Earlier this year, we made a return trip to Key West. Besides being within a day’s driving distance, we knew that most things to do are outside. At the time, we were still being careful and this was before Florida’s spike in COVID cases due to Delta. I wrote at the time that there seemed to be two groups visiting Key West. Those who were vaccinated and enjoying things they missed and those who only cared about being able to drink a beer without having to remove their mask, who we now know were probably unvaccinated.
When we were there, we ate all of our meals outside. Unfortunately, that eliminated some of our seven favorite places to eat in Key West from the list for this trip.
We did get to revisit several places but skipped our visits to Starbucks because the Kimpton Ridley House gave us breakfast where we could get our morning coffee fix.
On our first night in town, we arrived in time to unpack and walk to Mallory Square and see the sunset.
From there, we needed to find a place for dinner. We walked around the waterfront a bit but everywhere we visited was packed. We came upon a place we’d visited years ago for breakfast and weren’t impressed. However, they had outdoor seating on the patio and no wait. Why not give it another try for dinner.
806 Caroline Street
Key West, Florida 33040
Established in 1909, it’s the oldest restaurant operating in Key West. The restaurant is famous for breakfast and its 1/2 price oysters during happy hour, but we were hungry and wanted dinner.
Another thing Pepe’s is known for is its drinks. The menu is limited but there’s a full bar with premium liquor, unlike the cheap stuff served by the bucket at many other Key West establishments.
I got a basic gin martini and Sharon ordered a classic Hemingway daiquiri. It’s so nice to find a bartender that knows a real daiquiri isn’t a frozen strawberry slushie with rum.
We wanted to get to dinner but I’m not one to pass up a place that’s known for oysters. At least I know they serve enough of them that the inventory is going to be fresh. I ordered a baked 1/2 dozen medley including Florentine, Mexican Roast and Rudi style. I ate two of them before I remembered I was supposed to be taking pictures of the food.
Then it was time for dinner.
I ordered the caesar salad with chicken, which was a huge portion.
Sharon ordered the fresh fish prepared broiled with asparagus and coleslaw. It’s Florida so I’m pretty sure it was grouper but I can’t be 100% sure.
All of our food was fresh so they didn’t have to fancy it up too much. Exactly what you’d expect from a place that looks like a shack from the outside. We were sufficiently impressed that we’d gladly eat here again. We were mad that our first experience was so unmemorable that we’ve avoided coming back for over a decade.
The following day Sharon woke up early and went deep-sea fishing while I stayed at the hotel. Around noon, I got hungry and headed to a Key West spot that’s been on my radar for a while.
B.O.’s Fish Wagon
801 Caroline St.
Key West, FL
Sharon’s generally adverse to visiting food trucks and dive bars. This place is a bit of both. What started as a wagon on Duval St. is now a bohemian paradise located in the corner of a municipal parking lot.
You walk up to the counter and place your order. Grab a seat and wait for your food. The specialty is fish, either grilled or fried with the option of a sandwich or a platter. I ordered a fried grouper platter with fries and a Stella.
When I posted this to my Facebook, Sharon asked where I was and how come I never took her. She’s more willing to eat from a truck in a parking lot than I knew. We’ll definitely be stopping here again.
For our other meals, we went back to some of our favorites.
Nine One Five
915 Duval St.
Key West, Florida
We got there early and snagged a seat on the upper balcony.
The specialty drinks here are incredible. I ordered the Cool as a Cucumber, and Sharon got the Havana Daiquiri.
For dinner, I ordered the Diver Scallops.
Sharon ordered the Crispy Fried Whole Yellowtail Snapper.
She also added a side of the Absurdly Addictive Asparagus.
Nine One Five is one of our favorite restaurants anywhere, not just in Key West.
Finally, we also visited our favorite breakfast place.
530 Simonton St.
Key West, Florida
We knew from past visits that they have outdoor seating in front of the restaurant. I was sad to hear that the duck bacon they used to serve is unavailable due to COVID supply chain issues.
Still, this is one good-looking breakfast.
I can’t think of that many positive things about COVID. However, I admit that we did find some new favorites when forced to try new places.
We’re going to visit Pepe’s and B.O.’s Fish Wagon when we make our next trip to Key West, and that’s something positive.
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This post first appeared on Your Mileage May Vary