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Jimmy Boylan was scheduled to depart Thursday, sailing his sloop “The Speakeasy” to Cuba – but with 25-knot winds off of Marco Island, and thunderstorms in Key West, the decision to wait it out in safe harbor was “a no-brainer,” he said.

“The weather’s not getting any better, and the Cubs are playing. The boat’s an old bird, and hey, we’re old birds too,” he said from his slip at Anglers Cove. The weather gods finally shone on them, and the Speakeasy got underway around sunset on Sunday for an overnight sail south. Boylan’s plan was to make a quick stop in Key West – “just a bump and run” – to pick up one more crew member, and then head out across the Gulfstream to Marina Hemingway in Cuba.

Boylan, along with a boat named Speakeasy, a 1985 Endeavor sloop with 33 ft. overall (LOA) and 27 ft., 6 in. at the waterline, (LWL) is part owner of the Speakeasy restaurant on Marco. One might have guessed this, aboard his boat, where everything from the name on the transom to towels, napkins, crew shirts, and drink holders is emblazoned with the Speakeasy logo, with a Tommy gun-packing flapper and the “Y” turned into a Martini glass.

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Crew members include Bobby Nash, and John Gantz, a Coast Guard-certified 100-ton captain who is a veteran of two trans-Atlantic Ocean crossings. Nash, whose day job is tending bar at Quinn’ on the Beach, brings that skillset with him – “I can make a lot of drinks fast,” he said – but also is proficient in the ancient and perhaps dying art of celestial navigation. He will be taking sightings with his sextant, although the Speakeasy is also equipped with modern GPS technology, although not radar. The crew joining in Key West has even more experience, said Boylan. The boat is literally a registered antique, he said, qualifying by being over 30 years old.

In Cuba, the crew is hoping to scuba dive at some of the relatively unspoiled dive sites scattered around the island, and on land, to soak up the culture of this Caribbean island that for over 60 years, has been so close but off limits to visits from the U.S.

“We want to see Cuba before it gets too big, too built-up,” said Gantz, who has visited before. “When I was there, it looked like Hemingway might come out at any moment.” Tunes on the stereo for the cruise down are expected to be heavy on the salsa, featuring the Buena Vista Social Club.

One planned dive area is in the Bay of Pigs, which Americans of a certain age will remember as the site of the U.S.-sponsored invasion against the Castro government in 1961. But now, friendly relations are restored. The voyagers have cleared their trip with U.S. Customs and the Coast Guard, and must merely notify U.S. authorities by phone when they cross from one country to the other.

“We’re on the honor system,” said Boylan. “In Cuba, the government will take care of all our issues when we get there. We can get our visas on the spot.” He had his Cuban courtesy flag ready to bend and fly from the yardarm, as well as a yellow quarantine flag. While not expecting difficulty, Boylan planned to strap his inflatable dinghy over the cabin, rather than having it sit in its usual place on the davits behind the transom, and he has a “ditch bag” ready to go, with emergency beacon, handheld VHF radio and GPS, extra batteries and jugs of water.

One member of the crew on Thursday, Gantz’s girlfriend Carol Cermak, is not making the Cuba leg of the trip.

“It’s not a girls’ trip,” she said. “This is going to be a fraternity boys’ trip, of the worst kind,” which prompted some pushback from the male crew members on board. “Of course, they are older now,” she conceded.

“When this boat was built – 1985 – we would’ve rocked it,” said Gantz. They were dependent on Cermak for provisioning, as she prepared food for the trip over, so the men would not have to spend time in the galley. She is hoping to rendezvous in Key West and be part of the last, homeward leg of the trip.

While Cuba travel has opened up in the last couple years, bookings and flights are down, as American tourists have found amenities are not always up to their wishes, and there is uncertainty about the stance of the Trump administration to the loosening of restrictions. We will check back in with the crew of the Speakeasy on their return, to see how their experiment in personal, sea-going diplomacy fares.

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