For anyone sailing the south coast of Cuba, one inevitable stop is the marina at Cayo Largo in the Canarreos Archipelago. And the first and most unforgettable person they are likely to meet there is Pire, the charming and well-connected harbormaster, or “captain of the port.”

Cayo Largo del Sur has one of the few up-to-date and fairly well-equipped marinas to be found anywhere on Cuba’s south coast. For boaters it’s the gateway to some of the nation’s top beach and diving destinations. Pire (pronounced “Piri”), has been its harbormaster for almost three decades and typically meets all visiting sailors as they tie up at the modern floating dock. More formally known as Juan Cid, he is legendary among those who do.

Short and wiry, shrewd and funny, always quick with a smile, he greets most of the crews in their own language. He speaks five fluently: English, Russian, Italian, French and Portuguese, in addition to his native Spanish. Pire is a master at smoothing and speeding the clearance process that foreign sailors have to go through when they arrive. In our case he hopped aboard each boat with the Guarda Frontera officers to wrap up the paperwork quickly. He also serves as entertainment director, helping to line up a day’s activities. He was delighted to host our large group of Americans.

Cayo Largo is a beautiful (if somewhat incongruous) communist-run Shangri-La for the wealthy, seemingly immune from scarcities on the main island more than 30 miles to the north. It was the first resort to be developed (in 1982) by the Castro government exclusively for foreign tourists, mostly Europeans and Canadians who arrive by plane on chartered todo incluido (all-inclusive) package tours.

Other facilities have been built elsewhere in Cuba and have become a significant source of desperately needed foreign revenue, but this was the first government-owned tourist preserve. Visitors enjoy the comfort of several luxurious hotels stretching along more than 12 miles of stunning Caribbean beaches. Fishing and dive boats are available (30 dive sites are nearby), along with kayaks, kite surfers and other beach toys. Special day trips with private lunches can be arranged to idyllic nearby sandy beaches, such as Playa Sirena, Cayo Piedra and (the one we chose) Cayo Rico — all with blazing white sand, swaying palm trees, iguanas and vibrant turquoise waters.

“I came here to Cayo Largo in 1989, 27 years ago, and to work here was a privilege. This was the most exclusive place in Cuba, the first key developed for tourism in Cuba,” Pire says. “There are many others now, but we were the first. Cayo Largo was a pioneer in tourism in Cuba.”

The marina has 95 slips with reliable electricity at the docks, a small chandlery and a remarkably well-supplied commissary. A little village has a medical clinic, post office and a bank (no credit accepted, but that is likely to change). Boats entering the country here will be inspected by customs, immigration, agriculture and health officials, but coastal cruisers (as we were) need only present the Guarda officers with their passports and dispacho from the previous port.

Both Pire and his small office behind the marina’s docks reflect the big presence this small nation has had in the world. On the table across from his desk sits a Navy officer’s hat, bearing the red hammer and sickle from the Soviet Union; sitting on top of it is a deckhand’s cap from its modern successor, the Russian navy. Circling the entire top of his office around the ceiling are dozens of courtesy flags from all over the world, given to him by cruising sailors who have tied up at Cayo Largo.

But his prize possession, both sharing the same stand on his desk, are the Stars and Stripes and Cuba’s somewhat similar red-white-and-blue ensign. The American flag had been given to him as a token of friendship 20 years ago by a passing U.S. sailor, but he had to hide it because of the political conflict then raging between the U.S. and Cuban governments.

“Because of the B.S. going on between Cuba and the U.S., we couldn’t display the American flag anywhere, so I hid it in my house. But on Dec. 15, 2015, when [President] Obama and Raul [Castro] announced the new policy, I ran to my room, took out my American flag, and I put it here on my desk with the Cuban flag. I immediately uploaded the photo to Facebook, congratulating the U.S. and Cuba on re-establishing contact,” Pire says. “These flags represent a lot: the end of an era, all we share, the love between the two countries, a better future. There isn’t any money in the world to buy these flags from me.”

Pire’s passion for Cuba and America also reflects the deep complexity of relations between the two countries. As a young man in the 1980s he was a translator with Cuban military forces fighting in Angola and Ethiopia for leftist governments there (opposed by the United States). In 1995, during a Class 1 powerboat race in Havana, he was personal translator to Fidel Castro — “he’s such a big personality” — and got to ride with el presidente in Castro’s Mercedes limousine. Pire is proud of his service to his country, of Cuba’s renowned public education and public health systems, and of its hard-won independence.

“Cuba has proven to the world it doesn’t matter how big or how small you are, you can resist. Fidel and Cuba have proven over 50 years they can prevail against a nonsense embargo,” he says. “There have been 11 [U.S.] presidents trying to defeat the Cuban revolution, and at the end of the day Cuba came out with a victory.

Among other Cubans (and Americans) I have spoken with, where that détente goes from here is anyone’s guess — although it seems likely to be good for business on Cayo Largo. “What comes next? I don’t know. I hope the changes are for the good for both sides,” Pire says. “The future is possible.” He describes President Obama’s new policy of détente as a “victory of the American people as well — there have never been any bitter feelings between the Cuban and American people.”