In late December 2024, Key West lost one of its most colorful and legendary characters: Captain Finbar Gittelman, who will never be forgotten on the island that was his home port for some 50 years. He lives on through the schooner Wolf that he built and captained, and through the irreverent independence of the Conch Republic he helped shape.
The quintessential seafarer, called simply “Finbar” by practically everyone who knew him, grew up on Miami Beach. He first came to Key West as a child with his parents to board the then-operating ferry to Havana, Cuba to visit relatives. He made the island his permanent home in 1973.
“When I sailed into Key West Harbor anchorage, dropped anchor and looked around, I knew I was home,” he said in 2018.
While he relished the island’s seafaring atmosphere and freewheeling way of life in the 1970s, he was surprised at the lack of passenger sailboats. In 1980, Gittelman built the 33-foot sloop High Tide, designed for day sailing and trips to the reef.
In 1982, along with master builder Willis Ray, he began constructing the ship that would become his lifelong passion and frequent liveaboard home: the 74-foot, gaff-rigged topsail schooner Wolf.
“I’ve always loved traditional ships,” he said years later. “To me, the old ways are sometimes the best ways.”
Patterned after the 19th-century blockade runners that once plied the Florida Straits, the Wolf was ultimately designated the flagship of both the Conch Republic — the Keys’ offbeat alter ego — and the city of Key West. The venerable vessel was headquartered in Key West and neighboring Stock Island for some four decades, operating as a passenger boat that offered specialty day sails, private charters and even extended voyages.
Rising quickly through the ranks of the colorful Conch Republic Military Forces, Gittelman eventually earned the titles of admiral, first sea lord and supreme commander. For decades he and the Wolf led the republic to victory in its yearly “sea battle” against the U.S. Coast Guard and federal government — a highlight of the annual Conch Republic Independence Celebration that commemorates the “nation’s” 1982 birth. That was the Keys’ symbolic secession from the United States in opposition to the federal blockade at the top of the Keys that aimed to curb drug smuggling, but instead crippled tourism.
He also portrayed a pirate king during Key West’s long-running Pirates in Paradise festival, a rollicking revel for buccaneers and wenches that was created and coordinated by his wife and soulmate, Julie McEnroe.
But there was far more to Finbar than the personas he assumed with devil-may-care enthusiasm. In 1980 he and three shipmates survived a deadly Caribbean hurricane at sea, spending harrowing days in a tiny life raft after their vessel sank in the Category 5 storm.
Perhaps as a result of that experience, over the years Finbar and first mate McEnroe sailed the Wolf on numerous humanitarian missions of mercy in the Caribbean, delivering cargoes of food and relief supplies to areas devastated by hurricanes, earthquakes and other natural disasters.
The couple also poured their hearts into teaching seafaring skills and traditions to young mariners — a primary focus of Finbar’s life.
“I love teaching young sailors the ancient art of sail,” he said several years ago. “I want to pass on what I know and try to show them the spirit of the sea.”
Finbar’s life provided him with fodder for a wealth of stories — and as his friends can attest, he told them masterfully. Some of his most distinctive tales were captured in “The Old Man and the Sea: Return to Cuba,” a documentary released in 2018 by Matt Dean Films, that explored the captain’s seafaring spirit and first journey to Havana since his childhood.
But no matter where he sailed, Finbar’s affection for his island home never wavered.
“I’ve been to many ports and none of them have the way of life I love here,” he said in 2018. “Key West is one of the places in the world where you can be yourself, and this is where I belong.”
Finbar’s ‘Crossing the Bar’ memorial set for April 23
Friends and fans of Capt. Finbar Gittelman, the schooner Wolf and the Conch Republic are invited to celebrate the captain’s life and legacy at a memorial ceremony and dinner on Wednesday, April 23 from 5 to 9 p.m. at the Sunset Pier at Ocean Key Resort & Spa. Before that, the Tropic Cinema will host a free screening of “The Old Man and the Sea: Return to Cuba” documentary about Gittelman at 1 p.m.
Named for the traditional term for a sailor’s passing, “Crossing the Bar” refers to the journey from a sheltered harbor to open, unpredictable seas. The Gittelman gathering is part of the 2025 Conch Republic Independence Celebration. Admission to the ceremony is free, but tickets for the seated dinner are $45 per person and reservations are suggested. Visit conchrepublic.com.
A portion of the evening’s proceeds benefits the Schooner Wolf Restoration Fund, created to support much-needed renovation and repairs to Gittelman’s beloved tall ship — and preserve its purpose as a “classroom” where new generations can learn the art and traditions of sailing.
