Thursday morning, we got up and headed to the pool deck for breakfast. They had a counter set up with the typical hotel fare: toast and bagels, bananas, some pastries, and yogurt. Eating outside on the patio made it a lot more exciting, though. We picked up the in-laws from their hotel room (they’d eaten earlier, of course) and crossed the street to visit the Hemingway house.

We opted to walk around ourselves rather than go on the tour. It was a really hot day, so being in a crowd in those only fan-cooled rooms seemed like a little much. The cats didn’t mind at all… I liked this guy hanging out on Papa’s bed:

We toured the entire house, then the grounds, including the cat cemetery. I tried not to look too closely.

There’s a good view of the lighthouse from the upstairs balcony. Key West legend has it that Hemingway liked living across the street from the lighthouse, because he never had trouble finding his way home from the bar at night.

His office is in a building out behind the main house, and it’s my favorite. It’s covered in souvenirs from his travels all over the world.

Bally got to meet one of his cats, too, who wasn’t terribly interested in having a basketball hanging out with him.

We stopped in the shop, picked up some souvenirs, and dropped them back at the hotel. Then we walked a couple of blocks down Duval to the Conch Train stop, and purchased tickets. It’s not generally the kind of thing Matt and I would do (especially after having been there a couple times), but my parents enjoyed it quite a bit, and at that point Matt’s parents welcomed the opportunity to be off their feet for a while.

The tour ended up being really interesting, and we visited places on side streets that we hadn’t seen before. We also learned a LOT about Key West history. It took us down to Mallory Square, where we had an obligatory stop at the shops and restrooms there. We decided to get lunch, so we walked over to Island Dogs nearby. (Note: do not make the mistake of going to Island Dogs. The food and service were both godawful.)

After lunch, we boarded another Conch Train for the rest of the tour, which takes about 2 hour or so total.

I thought the second half was more interesting, since it went into some of the newer parts of town, and farther from Duval and the wharf area. We saw a lot of really interesting houses, and noted that Key West LOVES Halloween – everything was decorated like crazy. At this point, Matt’s dad was already dozing off on the train, so I’m not sure he saw much of the tour. When we arrived back at our starting point, we hopped off and went into the hot sauce store nearby for a tasting. (We ended up bringing three bottles home with us.)

After that, we walked back to the hotel to relax for a while. We made drinks in the room, and then went to play cornhole while Judy watched and Harlan napped. The little backyard of the hotel is seriously great, and the lighthouse and huge tree provide a lot of shade.

Judy decided to go take a nap before dinner as well, so we made plans to come back and pick them up at 5:30 to go for sunset and dinner. Matt and I walked down
Duval in the other direction, stopping into a few stores to buy sandals and souvenirs. Then we headed to Rum Bar in the Speakeasy Inn, one of the best places we’d stopped at on our previous visit. This time, Bahama Bob himself was tending bar! We welcomed his advice on our rum flight, which was served up in a barge.

(We had Botron, Angostura, Diplomatico, and the two on the right are Hemingway-tribute rums called Papa’s Pilar, so obviously we were thrilled about that.)

Once our rum was finished, Matt became intrigued by the repurposed Carlo Rossi jug behind the bar labelled “Bob’s Bark Juice”. Bob explained that it was infused with a bunch of bark and herbs, so it’s basically just like Mama Juana from the Dominican Republic. (It’s also made with 150-proof rum.) Matt ordered one, and I declined, though I did try it. There’s some flavor in there that I can’t get past, and I wish I knew what it was. Also, that meant that Matt was in GREAT shape by late afternoon.

We walked back to the hotel to retrieve the in-laws, and of course mix a drink for the long walk to Mallory Square. On the way, we met this ibis hanging out overhead, probably trying to poop on us.

We stopped into Captain Tony’s for a beer, because we really wanted them to see that place, too – it was the original location of Sloppy Joe’s, back when Hemingway hung out there, and Captain Tony was his friend. They enjoyed all the bras suspended from the ceiling, I’m sure. There was a guy with a guitar singing for tips at the door, so Judy hopped up and sang a song with him, and then we were on our way to Mallory Square for sunset.

We stopped at the outdoor bar at El Meson de Pepe (because you wouldn’t want to be without a cocktail at sunset), and Harlan went inside to use the restroom. We waited forever for him, and it was becoming clear that he was lost. We walked around for a while, and finally saw him standing in the square, scanning the crowd. We retrieved him in time to take some awesome photos before sunset.

We hung out near Key West Mustafa again, where Bally met the stuffed tiger hanging out on his gear.

Our final sunset in Key West was as good as the rest of them:

After sunset, Key West Mustafa requested some help singing the Banana Boat song, so Judy hopped right up to the microphone and joined a group of women singing backup. Yes, my mother-in-law was busking in Mallory Square, and it was awesome.

We decided to walk back down to the wharf because we’d noticed a bunch of restaurants over there the previous night. I knew they’d all be seafood places, but figured one of them had to have something I could eat; I’ve learned that I can’t really be a picky vegetarian on vacation, especially in places that are really seafood-focused. We walked around checking all the menus, and things weren’t looking promising. We finally decided to go into Conch Republic Seafood without looking at the menu. I figured I would cobble something together, or maybe just have mojitos while they ate.

I ended up with a salad and artichoke/callaloo dip, which was actually pretty tasty. Matt had snapper Wellington stuffed with blue crab. The drinks were pretty good, and we were on a giant patio overlooking the ocean, so it was hard to be too annoyed with subpar vegetarian options at that point. The in-laws seemed to like the place quite a bit, too.

After dinner, we walked back down to Duval Street, which was far more crowded than it had been the two previous nights. Judy had declared her intentions to go hear the song Margaritaville at the original Margaritaville, so we went over there and got a table. A guy was just setting up on stage with his guitar, so we were set. We got drinks, and my mother-in-law got herself one of the shark-fin hats that they were passing around. She was having a pretty good day.

Guitar guy was horrendously boring, but finally he got around to playing her song (after she prompted him some, of course). They danced, and then decided it was time for them to head back to the hotel. We breathed a sigh of relief over being free of guitar guy, and said goodnight. Matt and I walked over to Levity Lounge, and found it in an alley off a side street, attached to the giant Cowboy Bill’s complex (a really dumb cowboy-themed bar that we avoided like the plague). They had a really good beer selection and big TVs showing the Giants/Bears game, so we grabbed seats at a rail in the alley and hung out watching football.

After a couple beers, we got some Appleton in to-go cups from the bar, and headed back to the hotel to sit on the patio for a bit before heading to bed.