The Keys to Where to Stay, Snack, and Sunset in Key West

January 12, 2023

“Sir,” I said as I stood to catch the waiter, “a chicken just jumped on my salad.”

The waiter calmly came over, smiled, and whisked the plate away, assuring me that a replacement was on its way — this was clearly a common occurrence. From a few feet away, the chicken (technically a rooster) stared me down defiantly.

“Not a chance, buddy, or next time I’ll order the chicken strips,” I said, staring right back.
It was day three in Key West, and we’d learned that these beauties run the town. We were not only prepared to live in harmony with them, but we’d already extended our trip for three more days. I’ve seen Jimmy Buffet in concert way too many times, but his lyrics had never stuck in my head like they did here:

  • “Don’t know the reason, stayed here all season, nothing to show but this brand-new tattoo…” (credit: Margaritaville)
  • “Still time to start a new life in the palm trees…” (credit: Weather is Here, Wish You Were Beautiful – AKA, best song title ever)

These songs exemplify why visitors to Key West tend to extend their trips, first by days, then by weeks. Our first trip back (after about 10 years) was mid-pandemic.  It was cold at home, everyone was working whenever and wherever, so our originally planned four day trip turned into a week.  And now we’ve found ourselves returning every year and trying to describe to others why.

Key West is touristy, especially in some parts like Duval Street, Hemingway’s house, Sloppy Joe’s, and the Southernmost Point. The island is quirky. It’s a bit weird. The restaurants aren’t particularly great (good is a more fair assessment). Key West pinks (which are essentially — don’t let anyone fool you here — shrimp) are considered fine dining, and most of the restaurants boast vibes matching names like the Thirsty Mermaid, Flying Monkeys, and Flaming Buoy.
And there’s not much to do. I mean, sure, there are water sports, bicycling, and fishing… But there’s literally nothing productive to do, hence my guy Jimmy’s line about nothing to show but his brand-new tattoo.
But… it kind of doesn’t matter there. You get up in the morning, throw on a (probably rumpled) T-shirt and shorts, walk out onto your porch/patio/beach into 72-degree weather, and take in a spectacular sunrise. Then you stroll down the street to any one of the over 400 restaurants on this tiny island to get coffee or maybe breakfast. Then, somehow, you’ve filled the day and it’s time for sunset and cocktails. Wake up the next morning and hit repeat.

It’s oddly calming, which for two people who don’t particularly understand “calm,” is revolutionary. There’s a beauty to celebrating a bit of consistency every day, especially when that “consistency” is 79 and sunny, you’re surrounded by water, and every sunrise and sunset is a stunner.  In our most recent trip, we brought friends, and forgot to mention the humidity and consistent temperature from morning to night. So, their luggage filled with long sleeve shirts went to waste.

This is not a Mexico beach vacation, where well-oiled party kids and families spend their days flipping in the sunshine. It’s a place filled with people of all shapes and sizes, on bikes of all shapes and sizes (pick your ride — road, mountain, cruiser bike — from Eaton Bikes), cruising around the island. If you’re so inclined, you can also rent a golf cart on every corner. It has a laid-back, “have a Bloody with breakfast” vibe that makes you realize how unimportant your daily tasks at home can be. It may not be sustainable long-term, but it’s sure fun to hang out with the people who have made it just that.

The cute houses with giant front porches line streets packed with palm trees and are dotted by people sitting on their swings enjoying a book or morning coffee. If you stay away from Duval Street, the avenues are quiet and calm at night, still with an upbeat energy due in no small part to the fact that everyone is smiling, all the time.

If you go:

There are a few hotels off the island that are incredible (Sunset Key Cottages, the island oasis of Little Palm Island), but for the first time, stay somewhere with walking access to explore town: The beauty of Key West is getting immersed in the weird and quirky everyday.

  • Marquesa (especially the new addition, Marquesa 4-1-4) has an in-the-center-of-it-all city vibe with quiet outdoor spaces to enjoy.
  • The Kimpton Hotel group has purchased a number of quirky properties throughout old town, and friends that have stayed there said it’s a great option.
  • Many of the people we met also told us that the local B&B and AirBnB options aren’t overhyped. Key West is not a place where you want to be in a giant resort hotel.
  • Ocean Key is the best “resort” hotel with a good sunset location.  It’s a good option if you like bigger hotels, and want to be on the water.

Restaurants are another thing. This is not a culinary destination, but if you spend too much time on Yelp or TripAdvisor (please, don’t), it may be touted as one. That said, there is good food here.

For breakfast:

  • Blue Heaven is the one thing Trip Advisor gets right. It’s quintessential backyard Key West, and the banana bread and Benedicts of all varieties are very good and the chickens are the entertainment. The Key lime pie is one of the better ones to photograph, but don’t bother actually eating the tower of meringue (just get right to the pie below). It’s also a great choice for dinner; you can’t beat the vibe of a dirt patio and central outdoor bar.
  • Pepe’s makes you feel like a local, and their daily homemade breads make it worth cheating on Keto. Belly up to the bar and they’ll make you feel at home.
  • And a general tip: Get used to a Bloody Mary, mimosa, tequila sunrise, etc. in the morning, maybe before or after your iced coffee or Cuban coffee. Funky Rooster and Cuban Coffee Queen are best if you actually have to be back to your hotel for a 9:00am Zoom call.

For lunch/dinner:

  • Cafe Marquesa and Little Pearl are known as the best in town. They’re both good, and the service at Marquesa is exceptional, but keep in mind that “the best” is relative. Marquesa is definitely worth a visit, but the Little Pearl’s current prix-fixe-only menu becomes too much food over too much time. On our more recent trip, we tried Little Pearl’s Italian sibling, Antonia’s, and it was a solid choice for Italian food (even though it’s on Duval Street).
  • Santiago’s Bodega is one of the few places we returned to and also the home of the now-infamous rooster. The petite rack of lamb, the flaming halloumi cheese, the hummus, the mushroom puff pastries… It was all very good, especially when sitting on their outdoor porch.
  • We consider ourselves certified lobster-roll pros, and the one at Eaton Street Fish Market rivals many we’ve had in Maine.
  • We usually stay away from Duval Street, with two exceptions. Bagatelle is pretty good for brunch, and their outdoor porch seating at the end of Duval is just right. Nine One Five is a fun spot, but head upstairs for a cool little bar and outdoor space that overlooks the action without being right in it.
  • Mangia Mangia is a cool, local, mostly pasta place with yet another great, rustic outdoor dining area.
  • The fish tacos and the key lime cheesecake at Seven Fish were incredible, but, as restaurant designers, we found the space a little distracting.
  • For lunch one day, it’s worth the car or short Uber/Lyft ride to enjoy the vibe at Hogfish Bar on Stock Island.

Additional Keys:

For beach dining, Louie’s Backyard has the best location — especially the “afterdeck” bar which is set right on the water. If you want to eat in the restaurant, be prepared for a wait, but we preferred the afterdeck (put your name on the list and enjoy a cocktail while you wait for a seat). Salute is another good option, right on Higgs Beach, and has good sunset angles. Speaking of sunsets, if you want to play tourist while sipping a cocktail, the go-to spot is Hot Tin Roof in the Ocean Key — but the fight through Mallory Square can be crazy, so cruise through just once to see the spectacle.

On our last trip, we had a great afternoon in the outdoor patio of First Flight, which had surprisingly good, elevated bar food.

For sunsets, the best place to see it and celebrate it (which everyone does) is by boat, and there are a number boats and captains for hire. For sunrises, find a place anywhere from the Southernmost point to Higgs Beach (and if you’re staying at Casa Marina, it’s built in, along with a decent sunset shot). Even better is hopping on a bike right before sunrise and taking it in as you pedal along the route to earn your Benny and your Bloody; there’s no greater way to start the day.

The key lime pie debate is as controversial as politics, so we’re not going there. We’ll just say that our favorites were Kermit’s (sometimes — though rarely — places are famous for good reason), Old Town Bakery, and that Blue Heaven slice sans meringue. The aforementioned key lime cheesecake at Seven Fish was a serious contender for our favorite dessert, though. Apologies to the pie purists.

For great cocktails beyond rum and Coke (or, I’m sorry, a Cuba Libre if we’re keeping it fancy), head to General Horseplay or The Roost. They’re both a bit more inward-facing, but the bartenders are the best, and the drinks are good. The Roost in particular will immediately feel like your neighborhood bar (complete with an exceptional martini), and you’ll meet the many people who came down for four or five days and are still here 25 years later.

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