A Parrothead's Journeys HOME

Adventures and encounters during a 1989 surf road trip now dubbed
"A Surfer Looks at 30".

This photo was taken Memorial Day weekend, 1989, at the Margaritaville Cafe, Duval Street, Key West, Florida, during the tail end of a 2 week pre-mid-life crisis surf journey that went down the east coast as I traveled from Maryland to Key West and back. I turned 30 in May of 1989, and it seemed as good an excuse as any to go "walkabout". See the story below.

I was able to get the autograph on the mat around the photo several year later at a booksigning Jimmy did in the Washington D.C. area for "Where Is Joe Merchant?" (I took the photo with me, matted and framed ...... just in case), but that's another story.

May 1989

Feeling like an aging surfer (ok, that's a stretch, but I did turn 30 in May 1989), I took a 2+ week road trip down the east coast, stopping in Virginia Beach, the Carolina Outer Banks, Daytona Beach, Florida for a little mind clearing, soul searching surf journey. Ok, again that's a stretch - basically I was goofing off like I hadn't been able to do since high school. My then girlfriend and later bride(1) took it all in stride, more or less.

Drive south far enough and you run out of road down in Key West well past A-1-A. The other cool part of this particular trip, I was able to take my new, at the time, convertable first generation Toyota 4Runner with the hard top removed.(2) "Rag Top Days" all the way down the coast..

This wasn't my first trip to the keys, maybe about my 6th or 7th, but was the first time I had the luxory of taking about 2+ weeks to do so with no particular agenda other than finding the best surfing and waves I could. Fast forward to a lazy and hot afternoon, sitting on a bar stool at the Margaritaville Cafe chatting with the bartender and downing several beers. For a Memorial Day weekend, it wasn't really all that crowded. Maybe 20 or so people scattered around. About 3 of us at the bar, a few couples at the tables, and a group of 4 people over in the corner booth table at the end of the bar near the stage.

I'd been in town about 3 days, but this was the first time I had seen this bartender. Turns out his name was also Bob. Of course I had to ask the tourist question once again, "So Bob, how often does Jimmy actually come in here?". This time, instead of the usual "He was here just last month" response, Bob the bartender nods his head in the direction of the group in the corner booth table over by the stage. Danged if it wasn't Jimmy himself with a briefcase opened and talking to 3 business types who clearly weren't locals, maybe record executives or something or other, I dunno

Well now I don't know just exactly what to do or say. Obviously I don't want to blow this opportunity, but how to ....? I mean what should I do? Should I .... ? I just don't know.

Bob the bartender takes all this in and helps me out. "You don't want to bother him now. Wait until he stands to leave and have a pen and something ready to be signed. He's usually pretty good about it".

Well I've got no pen, so I borrow a pencil of all things from behind the bar and the only paper I can find is a Margaritaville Cafe menu. Now I wait. It didn't take long, maybe 15-20 minutes and Jimmy and his table companions stand and begin shaking hands and obviously their meeting was ending. Believe it or not, of the 20 or so people in there, apparently only myself and a newlywed type young couple know that Jimmy's there and approach him.

"Whoa", Jimmy says feigning some good natured surprise as he stood and the newlywed couple and I converged on him with our pens (pencil) and paper in hand. He was gracious and signed the menu for me (in pencil) (3)and also signed something for the young couple. Now then, we (the newlywed couple and I) each had cameras and one of us asked if he minded if we took a picture. Jimmy said something to the nature of "I tell you what, I've got a little more business I need to take care of upstairs" (there's an office on the 2nd floor above the stage), "but when I'm done I'll meet you out front of the Cafe in 5 - 10 minutes and I'd be happy to oblige" (or something like that, I was still a bit flustered by this opportunity). And so off Jimmy went upstairs.

Well the couple and I beeline for the sidewalk in front of the Cafe and begin excitingly exchanging names and start showing each other how to use one another's cameras, and basically rejoicing over our good fortune. We agreed to take 2 pictures each if we had time, to make sure we got a good one. Now the 5 - 10 minutes Jimmy spoke of went by. Then 15 minutes ... 20 minutes ... now at least a half hour has passed. "Son of a .... !", I'm thinking, "He's either plum forgot about us or else skipped out the back way."

Well just as I'm about to lose hope, sure enough here comes Jimmy walking right through the not so crowded Cafe, and this part ...... I kid you not ...... happened next. He walks right behind another couple who were looking a a picture of Jimmy performing on the Margaritaville Cafe stage that was framed and hanging on the wall near the front door by the bar. The woman from this other couple is pointing to the picture and telling her husband "See honey, he comes in here and performs sometimes" ... this while Jimmy himself is walking right past them!

Jimmy exited the Cafe and met us right out front on the Duval Street sidewalk and shakes hands with us. He couldn't have been more pleasant and even spent a few minutes chatting. "Where y'all from? Maryland? Merriweather Post Pavilion, the Chesapeake Bay .... know it well". I'm paraphrasing a lot. To be honest I really don't remember much of the conversation, but I distinctly remember being really pleasantly surprised that he genuinely took a few minutes to talk.

Well he posed for the pictures, shook our hands again, wished us well and turned to walk down south down Duval Steet with briefcase in hand. Then a left turn at the end of the block probably heading towards what I later learned was another office just around the corner and up on the 2nd floor behind the Cafe.

That was it. Short encounter but still so very cool. I immediately went to a 1 hour photo place a couple of blocks away and got the pictures developed right away. I neglected to get the other couple's address, I wish I had so we could have exchange stories later but I didn't. I also wanted to take the developed photo over to 2nd couple to show the husband that his wife was right, Jimmy does come in here occasionally and you missed him by 3 feet! They were gone however by the time I returned with my developed photos.

That's my story and I'm sticking to it.

(1) My wife today claims that I take better care of my pictures with Jimmy Buffett than I do of our wedding photos.
(2) Man, I loved that truck so much I ended up driving it 16 more years and over 265,000 miles before selling it sadly in 2005.
(3) See this link for the pencil scrawled autographed Margaritaville Cafe menu.