If you’re lucky, Dick Franyo might sing you a Jimmy Buffett song.

He owns Boatyard Bar & Grill, a popular restaurant in Annapolis. He opened it in the Eastport neighborhood after moving here in the early ‘90s and then retiring from a career as an investment banker. Together, they have become well-known members of the community.

And Franyo is a fan of the late singer-songwriter, one of many in Annapolis. He had “three good meals” with Buffett, and keeps photos of them sailing together on the walls of his restaurant and his phone.

“What I love is that he was a poet,” he said. “If you listen to his early stuff, he was a poet.”

He knows the lyrics to “Someday I Will” well enough to sing them unprompted during a phone call about Buffett and his lingering influence on Annapolis. He used to sing it for his kids as a reminder that anything is possible.

I see a white sail skipping ‘cross a blue bay

And I say someday I will

I see a young man strumming on a green guitar

And I say someday I will

Jimmy Buffett, “Someday I Will”

Buffett, who died in September at 76 of skin cancer, wrote hundreds of songs in his career. Most people, whether they like his three-quarter-time rhythms or not, can name a few. Yet it is more than that.

You hear Buffett’s tropical-rock sound around the city, in marinas or wherever boaters raft up for a summer afternoon. Maybe it’s the laidback vibe Annapolis wears so casually. No socks, no ties but plenty of boat shoes. Maybe too many margaritas.

Whatever it is, there’s a relationship. Understanding it is a chance to know Annapolis through the songs of a man who never called it home, but often called to visit.

If you’re lucky, you can hear some of them at Annapolis Summer Garden Theatre through Saturday.

The community theater troupe is wrapping up a sold-out, monthlong run of “Escape to Margaritaville,” the jukebox musical based on his songs. It didn’t last long on Broadway, but it’s found a receptive audience in its converted blacksmith’s shop a few steps from the water.

From the very start, director Melissa Huston knew this show would be something different.

“I wanted to build a Buffett world that was more authentic,” she said. “And more true to Jimmy’s roots since it’s Annapolis and we have a lot of people here that have stories.”

There are Easter eggs hidden in the set for Margaritaville — the clock is set to 5 o’clock somewhere, and that volcano is gonna blow. The real surprise may be Tom Cagle. It’s the 52nd set he’s helped build for the company.

Beneath a wide-open parrot print shirt from Key West, his bare chest is decorated with a seashell necklace. The 72-year-old hammered and wired his love for Buffett’s music into the collection of reused flats and brightly colored backdrops for the show.

“Going through the process of building it and knowing that you’re doing it for a person that’s no longer here, it’s, it’s like adding to the legacy of his life,” Cagle said. “It’s a tribute, a tribute to a friend.”

His favorite song remains “Come Monday,” Buffett’s first hit. It’s about loneliness and longing for home, an understandable choice for a fan whose wife died several years ago.

Come Monday, it’ll be alright

Come Monday, I’ll be holdin’ you tight

I spent four lonely days in a brown L.A. haze

And I just want you back by my side

Jimmy Buffett, “Come Monday”

Here’s the story Cagle tells. He says he drove 21 hours from Baltimore to catch a friend who was opening for Buffett in Key West.

“After the concert, I went up on stage and said, ‘Hey, I really appreciated it.’”

His friend asked if he wanted to hang around for dinner, and soon the table of 26 included Buffett.

“I got a 21-hour drive home. But sure, I’m gonna hang around!”

There are lots of people in Annapolis who met the singer and more who attended his concerts and feel like they met him.

Jimmy Cantler, the former waterman, got years of stage shoutouts for his namesake restaurant near Annapolis when Buffett’s concerts came to Maryland. The singer was a regular customer for a while.

A friend of mine wrote about the relationship, and discovered that Cantler shared his favorite Buffett song, “A Pirate Looks at 40.”

It’s about dreams you haven’t achieved, and Rob wouldn’t live to see any of his books published.

Yes, I am a pirate, 200 years too late

The cannons don’t thunder, there’s nothin’ to plunder

I’m an over-40 victim of fate

Arriving too late, arriving too late

Jimmy Buffett, “A Pirate Looks at 40.”

Maybe the connection to Annapolis is in the way Buffett parlayed his carefree image into a business empire worth billions, with restaurants and resorts, books and merchandise, and even a short-lived CBD and cannabis brand, Coral Reefer™.

Annapolis is an expensive place to live that attracts people with the money. Maybe part of the appeal is an appreciation of success, even the kind that doesn’t make you rich.

“He was someone who said you have to get off your ass,” Franyo said.

If you’re lucky, you might get to talk with retired astronaut Ken Reightler.

More than just about anyone, his Buffett story brings together a lot of the ties between the singer and the city.

Reightler was in charge of communications with space shuttle astronauts at NASA, and later with the International Space Station. On one mission, an astronaut asked for Buffett’s “Gravity Storm” as wake-up music.

The mission included gravity experiments. But the song is about how life comes with the unexpected, and sometimes it’s a storm. Buffett found out and called to suggest playing something else.

“They said Mr. Buffett’s on the phone, and I said what does Warren Buffett want?” Reightler said, saying he thought the billionaire investor had called.

Oh, watch out for that gravity storm

It don’t give no warning signs

Oh, watch out for that gravity storm

Oh, oh

Jimmy Buffett, “Gravity Storm”

The call didn’t change the song, but it led to a tour of NASA in Houston for Buffett and an unexpected friendship for the retired Navy captain. There were impromptu concerts for space-borne audiences, and one for the shuttle program staff when it was shut down.

“We discovered we had a lot in common. We were both sons of a son of a sailor.”

When Reightler came to teach at the Naval Academy, Buffett followed in his wake. There were concerts for midshipmen and introductions to Franyo. He came here in 2016 to sail on a replica of the original America’s Cup champion, America, and to meet the local sailors sailing in the competition.

Buffett’s last trip here came in 2020. He got a tour of the Thomas Point lighthouse from Dave Gendell, author of a book on the historic beacon near Annapolis.

Buffett’s teal 42-foot motor yacht, Last Mango, tied up to the Chesapeake Bay landmark. He recorded a few songs for a project intended as a COVID concert but that was never released. More were recorded aboard his 50-foot sailboat, Drifter, in the Severn River and Whitehall Bay.

Some of the videos showed up in his last performance at Merriweather Post Pavilion in 2022, his home Maryland stage after 48 concerts over 45 years.

Maybe Buffett’s appeal in Annapolis is about his talent as a musician, having sold 20 million copies of his songs, earned a couple of Grammys and planted himself firmly in the book of dockside bar standards.

Members of the Coral Reefers, Buffett’s band, usually turn up at the Annapolis Maritime Museum’s end-of-summer fundraiser, the Boatyard Beach Bash. They’ll be there again in September.

“We have five of Jimmy’s Coral Reefer band come and headline it,” Franyo wrote in a text after we got off the phone. “Amazing musicians.”

But maybe it’s just the connections with people that explain the feeling for Buffett in Annapolis, whether through a friendship, a chance meeting or just the right song at the right moment.

Everybody loves “Cheeseburger in Paradise.” Who hasn’t shouted “Salt, Salt” after hearing someone sing “Wastin’ away again in Margaritaville, Searchin’ for my lost shaker of salt?”

Maybe someday Buffett’s connection to Annapolis will fade. Fans age. Tastes change.

If you’re lucky, you’ll get to hear “Bubbles Up.” It’s a song Buffett had arranged to have released shortly after his death.

It’s Reightler’s new favorite, a spiritual riff based on a safety technique for the day you crash into the water and lose your way.

And a promise of an afterlife, even if it’s just playing somewhere in Annapolis.

Bubbles up

They will point you towards home

No matter how deep or how far you roam

They will show you the surface, the plot and the purpose

So, when the journey gets long

Just know that you are loved

There is light up above

And the joy is always enough

Bubbles up

Jimmy Buffett, “Bubbles Up”

This column has been updated to correct Tom Cagle's marital history. His wife died several years ago.