For the first time ever, we decided to take a trip with my in-laws. I was worried that it wouldn’t work out well, but they turned out to be great travel companions! We flew into Fort Lauderdale, took them on a whirlwind tour of Miami, and then headed to the Keys. We had two nights at a quiet hotel on the ocean in Marathon, spent three nights across the street from Papa Hemingway’s house in Key West, and then had another short visit to Fort Lauderdale again before heading back.

I could easily live in Key West, I’m pretty sure.

(The entire photoset is here on Flickr.)

Read from the beginning below, or jump to each day:

• Sat 10/5: Over the Rainbow to Florida< /li>
• Sun 10/6: Meeting the Tarpon of the Upper Keys
• Mon 10/7: Bahia Honda: Perfection in the Keys
• Tue 10/8: Our Triumphant Return to Key West
• Wed 10/9: Best Place to be on a Boat.
• Thu 10/10: Hemingway’s Cats and the Rum Barge
• Fri 10/11: Exiting the Keys
• Sat 10/12: A Quick Stop in Kentucky

Matt’s parents had come into town the night before, and we went over suitcase packing with them yet again, since this was to be their first flight in something like 15 years. The main concern was making sure that my mother-in-law didn’t try to take her huge toiletry bag through security with her, so we had to review the 3-1-1 rules multiple times.

We got up bright and early at 6am to get our ride to the airport in style; we had an Escalade from Uber, and an awesome driver named Patrick. There was a long security line which we opted to wait in so that we could escort the in-laws through security, rather than taking advantage of our PreCheck access. That was a little painful, but the trip through was entirely uneventful. We had some time to kill before the flight, so we got coffee, pastries, and a breakfast cocktail at Surdyk’s before heading to the gate.

The flight boarded early, so we were able to get on right away when we arrived there. Matt and I had a two-seat row to ourselves, and the flight was uneventful. We ate sandwiches from Surdyk’s and enjoyed the view of the coast. As we approached Fort Lauderdale, we flew right over a rainbow!

 
We circled over the Everglades before heading into the airport from the west. I really love this view, with the houses pushing right up against the alligator zone.

We landed around 1:15, then went to get our bags and board the rental shuttle. I was renting with Hertz for the first time, because I’d gotten a deal through American Express for 5,000 Hertz points for $250. We only needed 2,500 for the week-long rental, so that means I have another free week still waiting for me. That was a hell of a bargain!

I found my name on the board at the rental place, and we rolled our bags out to the car. It was a gigantic Buick Verano, so we were rockin’ it just like old people. I hate driving cars that large, but it was definitely comfortable for the four of us.

We left the airport and drove straight to Miami Beach to get lunch. Huahua’s Tacos did not disappoint, and we were able to sit out in the sun. It was a nice change, having left Minneapolis in the early fall. I especially enjoyed the world’s greatest guaco, which had both guacamole AND a slice of breaded, deep-fried avocado. So delicious.

There we had our first of many toasts to Southern Florida, too:

 
After lunch, we drove over nearer South Beach and circled for a while looking for parking. We finally found a ramp that didn’t cost a million dollars, and that was only a few blocks from the beach. Harlan and Judy have never been to Miami, so we wanted them to see the monstrous beach where we both misplaced our underpants on our honeymoon. (We left that part out of the story.)

After that, it was critically important that they visit the other best thing in South Beach: Mac’s Club Deuce. There were a few people sitting in there when we walked in, and they’d all clerly been there a while. My favorite was a completely tattoo-covered guy with an eyepatch, who managed to take a nap at the bar with a drink and a shot sitting in front of him. (We later walked past the tattoo shop that he probably owned around the corner.)

 We ordered drinks from the awesome bartender, who gave us each a poker chip, good for our next drink free. Daytime 2-for-1s? Sold. (They’re not weak, either.) We sat there enjoying the divey ambiance, and Matt got into a conversation with one of the old guys holding up the bar, based on their mutual love for Hunter S Thompson. The guy instantly became his BFF, and came over to tell him stories about his old days in journalism. It was hilarious.

After we finished our second round, it was time to head out lest we just decide to move in there. Matt bought a t-shirt, and they gave him a bunch of stickers as well. We retrieved the car and headed up the A1A in the direction of Fort Lauderdale. We could’ve taken the highway, but there’s a lot to see on that route. There’s something about that oceanside ridiculousness that I love a lot.

Once we got tired of the stop-and-go traffic, we headed back toward the interstate. At that point my father-in-law was napping in the back, so we figured it was a good time to go check into the hotel (it was around 5pm). We took 595 over to Plantation, a suburb west of downtown Fort Lauderdale, and managed to locate the Sheraton Suites. From what we could tell, the entire town of Plantation is one gigantic strip mall after another, and the hotel was no exception: it seemed to be located right in the middle of an abandoned mall. It was really nice, just a little strange.

The in-laws wanted to get comfortable, have a brandy (they brought their own bottle from Minnesota, fearing that E&J – the only brandy Judy will drink – would be in short supply in Florida), and take showers. Judy swore it would take her an hour to wash and do her hair, which seemed unlikely. Matt and I were ill-prepared for room-based relaxation, since we had brought nothing to drink from home. We dropped them off, looked up the location of the nearest liquor store (shocker: it was in a strip mall a mile away), and headed over there to get some room beers.

The place we found had an incredible beer selection, so we built a couple of our own 6-packs (a combination of local stuff and other things we hadn’t seen before, plus Dragon Stout, which we thought was only available in Jamaica!) and headed back to the hotel. We opened the suitcase but didn’t bother unpacking, since we were only spending the night. The room was fantastic, too: there was a big living/work area with a sideboard, a huge bathroom and closets, and a separate bedroom with a second TV. How many hotel rooms have a hallway? (The place isn’t convenient if you’re planning to spend a lot of time in the FLL area, but it’s great if you want to be near the interstate that will take you to the Keys with the least painful traffic congestion.)

We hung out for a while, then went to check in on Harlan and Judy in the room next door. Judy had changed to her going-out outfit, and they were enjoying a brandy. We talked about dinner options, and researched a couple spots where Matt had found vegetarian options on our phones. We finally decided on Seasons 52, and I called to make reservations for 8:30. Then we gathered our things and headed that way.

The restaurant was about 12 miles away near the beach, but it took a while to get there because the only direct route was on local streets. We finally managed to locate the mall where it was located (surprise!) on Highway 1, and parked in the nearest lot. We walked through the mall looking for it, and finally had to ask for directions. The entrance ended up being down a level and outside, near the other typical mall restaurants. We checked in with the host stand and stood around listening to the piano guy playing in the bar. The place was gigantic, and it was surprisingly packed, too.

We were seated, and attended to by a very unpleasant server. He was incredibly slow, and also impatient with my in-laws. While the food was seriously excellent (I had a vegetarian platter with a grain salad, cedar-roasted tofu, chutney, roasted vegetables, and a delicious taco), the service was unbelievably bad. I guess that’s what you get for going to a big chain restaurant in a mall in Florida.

We fixed it afterwards, though, because then it was time to go to Mai Kai, one of the greatest tiki bars on earth. We were worried that it would be really busy, and that was backed up by the huge crowd standing out front as we arrived. It turned out that it was the crowd for their nightly luau show all waiting for the valets, and the place was actually nearly empty. (We even got to park our own car!) We got a table and ordered a round of drinks. Matt’s Jet Pilot was amazing, and incredibly strong.

Harlan went to the bathroom and reappeared a long time later. He told us his zipper got stuck in the down position and he couldn’t fix it, so he finally asked the bathroom attendant if he could help. The attendant told him to hold the bottom of the zipper and tug; that worked, so he tipped the guy a dollar for the advice. (At this point in the story, we were all falling off our chairs laughing.) He also got lost leaving the bathroom, and told us he wandered all over the restaurant (it’s made up of several gigantic rooms, all decorated differently), and finally ended up crossing a bridge and ending up in a rainforest. We had no idea where that was, because we’d only ever seen the bar.

Unfortunately we couldn’t stay very late (his parents looked like they were going to doze off), but we were happy to get in a visit. While Judy and I were waiting for them to finish up, one of the hosts asked us if we’d seen the shrunken head yet. I had no idea what that was about, but since we’d already decided we had to make a return visit on the other end of the trip, I put it on my to-do list.

We headed back to the hotel, and the journey seemed a LOT longer on the way back. We finally got to the hotel, and headed to our rooms for the night. Matt and I enjoyed a delicious Abita Pecan nightcap before going to sleep. Hooray, vacation!

We got up at 9 Sunday morning and checked out of our abandoned-mall hotel. We found a Dunkin Donuts a mile away for a quick breakfast and coffee, and then we hopped on I-75 to head to the Keys. Considering the usual traffic in Miami, Sunday morning was the absolute perfect time to go. It was smooth sailing the whole way.

We got to Key Largo around 11 and stopped immediately at the visitor center. I’d printed Florida Rambler’s excellent mile marker guide, so we followed along with their recommendations, too. We picked up a bunch of tourist magazines (I can’t resist the coupons) and talked to the lady at the counter about her recommendations for things to do. She ended up being pretty dead-on as far as the awesome things in the Keys, too.

A couple miles down the road was the famed Caribbean Club from the movie Key Largo, so we stopped in for a beer, and to get Bally’s photo with the wooden Humphrey Bogart out front.

The interior was full of memorabilia, but the in-laws seemed to not notice that. We headed right out the back to sit at a picnic table overlooking the Gulf of Mexico, which was just fine with me. I could spend an entire day like that, really. (I believe I have, in Jamaica.)

There were no servers evident, so the men went to the bar. They returned with the best beers they could find there, which for Matt and I meant Budweiser (a.k.a Bud Heavy) in cans. They said the bartender was surly, too. At least the place was in a great spot!

Once we’d examined our various maps and finished our beers, we got back on the road to go another few miles south to Ballyhoo’s, one of the places listed in our guide. I’d seen mention of an entire vegetarian menu on their website, so it was a great option in a place not really known for being very food-progressive. We got a table on the patio under a tree strewn with fishing floats, which I loved.

Apparently we were sitting under a pitch apple tree, because these things were scattered around the place. I didn’t know what they were until we asked our server, and she told us they were inedible but pretty when they bloom.

We ordered beers and the best possible appetizer in the south: boiled peanuts. Everyone else was wary of them, but they reminded me of the first ones I’d had from a highway-side stop in Mississippi. I got to have my first nearly-local beer, too!

They had incredible jalapeno cornbread, and I had a sweet potato burger that was so gigantic I took the bun off and just ate the whole thing with hot sauce. It was awesome.

From there, we headed to Robbie’s Marina, because you can do THIS there:

And for three dollars, you get this bucket of fish for it. While ordinarily I will shy away from touching any dead animal (I’m vegetarian, after all), in this case I wasn’t passing up the chance to feed a gigantic tarpon.

The second we set foot on the docks, we met this guy. There’s a sign about not feeding the pelicans, because apparently they’re jerks and will bite. Still, they’re hilarious!

We went down to the end of the dock, and saw massive quantities of tarpon swarming around. It’s hard to photograph them, or to even get a sense of how big they are, but some of them were easily 3 feet long. We’d meet a guy who said you could hold the fish well up in the air and a tarpon would jump up and grab it, but they didn’t seem terribly interested in that. We had to hold them within a foot of the water, and then the tarpon scramble would begin.

The pelicans hang out nearby, watching warily. There was a couple there who’d clearly had several beers, so they offered no end of entertainment: first the girl was talking with a fish in her hand and not paying attention, and a pelican came hopping up sidelong behind her and almost stole it. Later, a seagull swooped down and grabbed it right out of her hand. So funny.

Once our fish bucket was empty, we went to hang out in a double adirondack recliner while Judy shopped. I just wanted to stay for a long time, because it was very Caribbean there. When the in-laws were ready to go, I stopped and bought a coconut birdhouse to take back home, and then we were back on the road.

We headed to our hotel to check in, since it was nearing 3pm. The place was Rainbow Bend on Grassy Key, which is just south of Islamorada and north of Marathon. We’d picked it because it was relatively cheap (everything in the Keys is expensive, so it’s tricky), and because they let you borrow their boats to take out during the day. Plus it was right on the Atlantic, and I figured we could grill on the beach.

We pulled up, and Judy freaked out because there was a pigeon walking around outside the lobby. (She’s deathly scared of birds.) The lady came out and said hi, and then shooshed the bird (who she called Roscoe!) away. We checked in, and she said would basically had our pick of rooms. She took us around to show us three options, and we chose two decent-sized rooms next to each other in an unattached building facing the swimming pool. Our room was slightly smaller and had saloon doors to the bathroom, but the shower-in-a-hot-tub made up for it. We had a small fridge, table, and coffeepot, and that was all we needed. The room was dark and seriously outdated, but it was clean.

Harlan and Judy’s room was much bigger and brighter, and they had a full kitchen. That suited them a lot better, so it worked out well. Both rooms had patios overlooking a yard full of tiny lizards. We changed into bathing suits, put some beers we’d picked up into a small cooler, and headed to the beach.

The beach, however, was not exactly what I pictured. The sand was hard, and there were huge mossy boulders at the water line. The tide was out, so there was no way you could get in there without doing damage to yourself. It was kind of stinky, too, due to the buildup of stuff in the next yard over that accumulated at low tide. The grilling area was in pretty rough shape, too. But we were on the ocean, so whatever. We went to swim in the pool instead.

The place seemed deserted, and there were apparently only a couple of other rooms occupied. It was still shoulder season in the Keys, but this seemed especially quiet. They had an onsite restaurant that was apparently popular, but we never saw more than four cars in the lot at any given time.

We hung out in the pool drinking beer for a long time, then went to go rinse off and change for dinner. One of the people we’d talked to at the Caribbean Club recommended the Safari Lounge (he said the locals called it the Dead Animal Bar due to the big game trophies), so we headed up to Islamorada. We found the place attached to a fancy resort near the docks, and it looked perfect:

Inside, however, was a different story. It basically looked like a Wisconsin bar (including the dead animals), and was ten times as smoky. The bartender couldn’t make anything better than a rum and coke, even though it was a tiki-style bar on the ocean. We took our drinks outside to sit on the patio for sunset, which was really pretty.

After that, it was time for dinner. We drove right up the road to Habanos, a Cuban restaurant right on the Overseas Highway. It was too-brightly lit and the interior was tacky, but it was proper Cuban food, and that was exciting. I had to have a cortadito ASAP.

Because it was proper Cuban food they of course had nothing traditional that was vegetarian, but we had a tostones appetizer and I got a small veggie pizza that was actually really delicious, so I was happy.

On our way out, we decided we should stop at a liquor or convenience store for some beer to bring back to the resort for card-playing. We headed south, passed our hotel, and crossed into Marathon proper before even seeing anything that was open. It was 8:30, by the way. We finally saw a gas station, and ran in to find they didn’t sell beer. The cashier there said to go to Walgreens a mile south, so we did that. They had a separate liquor store with a surprisingly good selection, so we grabbed a bottle of rum (which came with free pop) and some beer. The guy at the counter made fun of us for being Minnesotan (re: living in igloos), and I told him we at least didn’t have hurricanes. He gave a loud PFFT and said, “Did you see how all the buildings are built around here? They’re all on stilts and nothing’s more than three stories high!” He had a good point.

Harlan and Judy were in the main part of the store getting snacks, so we met them and headed back to the hotel to play cards in their room. Normally Matt and I prefer staying out later with the locals, but this was the kind of place where nightlife is scarce. (That’s what Key West is for.) After the in-laws got tired, we went to our room to play dominoes on the patio. Which was a bad choice without bug spray, as I’d realize in the next few days. But that’s for later.

Monday morning, the in-laws went to partake in the free breakfast at the onsite restaurant. We’re not really breakfast people, so we chose to sleep in and make coffee in the room. They came back with a bunch of gossip from the restaurant owner, who is apparently different than the guy who runs the resort. He had no end of complaints about how the owner had no interest in upgrading the place at all, and just wanted to make money off it. Which is sad, because it was a beautiful location with a ton of potential.

The beach didn’t look so bad in the morning. Still no Jamaican beach, but it looked more swimmable at high tide. The waves were really rough, though, so the guy who ran the boats said it was unlikely we’d be able to go out that day. Which was fine, because we had other plans involving the ocean.

We drove south into Marathon and stopped at Publix to buy a styrofoam cooler and picnic food. We got crusty bread with cheese and cured meat, grapes, snacks, beer, and water, packed everything up in the car, and drove to Bahia Honda State Park.

The park map showed two beaches, so we picked one and headed that way. It turned out that there was just a parking lot separating the two of them, one facing the Atlantic and one facing the Gulf. We decided to check out the Atlantic side first, so we grabbed all our stuff from the trunk and climbed over the dune to find this:

The beach was gorgeous and uncrowded. Judy and Harlan set up towels and parked themselves on the beach with beers, while Matt and I took ours in the water. It was so nice there, I didn’t even care about our less-than-optimal hotel beach.

We bobbed around for a while, and ended up talking to a guy from Madison, Wisconsin (we always meet people from Wisconsin on vacation, and I’m not sure why) who said he and his wife were camping there at the park. They had to make reservations a year in advance, and the place fills up within a few hours of the reservations opening. I wasn’t surprised at all. He said they once made the mistake of not setting up their tent on the provided pad, and his wife had chigger bites so bad she had to go to the hospital. Wow.

After a while, we went to grab masks and my snorkel. The waves were a little rough because of the storm offshore, but I couldn’t believe how much life there was even within ten feet of the beach. I saw a few live conch, too! As requested by the state of Florida, I left them alone to crawl around the sea floor.

After snorkeling and exhausting ourselves swimming back to the beach against the current, we decided to go over to the other side of the peninsula and have our lunch. We found a picnic table with this view, so it was obviously the perfect spot.

The west-facing side of the park features the old railroad bridge that was originally the only way to travel down the Keys over land. It makes for a really picturesque view, too. The overseas highway isn’t pretty, but it’s a fascinating structural feat.

After lunch, we walked up to see the railroad bridge up close.

This is the gulf-side beach from above. It seemed to be more crowded than the Atlantic side, and the water wasn’t as clear.

The in-laws went to wander around and see the historic sites while Matt and I went for a swim at the beach. After a while, we headed over to the shower building to clean up and change, and then we were back on the road heading north over the 7-mile bridge. I wanted to do some shopping, so we stopped at the sandal shop, and at a giant shell store in Marathon to pick up souvenirs. While we were there, we asked the girls working (who I’m pretty sure weren’t old enough to drink, but whatever) if they could recommend a good tiki bar in the area. They gave us a couple options, and we headed out.

Tiki bars are tricky in Florida, because that’s their name for everything with a thatched roof, as far as we could tell. You’re sometimes lucky to find a place that can make you a mojito, much less a classic tiki drink. At that point, I just wanted a bar where we could sit outdoors and have a pina colada.

One of the places they recommended was Lulu’s, right down the street. It’s a restaurant in a cute house, but the main attraction for us was the gigantic round tiki hut in the garden next door. It reminded us of our favorite spot in Negril, 24/7 (R.I.P.). We parked in back and chased off a few big iguanas from the yard, then got seats at the bar. The bartender was a quiet older guy who warmed up once my in-laws started talking to him. We all ordered boat drinks, and Judy and I got the pina coladas we wanted.

After a while, I went to check out the garden. It reminded me a lot of Just Natural in Negril, and there were iguanas and geckos hanging out all over the place. Even though the garden is right near the road, it’s a really quiet little oasis. I would love to have a place like that someday.

The in-laws wanted to go back to the hotel for a mid-afternoon nap, so Matt and I dropped them off and headed back to Marathon. We stopped at a combination deli/liquor store and stocked up on supplies for later, then drove back down to the beginning of 7 Mile Bridge. There’s a small parking lot where you can stop and walk out onto the old bridge, which runs alongside the new one. It extends to Pigeon Key (which you can still only visit via boat, unless you want to bike or jog there), and then there’s a gap before it continues on alongside the modern bridge.

We walked out on the bridge for the view, and to watch the Atlantic and Gulf run together. That looked kind of turbulent.

Afterwards, we drove down around to the other side of the bridge to visit Sunset Grille. The place looks like a gigantic tiki hut, so of course I took note of it every time we drove past. We got mojitos and Matt ordered smoked fish dip, which is something he and his parents would end up eating about 10 more times on the trip.

We sat at the rail overlooking Seven Mile Bridge, the ocean, and a giant patio with a swimming pool, a smaller tiki bar, and what appeared to be a movie screen. It was basically the template for the bar I went to own someday.

We had another round just to sit there enjoying the view, and then it was time to head back to the hotel to pick up the in-laws for dinner. We headed back down to Marathon to Island Fish Company, another place that had been recommended to us more than once. We were seated on the patio right by the docks, and ordered mai tais. Our server was awesome, and told us he used to live in the Twin Cities, working for Northwest Airlines. Now he splits time between the Keys and Maui. (Matt and I died of envy at this point.)

They had a veggie burger on the menu, which made me pretty happy. Also, the view did not suck at all:

Before leaving, we got our server’s advice on bars where locals hung out, and that were unlikely to close at 8pm. He recommended Brass Monkey as the place he hung out most often, because they have bands all the time. When he told us it was in the strip mall behind the K-Mart, Matt and I knew that was a place we had to see.

If you picture what a bar in a strip mall might look like, you’re on the right track. It was dark, smoky, a huge dive, and had a fantastic jukebox and cheap drinks. I cringed when my father-in-law ordered a stinger, waiting for the bartender to ask what the hell he was talking about. But he was very professional, and said “sure!” and headed to the back of the bar where we saw him quietly asking the other bartenders, who I’m pretty sure Googled it. Awesome.

There was Appleton VX and Bubble Butt on the jukebox, and nobody even seemed to care when Harlan went to play a cheesy country song. I wanted to stay there forever, but of course we had plenty to see before noon the next day.

I woke up at 8:30 Tuesday morning covered in bites from what was presumably the largest swarm of mosquitos in history. (Possibly they were chiggers or something beach-like on that order, but I’m not sure. All I know is that I wanted to scratch off all the skin on my legs. It sucked.)

We checked out of our run-down resort and hopped on the Overseas Highway. We crossed back over Seven Mile Bridge and passed Bahia Honda, then crossed into Big Pine Key. As soon as you’re over the bridge, there are fences on either side of the road; that’s to protect the Key deer, which are just miniature version of real deer). They’re only found in Big Pine Key, and they’re very protected. There are signs everywhere about their extremely low speed limit, and stories of people being pulled over all the time. I was dead-set on seeing one, since I hadn’t on our last trip through.

Shortly after crossing the bridge, I saw the back half of one of them pressed against the fence, so I felt like that was a good sign. The lady at the Key Largo welcome center said they just wander all over the neighborhoods in the Key, so I turned onto a side street and we started driving around slowly. The key is densely tree-covered, so it seemed like it would be pretty easy to see them in such a protected area, in a driveway or side street. BUT NO.

We drove further into the depths of the key, crossing to No Name key. Mostly I just wanted to see something with that name, but we figured there might be deer there too. But no, just a lot of awesome oceanside houses and swampy, empty space.

We finally decided to just go to the Key Deer center and see them there. We parked and walked up to the entrance, only to find it closed; it’s apparently part of the national parks system, and this was during the government shutdown. Lame.

I resignedly got back on the highway, and we headed south again. Then out of the corner of my eye, I saw something on the side of the road: a Key deer was starting to cross. We stopped and watched it walk across the Overseas Highway. Of course we would finally see one in the most populated area of the island.

After Big Pine Key, there are a ton of bridges and causeways connecting more spread-out and less-touristy islands with awesome names, like Sugarloaf Key, Cudjoe Key, Knockemdown Key, and Saddlebunch Key. There are communities lining the coast with ridiculously giant oceanside mansions and huge boats. I did indeed have some envy over that, but I’d be happy with a very small oceanside house and a smaller boat.

We stopped at the famous Baby’s Coffee to pick up some beans to take home (we loved that some of their blends were Hemingway references), and then crossed over onto Stock Island. Our predetermined lunch destination was Hogfish Bar and Grill, which was hard to locate even with signs AND Google Maps’ help. We finally found it down by the docks, and were thrilled to officially be in Key West.

We got a picnic table and checked out the menu. Of course the only ‘vegetarian’ option was Caesar salad, but I didn’t really care that much. We ordered beer and hung out looking at the docks and the roosters wandering around the dirt road.

After lunch, we drove into Key West proper. There was road construction and traffic was terrible, but we had time to kill before we could check in anyway. We headed over to the fishing pier near Martello Tower, because we’d never seen that part of town before. It was about a billion degrees and humid outside, so the wind on the pier was a nice break. Also, we saw this dude fishing on the rocks:

This is facing the southernmost point in the continental U.S.:

We walked back and headed to East Martello Tower, because I really wanted to see the gardens there.

The man taking admission up front was a Packers season ticketholder. Seriously, they’re EVERYWHERE.

The gardens are run by the Key West Garden Club, and they were fantastic. It’s like a little sanctuary inside the fort. There’s even a huge banyan tree with a doorway in it, and geckos and iguanas hanging out all over the place.

The gardens were quiet and secluded, and the perfect setup for a wedding. There were fruit trees all over the place.

There were a couple ibis walking around, too, and this guy was not happy that we followed him around.

A little light rain started while we were there, but we could barely feel it. We wandered around in the orchids some more, and then went to find the in-laws, who were hanging out inside watching a video about the place.

By then it was time to check in, so we headed over in the direction of the Lighthouse Court. Since it’s across the street from the Hemingway House, traffic around there was insane (it’s always insane in Key West – having a car there is a huge inconvenience), so Matt dropped us and the bags off, and went to circle while we checked in.

The guys at the front desk were incredibly friendly, and gave us 2-for-1 mojito coupons from their onsite bar and a parking pass, since it turned out they had free spaces behind the hotel. We had no reason to use the car while we were in town, so that worked well. I met Matt to go park, and the in-laws went to their room. We had two rooms next door to each other in one of their long buildings on the property.

The rooms weren’t big, but they were very clean and comfortable, and each of them opened onto the deck that led out to the patio and pool in back. Plus there was a cornhole court in the shade of the Key West Lighthouse, and the place seemed really quiet despite being in the middle of everything. Also, you get to see Hemingway’s place every time you walk out the front gate:

We had a drink in the rooms with Matt’s parents, then headed down Whitehead Street to visit the Southernmost Point marker. As usual, there was a line of people waiting to take photos of it, but somehow I managed to finally get one without anyone in it!

From there we walked over to see the Southernmost House, where we’d stayed for our last visit, and then back up Duval Street, past all the shops and restaurants. My mother-in-law is scared to death of birds, but she didn’t seem too bothered by the roosters there. (Pigeons would be another matter entirely.)

We stopped back at the hotel bar to redeem our mojito coupons, and hung out on the patio for a while. Around 5:30, we headed back out and went directly to Sloppy Joe’s, because it was very important that they witness the most legendary Key West bar posthaste. They loved it, of course. And so did we, because they serve Papa Dobles.

It was nearing sunset time, so we got some roadies and walked down to Mallory Square. Judy keyed in on a guy singing reggae, so we stood near him to watch the sunset. He said his name was Key West Mustafa, and he was pretty entertaining to listen to.

After sunset, we watched another busker doing weird ladder tricks with fire, and then walked down Duval Street again to Margaritaville for dinner, because NOBODY loves Jimmy Buffett like my mother-in-law. Seriously, I’m surprised she doesn’t go to the parrothead conventions. According to their website, they had live music nightly at 9:30, but by the end of dinner it was clear that the in-laws weren’t going to make it anywhere near that long. They hopped on a pedicab back to the hotel, and Matt and I set off to wander.

The smallest bar (a tiny walk-up place in an alley) was empty, so we had to stop in for a drink. We asked the bartender where he hung out, and he recommended Levity Lounge. We made a note of that for later, and headed over to Captain Tony’s because it was a lot nearer. It was super-crowded and took forever to get any service, but I did discover that one of their house beers is pretty good.) From there we went to the Rum Barrel, which was surprisingly empty by that time of night. While the bartender set us up for a rum flight, it became clear that they were ready to close. We asked her about it and she said she didn’t care, since she’d be there cleaning up anyway. I like island bars.

Once they closed, we walked over to World of Beer (which I think was new since our previous visit). They had a monstrous and awesome beer list, which of course is a GREAT idea after a bunch of rum. We ended the night with Matt getting pizza at a little shop while I made friends with a girl from Wisconsin across the street from Sloppy Joe’s. As it goes in Key West.

Wednesday morning, we got up not entirely ready to face the day. Matt’s parents were already out wandering around, since they’d gotten in much earlier than us the previous night. We picked up coffee from a crabby Russian girl at a place on Duval Street, and then walked down to Mallory Square to meet them for an early lunch at El Meson de Pepe. Despite it not being vegetarian-friendly at all (what Cuban place is?), I still like it a lot, and was happy with my plantain-nacho-and-capirinha brunch.

After eating, we went to see more of Mallory Square, and hang out with the chickens.

There was a big ship in port, so the shops in the area were fairly busy. We wandered around them for a while, and then headed farther down Duval to see some more shops. As we passed La Concha (which is now a Crowne Plaza, apparently?), I remembered something I’d read on a travel forum about a rooftop bar and overlook. We decided to go in and check it out.

The bar wasn’t open til 4, but the patio was still unlocked, and there were a few people out there at a table. The view was excellent.

Facing Mallory Square:

Duval Street:

The hallways of the hotel are lined with historic photos of Key West and its many celebrity visitors, too. It’s definitely worth checking out!

Since it had been at least an hour since we’d had a cocktail, we stopped in to Willie T’s. I was very excited to be back there, because we’d been there with a group of five on our first visit, but it was closed for remodeling when Matt and I were there for our pre-honeymoon. We grabbed a little table near the tiny stage, and got a round of mojitos.

I tried to find the dollar bill we’d posted on the wall earlier, too, but I couldn’t remember exactly where it was (not surprisingly). There was a guy named Zach playing the guitar and making terrible jokes on stage (including a song about rhyming with Olive, which I’ll probably never forget).

Once we were done there, we walked back to the hotel. My father-in-law wanted to nap, and Matt and I wanted to go for a swim. We got a couple mojitos at the bar and got in the pool. I wouldn’t really call what we did ‘swimming’, though… mostly we floated around with pool noodles for an hour and occasionally had a sip of our drinks. It was awesome. Judy joined us for a while, sitting on the edge of the pool with her feet in the water. (Someday I’ll convince her to actually come in!)

After a shower and preparing a room drink, we all headed back down towards Sloppy Joe’s, stopping to see the Mile Zero marker along the way.

We had drinks and a couple of appetizers at Sloppy Joe’s (including very delicious cheese arepas), then headed in the direction of the wharf. We had reservations on the Jolly II Rover, which I’d booked because we wanted to take them on the Schooner Western Union, but it was being remodeled. This schooner came highly recommended, though, so it seemed like a good replacement. Plus it has red sails!

It’s a smaller boat than the Western Union, so the crowd was smaller, too. Also, it’s BYOB, which means it’s cheaper. We brought a bottle of Filipino rum and some mixers, and they supplied ice, water, and plastic cups. I liked that arrangement a lot.

Captain Rio (really!) was at the helm, and the ship’s owner also happened to be aboard. We headed out about 6pm, and sailed past Mallory Square, which was filling up for the sunset celebration as it does every night.

It was the absolute perfect night to be out sailing. There wasn’t very much wind close to sunset, but there was enough that we could maneuver into a good position without having to use the engine. While we were waiting for sunset, the crew circled around talking to everyone, and we heard a lot of fascinating stories about their jobs and sailing experience. The captain told us all about his spearfishing adventures in the Tortugas, and the ship’s owner talked about why he decided to buy it. We were so envious.

Sunset was fantastic, too. They explained to everyone about the green flash, and one guy on board SWORE he saw it. There was kind of a white flash, but definitely not a green one. (He was probably drinking Filipino rum, too.)

Post-sunset, we sailed back toward the wharf, much closer to Mallory Square this time. Once we got to one of the narrow streets lined with condos and hotels, they fired the ship’s cannon down the street just to make it echo like crazy. It was fantastic.

We docked around 8pm, and headed back down toward the main part of town for dinner. We’d decided on Kelly’s, since Matt and I liked it so much the first time around. The place was not very crowded at all, and we had a nice table out on their giant patio. The vegetarian offerings weren’t that great, but Matt loved his fried chicken and the house beers were good. The in-laws seemed pleased as well.

After dinner, we walked a block or so to the Green Parrot, one of the other oldtimey bars in Key West. It was apparently also one of the few crowded places, which was kind of shocking. We found a small table along a rail and quickly discovered why it was so busy: they have open ukelele jams on Wednesday. There was a group up on stage leading the crowd, and a whole bunch of people with ukeleles down below following along. They were even selling ukeleles, should you wish to just pick one up and jump in. I loved it.

I had never realized that their ceiling was a giant parachute, either:

Matt’s parents headed out after a drink, and Matt and I decided to stick around a bit longer. It started to clear out after the ukelele jam, so we grabbed spots at the bar and hung out. Round about 12:30, we decided it was time to head back so we wouldn’t feel quite so unpleasant the next morning.

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.

Friday morning, sadly, it was time to leave Key West. We had the identical breakfast by the pool again, and then went to check out of the hotel and load up the car. Matt’s dad was driving this time, so that I could stare out the window at the Keys. We didn’t stop until we reached Islamorada, where we’d decided on a place called Shula Burger at the Postcard Inn, because they had a veggie burger on the menu.

The menu, however, did not have a veggie burger, or anything vegetarian at all. Our server explained that they were rebranding. OF COURSE. I ordered a crappy taco salad without the meat, and I was glad they at least had good beer. (Cigar City Helles is great, by the way.)

Matt took over driving, and we headed back up to Key Largo, where we had to stop at Shell World, the giant craft market with the huge lobster out front:

The shops were indeed as touristy as expected, but there was a bunch of cute stuff, too. I finally fulfilled my desire to own one of those colorful glass floats wrapped in rope, too. I can’t help loving cheesy nautical decor.

From there, we went to find the African Queen. There are about 50 signs for it, so it’s easy to find. The dock is next to the Holiday Inn.

I hadn’t seen the movie at that point, so it was definitely not what I expected. They still take people out on this! Having now seen the movie, I know that the boat is in far better shape at this point.

We snuck through the back yard at the Holiday Inn and went to use their restrooms (their pool complex looked really appealing, too), and then hopped back in the car. We made a quick stop at a nearby liquor store to pick up souvenir rum, the same one we’d tried at Rum Bar:

We also picked up beers for the room, and Matt discovered you can buy Cuba Libres in a can!

Then it was time to head back to the mainland. Traffic was pretty light again, and we made it to the Westin right on I-95 in Fort Lauderdale around 5ish. We checked in, and had adjoining rooms again. Matt’s parents got out their brandy, and we opened some beers and started looking on our phones for a place to have dinner. Based on reviews, we decided on a place called Tap 42, about 10 miles away. Then we set to tearing apart our suitcases and repacking them so that our souvenirs would stay intact on our flight.

Matt’s parents had brought their own bottle of E&J Brandy, the only brand Judy likes. Based on their previous experiences in Florida and Alabama, it was hard to come by, so they were prepared. What we’d learned on the trip, though, was that apparently E&J is now distributed in Florida, so that was even the rail brandy at most places we visited. Consequently, they had a whole bunch left and wanted to use it up before we left. Nothing like having a whole bunch of brandy foisted on you early in the evening, before you’ve had dinner.

We eventually headed to the restaurant and parked. We walked around the back to the entrance, and discovered that the place was PACKED. The restaurant itself is pretty small, and apparently it’s really popular with the douchebaggy crowd, because that’s who was on the patio. (Everyone was really dressed up, too, which was strange.) We asked at the desk how long the wait would be, and they said probably 45 minutes. We decided to stay anyway, because it’s not like there were other spectacular options in the area. We worked our way up to the bar where we could find a standing spot, and ordered drinks. Their cocktail menu was really impressive, so Matt and I were happy; the Farmers Market featured bourbon, sage, mango, lemon, and spicy bitters.)

We were only there for 15 or 20 minutes before our buzzer went off, so that was a nice surprise. They seated us at a long high-top table, and handed us menus. I was immediately thrilled with our decision to stay there, because the vegetarian offerings were spectacular. We ordered the vegan ‘ceviche’, which had fresh lychee, pineapple, and avocado in coconut milk, bruschetta with cheese and dates, and then I got a veggie burger with horseradish. That ended up being so big that I had to take it off the bun to eat it. Everything was great, and it made up for the crappy vegetarian food in Key West. (Our server explained that the owner is vegan, so it was important to him to have those options on the menu.)

From there, we headed back to Mai Kai for a victory lap. The place was way more crowded this time around, and the bar was packed. We were able to get a table in the back where it was quieter, though. I had a zombie, which of course was delicious. We unfortunately couldn’t stay very long, but managed to get in a couple rounds before the in-laws were ready to go. On the way out, we asked the guy we’d spoken to on our first visit about the shrunken head, and he said he’d take us there. He headed off through the restaurant, and for the first time ever, we realized just how gigantic that place is. (We’d only ever been to the bar in front, the bathrooms, and the souvenir shop.) There’s a huge room with a stage for the luau – which was going on as we passed through – and then several other rooms decorated in various island themes. And, you know, the rainforest that Harlan ended up in the first time around. We finally made it to the shrunken head room, and he pointed it out to us in a case on the wall. There was a big table of people eating in front of it, so it was kind of awkward. But dammit, we got to see the shrunken head, and it was as creepy as expected.

We went back to the hotel and stopped into the bar to pick up manhattans to take up to the rooms with us. A very drunk lady at the bar commented quietly (she thought) to her man-friend about why people would want to drink something like that when they were in Miami. I wanted to tell her that we’d spent the last week drinking all of the rum in the world, so it was time for a change.

We hung out in Matt’s parents room for a while watching baseball and helping with their brandy stash, and then went back to our room to finish packing and sleep.

We got up at 9:30 Saturday morning and had to repack suitcases since mine was 52 pounds. We worked that out, crammed all our stuff in the car, and headed to FLL. The car dropoff was quick, and the entire thing cost a total of $103 since I’d redeemed points for most of it. We hopped on the shuttle to terminal two, dealt with crappy service at both check-in and security (where my mother tried to carry through three bags of toiletries), and finally got to our gate.

We picked up coffee and bagels and then ended up at the airport bar for a morning beer. Boarding was quick and we had a 2-seat row to ourselves, so that was good. And as a bonus, we had a layover at CVG, which is in northern Kentucky!

We got there just in time for lunch, so I had a delicious vegetarian ‘cheesesteak’, and Matt got chili, as you do in Cincinnati. Plus Andy Dalton made it, I think.

The rest of our travels were uneventful, and we managed to get the in-laws and all our souvenirs home in one piece!