Podcast Episode

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

Offshore Sailing and Cruising with Paul Trammell·Paul Trammell·2 October 2026·1h 16m

About this episode

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 Support the show through Patreon Shop for or sell sailboats at SailboatsForSale.com Sail in New England / Canada with Sailing Resolution Get marine electrical help from Meridian Marine Electrial Shop LED navigation lights at Signal Mate