When President Donald Trump came to Little Havana to announce revisions to the United States policy toward Cuba travel, he never mentioned Key West by name. But the Southernmost City was in the speech.
Trump excoriated Cuba's revolutionary regime, capping it with the fact that the island "once tried to host enemy nuclear weapons 90 miles from our shores."
That reference to the 1962 Cuban Missile Crisiswas also a reference to Key West, famously closer to Havana than it is to Miami. The two islands were linked in commerce and culture until the Cuban embargo slammed the door on open exchange in 1960.
But that doesn't mean travel across the Florida Straits stopped. Cuban refugees continued to make their way across, with the numbers swelling past 100,000 during the 1980 Mariel boatlift, and then into the tens of thousands during the rafter crisis of 1994. After that, the wet foot, dry foot policy continued to give refugees an incentive to cross the Straits, in homemade boats or smuggled in powerboats.
And on the Key West end, boaters sometimes made their way across.
"There's a 400-year-old city just a few miles south of us. Most everyone that I know that's been in Key West long enough starts to cast an eye down to the south," said George Bellenger, who runs an eco-tour business in Key West.
Bellenger first made the crossing 20 years ago after he acquired a Hobie Cat — a 16-foot catamaran with no engine — for $100. He fixed it up and got a friend to make the trip with him.
"We had duct tape, we had string," he said. "We had something called a GPS but we weren't quite sure how that worked — we were going to figure that out once we got out on the water."
Miraculously, they made it across — though they missed their target by about 20 miles.
"After about four hours of paddling along the Cuban coast, we pulled in to [Marina] Hemingway around midnight," Bellenger said. "They were scratching their heads. They tore our stuff apart pretty good."
More miraculously, Bellenger and his friend made it back to Key West, despite a hurricane whirling around in the Gulf of Mexico.
Read more: When Key West Was Cuban
In the last three years, since former President Barack Obama re-established diplomatic ties with Cuba, Bellenger has crossed the Straits again, this time as an organizer of the Havana Cat Challenge. Hobie Cats set off from Key West. Those that make it to Cuba intact race against Cuban sailors, some of them Olympians.
Hobie cat diplomacy
Bellenger says the Cubans are still scratching their heads at the Americans.
"Most people have heard of gunboat diplomacy. When we show up on our Hobie Cats, people can't help but smile," he said. "So we call that Hobie Cat diplomacy."
David Dlugitch, who owns a conciege website called Key West Travel Guide, was along on this year's Havana Cat Challenge. But on a 70-foot sailboat, one of the support boats that travels with the group in case something goes wrong (and something usually does).
Dlugitch first sailed to Cuba more than 15 years ago.
"This time, when I went down, there was really a sea change," he said. "You suddenly saw young people that were willing to speak critically about their situation."
He credits that to the entrepreneurial economy supported by individual American travelers over the last couple of years — the same people who will now likely be banned from going to Cuba. The new rules are expected to crack down on the "people-to-people" travel allowed under the Obama administration, with Americans required to travel in groups with a licensed group leader.
"There was more creativity, there was more ideas and businesses," Dlugitch said. "And you could see that people were starting to gain independence from the state, in a way."
'Worrisome for people that believe in freedom of the seas'
Dlugitch is also concerned about what the new rules may mean for mariners.
"What's going to happen with individual boats — that's something that's near and dear to people in Key West," he said. But the new rules may limit Americans from spending money at facilities controlled by Cuba's military, or the military's tourism subsidiary.
"Will they still allow boats to pay dockage, even if they're in a regatta?" Dlugitch said. "That's yet to be seen and it's worrisome for people that believe in freedom of the seas."
Nance Frank was born and raised in Key West, and grew up speaking Spanish and taking classes at the historic San Carlos Institute. She first visited Cuba 25 years ago, by accident — she was sailing back to Key West from the Dry Tortugas.
"The boat had problems," she said. "Any port in a storm is the maritime rule."
Now she represents Cuban artists at her art gallery in Key West, Gallery on Greene, and travels back and forth regularly.
She says she's also seen big changes since more Americans have traveled to Cuba individually.
"Entrepreneurialism, which is what the great American dream is all about, was at an all-time high. And now that's going to change," she said.
She says artists who haven't made it big enough to get American representation like her will lose access to potential buyers.
"They will lose revenue, just like the Airbnbs, the private homes and the restaurants," she said.
For now, Key Westers are like everyone else, waiting to see the details in the new rules and how their travels across the Straits may be affected. Bellenger says he doesn't know yet whether there will be a fourth Havana Cat Challenge next year.
"Every year as soon as I make sure that all hands are safe, I say, 'Never again.' Every year, 'Never again,'" Bellenger said. "Then after a week, it's like , 'Well, maybe.' Now it's been a month and because of these rule changes there might be an extra challenge of doing it. So we're looking at it as a definite maybe."
