I sailed into Key West the first time aboard a 26’ sloop in May of 1975. My then girlfriend, Chris Vogt, had bought the sailboat, The Original, 18 months earlier and we had cruised down from St Pete via Sarasota and Fort Myers Beach. At each stop we would work odd jobs to save enough money to finance the next leg. I’d work in boat yards, getting ‘hands-on’ training in the art and science of marine outfitting while Chris would waitress.
We’d wintered over in Fort Myers Beach, a laid-back community on Estero Island across the Caloosahatchee estuary from Sanibel Island. The blue-rinse set, hippies and good ‘ol boys. With the arrival of spring it was time to move on. We planned to sail through the Everglades via Whitewater Bay to Flamingo and then hop the Keys out to the Dry Tortugas and Ft Jefferson.
Mike Roselle thumbed down from Kentucky to join the crew. He was flat broke but he’d just seen the Dead in Louisville.
The three of us sailed out of Estero Pass on the 2 April and set our course due south, past Marco Island, for the Shark River. We could anchor off beautiful deserted beaches to swim during the day and sail offshore at night. Surfed over the bar into Ponce de Leon Bay and then up the Shark River estuary to Whitewater Bay.
Me being me, I kept an official log of the voyage, recording winds, headings and events. Not a travel journal, just the key metrics.
Tacked back and forth thru the Bay, gorgeous swamp and mangrove channels. Anchored away from the shore to avoid the skeeters at night. Sailed to Oyster Bay and then motored along the Wilderness Waterway into Flamingo, headquarters of Everglades National Park.
Met a young lady, Cheryl, who had just quit her job with the National Park Service in Flamingo. She was planning to drive her van up to Jackson WY to open a Western Art gallery. We invited her to come along.
Leisurely sail along the Keys past Bahia Honda and the Overseas Highway. Passed Key West at night, stayed well south of the reefs. Checked our position at the Rebecca Shoal Lighthouse and steered west nor’ west.
The wind picked up that night and we literally surfed into the sheltered anchorage off Ft Jefferson. For the next few days we explored the well-preserved fort and dove on the amazing reefs. Even found a coral-encrusted cannonball.
At the time, smuggling was big business. We were boarded regularly by the Coast Guard and Marine Patrol. The Coast Guard were pros, very polite. But the Marine Patrol guys, not so much. They could be, ah, overzealous, in their shakedowns as they searched the boat. It would take hours to clean up after them. We were always very discrete.
Sailed out of Loggerhead Key on the 28 April, Key West bound. The Gulf Stream pushed us east and the wind blew us west. A very bumpy ride. 18 hours to sail the 19 miles to Rebecca Shoals. Anchored off.
Three more days of long tacks brought us close enough to motor in. Anchored off Mallory Square on Key West on 2 May after sailing 150 miles on 65 hours. Whew.
After a month’s cruising – 408 miles exactly from Ft Myers Beach – we were almost broke. Found an open berth at the Key West Yacht Club and settled in. Cheryl was still keen to drive up to Wyoming so she and Mike said adios. I picked up a boatbuilding gig at Steadman’s Boatyard on Stock Island and Chris worked as a dancer.
It’s already unbearably hot and humid in Key West by May. 90 degrees at 8am, 98 percent humidity. Sweating is a way of life. But in the evening, Key West is a tropical paradise. Frangipani, jasmine and Latin rhythms scent the air. People move slowly, drinking in the atmosphere. And a great place for a bike. I had an old one-speed and cruised all over town late at night. Dead flat, not much traffic.
We moved into the upper floor of an old Conch house on Caroline St, just off Simonton. Big open veranda, louvred windows, high ceilings. We’d even catch some sea breezes at night.
Key West was just starting to gentrify. Wealthy outsiders were swooping in and buying up all these beautiful old wood-frame houses. Some got renovated, others got bowled. The traditional Cuban/Conch/Bohemian locals were getting squeezed. Younger families couldn’t afford to live in their own hometown. It’s a story we’d hear over and over again…
Sailed the ‘Original’ up to Lauderdale that winter and hauled her out at the River Bend Marina. Rented a cute little cottage off Sunrise Blvd. Got a job as a taxi driver, Chris a cocktail waitress. Days at the beach, nights cruising from dinner club to disco in my cab. Fun for a while, but no future. Chris and I drifted apart.
In April 1975 my brother called. My dad needed help around the house – he’d hurt his back. Could I come up for the summer?
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