohio, Tennessee and Tombigbee  rivers to the Gulf of Mexico and on to the Virgin Islands on a Cheoy Lee 53.

We talk about growing up racing small boats in Michigan, buying an Erickson 46, the secret to not getting burned out on maintaining a boat, lunch with Richard Branson, meeting his future wife on the beach, the journey down from the great lakes to the Gulf of Mexico, walking away from his career and family, dealing with the locks and river traffic, why he avoided the Missisippi River, entering the Gulf of Mexico, Key West, crossing the bank between Key West and Nassua, sailing to a foreign country for the first time, a shark encounter while spearfishing in The Bahamas, the Dominican Republic, guns on the boat, the Virgin Islands, an awakening, the San Blas Islands, the Guna people, aliens, and more.

Photos and links are on the podcast shownotes page

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Episodes: Offshore Sailing and Cruising with Paul Trammell

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