Yet another unconventional destination for this year’s annual March trip. Let me put it this way, if you can find a friend when your three years old, cultivate that relationship over fifty plus years, and then wait for that friend to make a bold life choice to move with his wife and two dogs to Key West, Florida, I highly recommend it.

And when that friend’s wife is the one who suggests you all descend on their place and volunteers to make herself scarce so you can have your “guy time,” you stop and understand just how sacred these friendships are.  

Ben and Susan (and Viper and Vulcan) have been living in Key West for a little less than a year, so when that invitation came through the group chat it didn’t take long for us to agree – Key West it was!

I flew into Key West airport from Louisville, via Atlanta, about mid-day Thursday and Mark was due in a few minutes after me, so Ben picked me up and we sat at the airport for a bit. Ezra had arrived earlier and was either napping or just hanging out at Ben’s place. It was beautiful and hot and Ben’s soft top Jeep made it even better as we sat and caught up while waiting for Mark.

We got to Ben’s after a quick stop at the liquor store, settled in, and Mark surprised us with awesome “Mensch Madness” t-shirts. It’s the familiar NCAA MM logo on the front with a list of “sponsors” on the back, a la your standard 5K run t-shirt. Hilarious.

We saw Susan, met Viper and Vulcan, and walked around the neighborhood to get the lay of the land – boat docks, beautiful pool, and the waterway that leads out to the Gulf of Mexico. Yes, Gulf of MEXICO.

We headed down to Duval Street, walked around a bit, and then got some lunch and drinks at Caroline’s. We scouted some spots to watch games but settled on Ben’s recommendation of Pickle’s. Purdue snuck out with a last-minute tip in to beat Texas and Iowa shocked Nebraska which didn’t really sit well with us. However, there were fan representation from both winning teams and a woman next to us was so happy Iowa won (her daughter is a student), she bought us all spicy pickle shots (pickle juice + vodka). Go Hawkeyes!

With all of the excitement of being together and the second weekend of Madness, I didn’t pace myself in terms of food and drink, so I was pretty “exhausted” when I realized there were two more games! We left Pickles and walked on to Durty Harry’s to watch The Durtbags (a local favorite band of Ben’s). Ezra and Mark found a spot to follow the Illinois/Houston and the Arkansas/Arizona games while Ben and I stood for a bit watching the band. After a few songs, we all decided it was time to get back to Ben’s place. We watched the end of the games there, happy that the teams we were rooting for and betting on won and covered.

Friday morning was a lazy start and I took advantage of Mark’s camping hammock to read, rest and enjoy the sun. Ezra went off to run and exercise while Mark and I went for a long walk along the seawall, met up with Ben along the way, and caught up on all of life’s latest.

We grabbed Ezra and went to Goldman’s Deli for lunch/brunch. A promising start ended in some chaos with our friendly waitress, “Big Blue Sue,” a friendly and chatty New Jersey native who proceeded to get several key elements of our order wrong – mostly related to Ezra’s bagel and the latkes we ordered.

We then headed to Fort Taylor beach and roasted in and out of the water for a while. Very therapeutic, as Ezra put it. Then we zipped around Duval again to scout a bar that would promise to a) show all the March Madness games and b) play TV volume instead of bar/live music. We landed on Jack Flats which turned out to be a solid spot with good food, drink and volume on the TV (at least via the little box we secured for our table that could dictate which TV we listened to. We’ve been doing this for over a quarter century. How come we never thought of inventing that device!?).

We settled in to catch the UConn women put in a “lukewarm” performance and still beat UNC by 21. Then it was time for the Duke v. St. John’s showdown, in which St. John’s dominated for a good portion until Duke somehow pulled out the win. Unfortunate, but at least it was close enough to cover all our bets. The second game was Michigan v. Alabama and it worked its way out as we expected with Michigan winning (and covering) comfortably. We decided we wanted to watch the UConn v. Michigan St game back at Ben’s place, so we got an Uber as soon as the Duke/St. John’s game was over and made it back in plenty of time.

Again, the drinks effected my memory of the game, but it was close throughout and UConn only escaped after a few key free throws down the stretch to win by four. We didn’t really pay too much attention to the Iowa St v. Tennessee game, because we were focused on UConn, but just as UConn was keeping my brackets alive on one side, Iowa St. was dashing my hopes on the other. Tennessee won handily and my Iowa St. “sleeper” win in several tournament pools feel apart.

Saturday was deemed “Sports Day” as we intended to wake up and go play basketball AND pickleball, but we ended up sleeping in and limit ourselves to a new pickleball tradition. It was only last year that I had developed a gimmicky online “decision-a-tor” where I mocked our choice to abandon basketball and finally cede to the gentler, more “age appropriate” options of golf or pickleball, and, yet, here we were. Mark is still nursing Achilles tendonitis, so he wasn’t keen on pushing it, but pickleball seemed manageable. Ezra and I had played before, but Mark and Ben were total newbies. Regardless, they insisted on being a team. They picked it up quickly, although Ben struggled with the weird scoring. Ezra and I dominated, but Mark and Ben’s competitive nature came out and they insisted on “just one more game,” so “best of 3” became “best of 5” became “best of 7.” We also realized that the reason the courts were available was because the smart, old folks play early, before the scorching sun, so I got a whole lot of color regardless of my spray-on Coppertone.

We headed back to Ben’s after a quick stop at Publix to buy provisions to make deli sandwiches for lunch. Mark and I followed up lunch with a trip to Ben’s pool where I was hoping to nap, but it was too hot. We sat in the warm-ish pool talking about life stuff – kids, retirement, the way the world was collapsing around us, etc. My short attempt to relax in the sun ended pretty quickly as I felt like a rotisserie chicken after about fifteen minutes.

The games were a little earlier Saturday night, so we made our way down to Duval and grabbed a table at Jack Flats again for the first Elite Eight games, Arizona v. Purdue and Illinois v. Iowa. The Boilermakers held their own in the first half, but Arizona put in another gear in the second half and won by 15. Illinois did much of the same and rolled over Iowa by 12. I didn’t have much riding on those games, but fun to sit and cheer on with the gang.

While this trip has always been pretty insular – we’ve agreed not to expand the guest list beyond the original five – we did allow a guest for a limited time at Jack Flat’s. One of Ben’s good friends, “Nebraska Jim,” surprised us all by walking into the bar, “recognizing” Ezra and giving him a big surprise hug. Ben told us Jim might join us for a while, but the intro was classic. He’s a real nice guy and fit right in, but as soon as his allotted hour was up, we kicked him to the curb (just kidding, he left of his own accord).

I honestly don’t remember if we did anything after those games, but assuming they ended late, I’m sure we Ubered back to Ben’s and crashed.

(SIDE NOTE: Ezra spent a good portion of the trip on a hunt for a specific KW hat he saw on a guy in the airport when he arrived. All we know is it was orange with some kind of fish fin/bone/silhouette. We never found it, but I did find a substitute that I thought might be suitable for him ;))

Sunday became the true “Sports Day,” as we hustled out to a local basketball court – Mark and I walked. We struggled through just one game of “21” with Mark as an “automatic point guard” who we could pass to in order to try and free ourselves for open shots. By the end, Ben and I were so gassed that we were rooting for Ezra to win and put us out of our misery. Pretty pathetic, but fun nonetheless.

Of course, next stop was more pickleball with Ben and Mark determined to avenge Saturday’s drubbing. As Ezra and I are just as competitive as those two, we were determined to dominate again, which we did. However, Ben and Mark both vowed to play regularly and so I’m sure this will become a new battle for us in years to come.

We planned our logistics pretty well after that. We were across the street from a small beach, so Ezra and I jumped in the water; Ben showered, then I showered and I changed. We drove down to the famous “Southern-most point in the US” and snapped a few pictures in our “Mensch Madness” t-shirts. Then they dropped me off at the Hemingway House while Mark got a Cuban sandwich and they went back to Ben’s. The first games – UConn women v. Notre Dame and Michigan v. Tennessee were starting.

The Hemingway House was a typical “old house maintained” type of a museum. Modest house by today’s standards, but interesting in the history of it and Hemingway’s time there. The place also has 59 cats in residence, so that was cool. I was a bit dehydrated and had taken in too much sun from basketball and pickleball, so I wasn’t completely in the museum mood. I also had my eye on the clock, because I wanted to get home in plenty of time for the UConn v. Duke game.

I Ubered back to Ben’s to learn UConn women won fairly comfortably and Michigan didn’t have any trouble with Tennessee.

…and then there was UConn v Duke. A horrible struggle for UConn against another loaded Duke team. We were down by 19 and looking like that wasn’t the bottom. A ton of missed threes, a lot of fouls, and Duke’s Cam Boozer doing pretty much what he wanted.

However, you may have heard how that game wrapped up. ;)

I sat there convincing myself that if we could shave off a point or two every minute we’d have a chance. And that’s exactly what we did. Somehow, we down by 2 with :10 left. But even then, there was little hope – it was Duke ball and all they had to do was get the ball in and hold it until they got fouled. They didn’t even have to get it over half court. But one thing led to another, as it tends to do at this time in March, and we all went wild when Braylon Mullins hit a historic 3 from mid-logo with :00.4 left on the clock to give UConn a one point lead and the win. We re-watched several times to make sure it really happened and to revel in the beauty of a) getting to another Final Four, b) a game-winner for the ages, and c) beating Duke.

We found a nice restaurant with a patio to celebrate – in a remarkably mature way, now that I think about it. Most of the conversation was focused on the win, the shot, and sharing all of the social media angles and reactions. Of course, we dipped into the recurring subject of how to figure out a way to live closer, extend this weekend trip, see each other more often, etc. Always bittersweet to have to say goodbye to these boys.

Monday was early for me and Mark, so we could catch an Uber to the airport and catch 7am flights. The trip and drive back were easy and blew by – buoyed by the thousand or so times I rewatched the end of the UConn/Duke game ;).