Anguilla has been our favorite island in the Eastern Caribbean for a long time. There’s a whole lotta’ nothin’ happening here; the people are open, easy going, friendly; and the white sand beaches are as sweet as sugar. Sailing in felt like a homecoming. Soon after we anchored in the port of Sandy Ground, we went ashore to clear in and even that was simple … no complicated forms, no charges, just “Enjoy your stay on Anguilla,” from the customs lady.

The first place we went was “The Delicate Bar,” a small, square cinder-block building on the road facing a salt pond. Years earlier Bruce had painted two murals on the outside for Belto and Duda, the aging West Indian proprietors. During the few days it took to complete paintings of the island’s most famous schooner, Warspite, and an underwater scene, “The Delicate Bar” became the place to be. It was hopping.

As we approached the now plain, white building, our hearts sank. There was no outward sign of business. We knew Duda had passed away after two fierce hurricanes whacked the area in the late 90s, but as we passed by, we slowed to look in the open door and there sat Belto behind the bar in his crooked captains chair. “Belto! How are you? It’s Bruce and Jan!”

“Fine, fine,” he said with a smile growing across his face. Belto is a tiny but wiry 89-year-old, with eyes as blue as the sky. He told us about his few ailments, which didn’t seem to be slowing him down much, we ordered two drinks and sat across the wooden bar from him, egging him on to recount his days long ago, sailing on more than half a dozen island cargo schooners. Bruce wrote down their names in a little notebook, with Belto making sure he got them right, as he worked to recall a lost piece of Anguilla’s history. “You got Betsy?” he asked as he looked at the paper. “What yuh got de? You got Industry? Alice? Izme?”

Later that day we decided to stroll the beach to check out the new establishments before returning to Woodwind. The first one was geared for hotel tourists, so we gave it a pass and moseyed further down to Elvis’ bar. Built out of one of the old island race boats, the bar itself is inside the boat and customers sit along the outsides of the hull or at one of the varnished wooden spool tables, all of it right on the sand. The crowd was an interesting mix of locals and visitors. Elvis and his partner, Brett, were busy in the middle. We sat for a while trying to get a feel for the place from the cross flow of conversations. A couple people pulled us in with a few questions and when they found out we’d sailed our boat from Washington State in the past nine months, we were in!

Elvis, a tall, thin West Indian, was a skilled bartender. Brett, an American newly transplanted from St. Croix, seemed to run the business end of things. They both gave the place a good feeling. At some point in the comfortable, casual, conversation, Brett mentioned to his friend, Susie, “Parrothead should be here soon.” He picked up a portable VHF radio and called, “Parrothead, Parrothead, Elvis.” With no answer, he put it down and I blurted, “Parrothead? Parrothead, the boat from St. Croix?”

“Yeah,” he answered. “They’re coming over for the concert. They should be here in 10 minutes.” I looked at Bruce. “Did you hear that? Parrothead is coming here!”

Last Halloween, as we motored out of the channel in San Diego, we looked over and saw a boat slowly passing us. On the stern, Parrothead, St. Croix was written, along with, of all things, a colorful parrot. We figured it was a charter boat on its way back to a busy Caribbean season. Two or three days later we heard Parrothead talking on the VHF. Like us, they were headed straight to Panama. A blow was coming, though, so they were going to take shelter on the Baja’s Turtle Bay to wait it out. “Sissies!” we said, pumping ourselves up, brave and tough, thinking we could handle any weather Mother Nature could dish out.

The days of November passed slowly on the Pacific. We’d often say, “I wonder where Parrothead is? Maybe we’ll transit the canal together,” and so on. Thanksgiving morning as we rounded the outlying points of land leading into Acapulco Harbor and approached the anchorage, we spotted three cruising boats. With the binoculars I checked them out. “You’re not going to believe this,” I said. “Parrothead is here. What a small world. I can’t wait to hear where he was for the hurricane.”

But we never had a chance to ask. We missed each other coming and going; they left the next morning in a hurry. We didn’t give up on them, though. They remained the gauge of our progress. When we finally got to Panama almost six weeks later than planned, we imagined they were already on charter in St. Croix.

Parrothead pulled into Sandy Ground after we’d returned to Woodwind. Once they had their anchor down, we called them on the radio, reminding them where we’d seen each other and asking them to stop and see us on their way in. When they came by, the captain turned off the outboard and asked, “Are you really from Gig Harbor?” He looked a bit confused, almost shocked.

“Yes,” I answered. “Do you know the place?”

“I was born and raised there,” he said.

I next asked, “Who are you?” because Gig Harbor is a town thick with Yugoslavian names. If his last name had “ich” at the end of it, we would know his family for sure. He brought his dinghy alongside Woodwind for introductions and explanations. Parrothead was built by his father about 12 miles from where we built Woodwind. Our boats had been at docks just one block apart for years. We told him about our episodic adventures since leaving San Diego. His trip, which ended in St. Croix in late December, was far more uneventful.

The next day at Elvis’ bar, we hung tight together, talking about our hometown, our Gig Harbor boats, the long voyage we’d had. The odd string that bound us together like pearls was yet another reminder of this small world we sail and walk on.

By Saturday morning the seven-mile, eel-shaped island swelled up like a perturbed puffer fish as over 4,000 parrotheads descended on it. Not boats, but crazed Jimmy Buffet fans who flew in, sailed in and ferried over from St. Marten; some may have even walked on water to come see the man who sings about the life they wish they had of sailing, singing and looking for a lost shaker of salt.

Arriving in Anguilla three days before the concert had given us a chance to watch the frenzy in the anchorage, normally a quiet place with assorted local boats, a dozen bareboats coming and going and an occasional cruising boat. Over 30 cruising boats arrived for the concert, flying pirate flags, their crews decked out in loud, tropical attire and Buffet-esqe T-shirts. Jimmy tunes blared through the fleet as the three-day party got underway. Each afternoon, the beach became a parking lot of inflatable dinghies, as crews and their guests went in to float between the half dozen bars on shore. The smell of barbequed ribs and chicken poured out of Johnno’s, Roy’s, Elvis’ and the other establishments, along with pulsing reggae and jazz.

The venue for the concert was at the Dune Preserve, a postcard-perfect property on Rendezvous Bay, owned by Anguillan reggae singer, Bankie Banks. Inside the gates of the Dune are an eclectic collection of small buildings, Swiss Family Robinson style, along with a stage and an upper deck area built for the big event. Gates opened at noon Saturday and security was tight. The concert was being filmed professionally for a video, so only still cameras were allowed inside.

Bruce and I captured two coveted spots in the shade, where we would wait two hours for the show to start. The place slowly filled with costumed revelers, some wearing parrot hats, others shark fin hats or homemade “I love Jimmy Buffet” hats. Half the people were in swimsuits or assorted alluring beach attire. It was peak people watching.

A helicopter full of cameras flew over repeatedly, igniting the fire of anticipation cooking the crowd. Around 3 p.m., with 1,000 people still lined on the beach waiting to get in, Bankie Banks took the stage to welcome the crowd to Anguilla and introduce “the man.” They went nuts. Jimmy Buffet and the Coral Reefer Band came out and got right to work. They didn’t disappoint, playing dozens of their hits.

Some of those songs were about shared memories we had in St. Barts in the late 1970s, when we, Jimmy and dozens of wooden, classic and character boats called the little island home. Bruce painted the first Cheeseburger in Paradise sign there for Fast Eddie at Le Select, along with one that said, “Cheeseburg, Cheeseburg.” The latter, of course, just never made it into a song!

The heat of the day was intense. People streamed back and forth to the beach to jump in and cool off. Some braved a 45-minute line to buy drinks, soggy burgers, dogs and, of course, T-shirts. Two and a half hours after it began, the concert came to an end. Jimmy thanked the crowd and encouraged them to party on, as if they hadn’t already thought of it.

Back at Sandy Ground, the bars and restaurants were overflowing with full-on friendly crowds. It was as if the concert had been the prelude to the real round of parties. We met people who had come from Kansas, California, Wisconsin and every state in between, simply to change their latitude, their attitude and get a dose of island life on sleepy little Anguilla. They played and partied till dawn. We haven’t been to the island’s airport yet, but we’re sure there must be a sign at the departure terminal that reads, “What happens in Anguilla, stays in Anguilla!”