In the morning, we unfortunately had to check out of the Southernmost House. (Had I known beforehand it was that great, we would’ve chosen to stay there the whole time. Next visit!) We rolled our suitcases the eight blocks or so to Azul Key West, which I’d picked because it was a little closer to the heart of things. Since we were early we had to leave the bags there, but that was fine. The guy working at the desk was super-friendly, and knew who we were when we arrived. We thanked him and headed to get some food.
Brunch meant an obligatory stop at Jimmy Buffett’s Margaritaville. We had to, because it’s a tradition. (That’s also the first Margaritaville I begrudgingly visited.) We also have a longstanding tradition of bringing home a souvenir shotglass, but we were both feeling the effects of the previous night to much to really want to do a shot. (We ended up buying one at the store afterwards.) They did have Kalik, the beer of the Bahamas, on the menu, so we got that instead. I was excited that Matt finally got to try it!
While we were there, we researched various options for sunset cruises in Key West. We called a couple places, and managed to find one that was available. We made reservations for that evening.
We did some shopping along Duval Street, working our way back down to Mallory Square. Rounding the corner to where our bikes were parked, we wondered if maybe they were actually stolen, as unlikely as it was. But no, they were sitting right there where we’d locked them up, in the same crappy condition as always. We threw our bags aboard and rode them back to the hotel, because it was time to check in.
The guy at the desk had already brought our bags up to the room, which was fantastic. We hung out there for a while, enjoying the air conditioning; it was ungodly humid in Key West right then, and brutal in the sun. I dozed off for a while, and my short nap was very effective at getting me back to 100%. I was ready for some history! We hopped on our bikes and rode over to see the Hemingway House.
We knew about the polydactyl cats there, but didn’t realize to what extent they had the run of the house. They were great, and couldn’t have cared less about the people paying attention to them. They were used to being tourist attractions.
I loved the Hemingway house, even though of course there was no air conditioning and we were sweating through our clothes.
My favorite thing was his studio. It was exactly what you’d expect from Ernest Hemingway.
His pool wasn’t bad, either!
We crammed in the gift shop with all the other visitors, and picked out some souvenirs. I’m pretty sure it was that crowded just because it was the only place with air conditioning.
From there, we rode over to Hemingway’s original Key West hangout: the former home of Sloppy Joe’s (which is now half a block away), Captain Tony’s. Captain Tony was a local character in his own right.
The place was absolutely covered in mementos from people who had visited, and they were aged to the point that you couldn’t tell if there had actually been a fire in there, or it was just years of cigarette smoke. All the chairs were painted with the names of famous people who’d sat there, too.
(I probably don’t need to mention the sheer joy of day drinking in a tropical climate, too.)
There was a really drunk group at the end of the bar trying to figure out what ‘vaya con dios’ meant. We laughed to ourselves about it for a while, and then I told them because I couldn’t take it anymore. They staggered out of the bar, and shortly after that a big group of bros from Jersey piled in. They were even more drunk, celebrating one of the guys’ birthday. (They were kind of a confusing group, too. They ranged in age from questionably-21 to 50ish.) They insisted on tequila shots and a lot of yelling, so we decided it was time to move on. Plus we were hungry!
We crossed the street to Amigos Tortilla Bar, where we both got tacos and beer. From there, we could still hear the bros yelling from across the street. Holy crap. The tacos were awesome, too!
From there, it was time to head up to the dock for our sunset cruise! We got our bikes and rode up to Schooner Wharf. I was very proud of myself for riding with a beer in my bike basket.
We checked in, and the guy at the desk gave us coupons for 2-for-1 drinks at the bar, so of course we had to take advantage of that. I had a Cuba Libre, and Matt got to have his second Kalik of the day. He was very sad about it, obviously:
Once we finished, it was time to board the Schooner Western Union. As we waited in line, they announced that the bar was open right away, so we all headed there for beer. We took a seat, listened to their safety instructions and description of our trip, and then we headed out of the harbor.
The ship was amazing. It was apparently used by Western Union to lay cable as late as the 1970s.
Once we were out of the harbor, we got to help raise the sails! It was way harder than I expected. Not because of the effort, but the speed with which the rope flies through your hands.
In addition to our awesome captain, Len, there was a hammered dulcimer player named Gary. He played sea shanties and told stories about the ship’s history. Seriously, we were dying of awesome.
We sailed past Mallory Square, where a crowd was starting to form for sunset. They took us past the cruise docks, and we saw the beach we’d been at the previous day. Once we got out into open ocean, they told us they were going to fire a cannon, and even picked out a catamaran to fire it at. It was a tiny cannon, but it was incredibly loud.
And then, after firing the cannon, there was a HOMING PIGEON. Gary brought out a basket and said he was going to release the bird, so we should have our cameras ready since he’d fly away quickly. He opened the basket, and the bird’s head popped out, looking around. Then he hopped up onto the edge of the basket, and just sat there. Gary was kind of embarrassed after the bird hung out for a few minutes, but it meant we all got a bunch of pictures. He finally took off, circled a few times, and headed back toward Key West.
The ship turned to head back toward the harbor, and Matt and I got ourselves some champagne for a toast. Just like the night we got engaged in Maui!!
And then it was sunset time. I think if I lived in Key West, I’d have to go watch it every night. I don’t know how that could ever get old.
On the way back, they explained the presence of the gigantic ship lurking nearby: it was the Discovery channel crew filming for Shark Week! They have a bunch of smaller boats that go out to sea, and they’re lifted back up to the deck of the large ship at night.
By the time we got back to the pier, it was completely dark. We went back to Schooner Wharf for another drink, and to work out our evening strategy. (We were working from a list of the most historic/interesting bars in Key West, so getting to them all required some planning.) We got our bikes, and rode down to Duval Street to park them. We were about a block from the Hog’s Breath, so we decided to try that first.
We ordered food and a drink and hung out for a while, but the place was a little too quiet for our tastes (it’s Duval Street… you want it to be crazy). We decided to give the Green Parrot a try, as it was another old Hemingway favorite. The bar was unfortunately too full to sit at, but we got a table where we could overlook the scene. Their Cuba Libres were delicious, apparently:
And because you can’t possibly stay away from Sloppy Joe’s for too long, we ended up back there around 12:30. We hung out at the bar with some Sloppy Ritas, watching the same cover band from Philly. They were great.
And then it was time to take our bikes back to the hotel, which seemed like quite a feat. I decided to give it a try, and the worst case was that we’d just have to walk them. I made it within a few blocks at the hotel before tipping over, but we were stopping at an intersection, so no damage was done. So riding bikes drunk is definitely possible, but I also wouldn’t recommend it. Especially if you’re me and are prone to amazingly bad balance as it is!