Key West 2023

Friday

This trip we were traveling with our friends, E and Stacey. It was their first trip to the Keys, so I was a little nervous. Would they love Key West as much as we did?

Our plane got into EYW at 2:30. We made a quick run to Publix for essentials (beer and half-and-half for coffee), dropped our luggage off at Chris’s house on Grinnell Street and headed to the Historic Seaport. I thought the waterfront would be a good place to introduce E and Stacey to Key West. It was St Patrick’s Day, so the people-watching around the seaport was even better than usual – lots of green beads, green bras, elf shoes, tutus, you name it. We even saw one guy dressed as St Patrick in green robes, a bishop’s hat and a staff with a snake wrapped around it. I think we saw more people walking with their dogs than usual too, but maybe I just noticed them more because E and Stacey were missing their dog, Bristol, so we stopped to say hello to all the “puppers”. It didn’t matter what size the dogs were, they were all puppers. :-)

We found an outdoor table at the Boat House, which had great Happy Hour prices – 50% off small plates, beer and well drinks. Even the mojitos were half price! I had my first mojito of the trip, and Ron and I shared a plate of chicken wings. Stacey ordered something called “boat bread with chef’s toppings” and it was delicious. We’ll definitely have to go back to the Boat House on our next trip.

When we were done with our appetizers, we meandered towards Mallory Square. The weather forecast had been calling for rain all weekend, so we thought it was probably our best chance to see the sunset celebration. You can’t go to Key West without seeing at least one sunset! When we got to the square, I noticed a man with a curly gray mullet. Was that the Catman?? It was! Dominique LeFort, aka the Catman, was a fixture at Mallory Square for decades with his famous flying cats. He and his cats were getting older, so he’d decided to retire when COVID hit, but he’d been promising to return for another show “in two weeks” for the last two years. I said hello and talked to him for a bit. He was very gracious and friendly.

We found a spot to sit on the seawall with our legs dangling over the water, watching the sailboats passing back and forth. It was a pretty Key West sunset, but I realized later that we should have walked further down towards the entertainment to give E and Stacey the full Mallory Square experience. Ah well… You can never fully experience a place in one visit. I guess that gives you an excuse to go back.

After the sunset, we had dinner at Garbo’s Grill, the food truck behind Hank's Hair of the Dog Saloon. The guys shared the Korean BBQ tacos, and Stacey and I shared the shrimp tacos. We walked back to the house by way of Duval Street, which was busy but not nearly as crowded and crazy as it was two years ago. It was a long walk and by the time we got back to the house, we were ready to get off our feet and crash for the night.

Saturday

Saturday was our day to check some of the “first timer must-do” items off our list. We’d rented bikes from Eaton Bikes, and after all the walking we’d done the day before, we were happy to be riding. You can see so much more of Key West on a bike. We started with the Southernmost Point Buoy, where we stood in line for 20 minutes for the obligatory picture. Then we rode to the Hemingway Home and Museum. We bought tickets for the museum but skipped the guided tour and walked around on our own. Ron and I had seen the house before, so I mostly spent time looking for the Hemingway cats. There are 50-some cats at the Hemingway Home, so I didn’t have to look very hard. There was even one sleeping in a flower pot by the pool. :-)  The cats are descendants of Ernest Hemingway’s six-toed cat, Snow White, and although not all of them have extra toes, they all carry the gene.

the Southernmost House

Hemingway Home

Babe Ruth, one of the many Hemingway cats

It was late morning and we were getting thirsty, so we pedaled on to Captain Tony’s Saloon, the historic bar where Hemingway spent a lot of time in the 30’s and Jimmy Buffet got his start in the 70’s. The bar stools at Captain Tony’s were painted with the names of famous people who had spent time at the bar. We saw Dan Marino, John Goodman, Dale Jr, Sean Connery and Shel Silverstein. (I didn’t know until recently that Shel Silverstein had lived in Key West.) Our bartender told us that Robert De Niro came to the bar every night for a week to earn his stool.

Then it was back to Garbo’s Grill for lunch. I branched out from my usual tacos and tried the Mango Dog, which was amazing, a quarter-pound hot dog topped with mango and jalapeno. Yum! Sheldon Benton, the young musician we’d heard at Hank's Saloon on our last trip, was playing again. We listened for a while, then went across the street to First Flight and sat at the bar, chatting with a hilarious family from New Jersey. Ron and I shared a plate of the Brussels sprouts. That's one thing about Key West - you can eat well just grazing on appetizers and Happy Hour specials. We did a lot of grazing. :-)

Garbo's Grill

First Flight

The forecasted rain hadn’t materialized yet, and it was sunny and hot. We pedaled back to the house and spent the afternoon relaxing by the pool. For dinner, we headed down to the Conch Republic Seafood Company at the seaport where we found a table on the outdoor deck. I decided to try their Royal Red shrimp, which are supposed to be sweeter than other Gulf shrimp, more like lobster. They aren’t on the menu, but I’d read on Trip Advisor that you can request them. My Royal Reds really did taste like baby lobster tails, but E’s blackened shrimp was overcooked and only blackened on one side. E mentioned the one-sided seasoning to our waiter, who gave us some free drink tokens to use the next day. We were all tired, so we rode back to the house and sat out on the porch, talking into the night.

Sunday

The next morning, Ron and I continued our tradition of trying a new breakfast place whenever we’re in Key West. This time we chose Pepe’s Café, the second oldest eatery in Florida (after the Columbia in Tampa). It had been operating since 1909 and was frequented by President Truman, who would stop by for coffee. The ambiance was rustic, the portions were large. The sunny weather had given way to clouds, but it was cooler and pleasant as we rode back to the house to meet up with E and Stacey.

We didn’t have any particular plans for the day except to look for a funny Key West sign for our friend Joe’s garage sign collection. We popped into a few of the shops along Duval Street and ended up at Mallory Square, where we explored the memorial sculpture garden. Mallory Square was surprisingly quiet considering it was “tourist central” and a cruise ship was in port. We found seats at a little bar called Salty Frog’s and chatted with the bartender. He was from Nashville but came down every month or so to help his friend who owned the bar. A very cool guy. While we nursed our drinks, we took pictures of the roosters and baby chicks. They were everywhere! E said that he didn’t think he’d get used to hearing roosters all the time, but I didn't mind. Just like the tree frogs in Jamaica at night, I know I’m on vacation when I hear the roosters.

Mallory Square

Key West Memorial Sculpture Garden

El Meson de Pepe

At around 3, we rode to Conch Republic Seafood to use our free drink tokens. That’s when we realized that the tokens were only good during Happy Hour. And the bartender was RUDE. Someone had hooked up the beer taps wrong, so instead of Bud Lite, E and Stacey ended up with a weird Key lime beer. The staff switched out the kegs but didn’t clear the lines. When we told the bartender that the beer still didn’t taste right, she said shortly, “It tastes fine to me!” What a contrast to the great bartender at Salty Frog’s. Usually we like going to the Conch Republic, but this trip it was very disappointing. Plus, they had added an annoying 3% surcharge unless you paid in cash. It wasn’t that long ago that a lot of places wouldn’t even take cash!

That night we had dinner in the cozy little courtyard at Mangia Mangia, one of my favorite places. The fresh homemade pasta was as delicious as always. It was our last night, so we decided we needed to hit a couple more bars before we had to go home. We just couldn’t decide which bars. So many choices, so little time! I really didn’t care where we went as long as they had mojitos and live music. :-)  We ended up back at Captain Tony’s. While we were pulling some barstools together, E fell over the roots of the big tree growing through the roof of the bar. Legend has it that the tree was used to hang pirates, so we teased E that the ghosts of the pirates had tried to trip him. After Captain Tony’s, we went to Sloppy Joe’s. Yes, it's touristy, but it’s something every first timer must do. My mojito was surprisingly good. It was made with Papa’s Pilar rum, a local rum named after Hemingway’s fishing boat, Pilar. I thought we’d been able to give E and Stacey a pretty good overview of Key West in a short time - a sunset at Mallory Square, the seaport and Southernmost Point, iconic bars, good food, a little history, a lot of chickens.

Mangia Mangia

On the walk back to where we’d parked the bikes, we passed a sweet shop that had amazing-looking gigantic cookies in the window. Suddenly, we all had a craving for milk and cookies. We bought three cookies and picked up half a gallon of milk from the CVS across the street. Halfway home, the rain and wind finally arrived, and we got pelted. When we got to the house, we divided up the cookies four ways and ate them outside under the shelter of the gazebo before going to bed.

I woke up at 2:30 to the sound of pouring rain and the palms whipping in the wind. Thank goodness it hadn’t rained like that all weekend! We were very lucky with the weather.

Monday

By the time we were up in the morning, the rain had stopped and the clouds were breaking up, but it was still crazy windy. We had some time to kill before our flight, so we took a walk around the Key West Cemetery. Before the trip, I’d bought a quirky guidebook called The New Key West Bucket List that included over a hundred “offbeat adventures”.  The legality of some of the activities were a bit questionable, but I liked the Did You Know facts, such as this one: “The law forbids people who live in houses on the perimeter of the Key West Cemetery from being buried there. This is because they are not yet dead.” :-)

We checked out an intriguing monument that we’d noticed when we’d biked by on Saturday. It was shaped like a giant conch shell (or possibly a body part). The conch shell turned out to be the final resting place of Sir Peter Anderson, the Secretary General of the Conch Republic. His inscription said simply, “He had fun.” And so did we! Long live the Conch Republic!

Key West Cemetery

Mojito Review

I had so many mojitos this trip that it was hard to rank them. Instead, I’ve broken them up into categories.

The Best:

• •  El Meson de Pepe – always at the top of my list
• •  Sloppy Joe’s – made with Papa’s Pilar rum and lots of fresh mint
• •  Boathouse – half price for Happy Hour!

The Good:

• •  Hank’s Hair of the Dog – just a hint of citrus flavoring
• •  Captain Tony’s Saloon – a good balance of rum, lime and club soda
• •  Conch Republic Seafood Company (blackberry mojito) – although I usually stick with classic mojitos, I liked the slightly tart taste of the muddled blackberries

The Ugly:

• •  Mallory Square drink cart – The only mojito I didn't finish. The mint was completely disintegrated.