Key West…what a fun city! It definitely has a distinct, almost-Bohemian feel to it. The little sister to New Orleans comes to mind when I try and best describe it. Chickens and roosters roam the streets and restaurants as if they own the town. Fishermen clean mahi mahi next to their boats in the Galleon marina just five feet from restaurants blackening these same mahi mahi on the grill. Tourist cruises and motoring tiki bar boats fly in and out of the marina what feels like every hour. Scooters and bike riders dominate the streets while the main artery of the city, Duval street, booms with vendors and walking tourists. The locals alone are one of the coolest aspects of this city. They are to-the-point, rough around edges, serve it to you with a smile and backhand-type of crowd. Their dry sarcasm was right up my alley.
I boated to Key West with my husband and in-laws from Marco Island, Florida. We docked in Tavernier, Florida for a few days then were ready to explore what seems to be the heart of the Florida Keys, Key West. En route to Key West, my husband and I scoured the internet for some of the best places to eat and things to do while in Key West. As we wrote down a few key restaurants we thought sounded good, we quickly realized that most restaurants had great reviews and it was hard to come by a menu that didn’t sound delicious. We said “screw it”, let’s just explore and see what happens.
We docked in the Galleon marina and set off on our adventure. Not before our usual ranking of all the boats around us in the marina of course. Here are some of the best food and tour recommendations I can give from our short time here in Key West. We just skimmed the surface of Key West so keep in mind this is a small piece of the (Key Lime) pie (sorry couldn’t resist) when it comes to things to eat/do/see. I can’t wait to go back and do a deeper dive but for now, here’s a small taste of the great things we experienced in Key West.
Best Food:
- Breakfast:
- Blue Heaven. This restaurant by-far had the most interesting history. Restaurant tables are nooked back in a little courtyard under a huge almond tree that spans the blue sky as far as your sight can take you. The property where the tables sit was once home to long nights of gambling, cock fights, and boxing matches refereed by no other than Ernest Hemingway himself. The rich history is visceral in the outdoor seating section. Food recommendations: Veggie Benedict, Ham Benedict. Also, you won’t want to miss the incredible Key Lime Pie here. The meringue towers about six inches above the pie itself. If any of you have ever tried to make a meringue in your free time understand what a true artform that is.
- Blue Heaven. This restaurant by-far had the most interesting history. Restaurant tables are nooked back in a little courtyard under a huge almond tree that spans the blue sky as far as your sight can take you. The property where the tables sit was once home to long nights of gambling, cock fights, and boxing matches refereed by no other than Ernest Hemingway himself. The rich history is visceral in the outdoor seating section. Food recommendations: Veggie Benedict, Ham Benedict. Also, you won’t want to miss the incredible Key Lime Pie here. The meringue towers about six inches above the pie itself. If any of you have ever tried to make a meringue in your free time understand what a true artform that is.
- Casual Lunch/Dinner:
- Schooner Wharf Bar. Our first stop of the trip. This bar had all the feels of Key West and from what we heard from the locals, it truly DOES fit one of the best descriptions of old Key West. Complete outdoor restaurant and bar with so many umbrellas and canopies you feel a slight relief from the stifling August heat. Gravel floors, chickens and roosters roaming and eating food scraps wherever they can find them, live music, and really great food. I mean really good. Our food favorites: Snapper/Mahi-Mahi Sandwich Melt, Mayan quesadilla with shrimp, and the fish taco wrap. This food paired with the Lizarita margarita started our trip off perfectly, but I may be bias.
- Conch Republic Seafood Company. This place took me by surprise. Nothing special about it when you look at it. Typical Key West outdoor bar and restaurant with live music looking over the marina. But it really snuck up on us. Went in with little expectations and left wanting more. And don’t worry, we got more 😉 To top it off, the service here was always on point. Whether you sit at the bar or in the restaurant, staff was very attentive and rather fast for always being packed. Enjoying the live music with a Corona in hand and a misting fan to keep me cool, what’s not to love? Did I mention it sits next to the marina? The fishing boats dock about five feet from the restaurant and filet the fish you’re about to eat right on the dock. Our food favorites: oysters on the half, conch chowder, island salad with seared rare tuna, local fresh catch of the day sandwich, blackened jumbo scallops, stuffed shrimp, island salad with seared tuna.
- Schooner Wharf Bar. Our first stop of the trip. This bar had all the feels of Key West and from what we heard from the locals, it truly DOES fit one of the best descriptions of old Key West. Complete outdoor restaurant and bar with so many umbrellas and canopies you feel a slight relief from the stifling August heat. Gravel floors, chickens and roosters roaming and eating food scraps wherever they can find them, live music, and really great food. I mean really good. Our food favorites: Snapper/Mahi-Mahi Sandwich Melt, Mayan quesadilla with shrimp, and the fish taco wrap. This food paired with the Lizarita margarita started our trip off perfectly, but I may be bias.
- Surf & Turf:
- A & B Lobster House. If you’ve had your fair share of seafood and craving a nice, juicy steak, this place is for you. It’s just an extra bonus that they also have great seafood. The environment is a little fancier than the other restaurants on the historic boardwalk, but you’ll see every walk of life here so don’t worry too much. But do everyone a favor, take a shower, and put on your nicest Key West attire for this white tablecloth, candle-lit dinner. Can’t go wrong here, especially if you fancy yourself a night cap. The old cigar lounge and bar adjacent to the dining room makes a mean martini and will give you all the historic feels. Food recommendations: New England clam chowder, butter-poached Florida lobster tail, 2lb main lobster bake, filet mignon, and ribeye.
- Cocktail by the water:
- Sunset Tiki Bar by the Galleon Resort. Off the beaten path of the main boardwalk. A great spot to feel the salty breeze in your hair while overlooking boats come and go. The mango daiquiri and piña coladas here come with a kick-in-the-pants topper that will really get your day going 😉
- Sunset Tiki Bar by the Galleon Resort. Off the beaten path of the main boardwalk. A great spot to feel the salty breeze in your hair while overlooking boats come and go. The mango daiquiri and piña coladas here come with a kick-in-the-pants topper that will really get your day going 😉
Places/things to see:
- By foot:
- Duval street: The hustle and bustle of Duval street is reminiscent of Bourbon street in New Orleans, but less sloppy (unless of course, you are stumbling out of Sloppy Joe’s bar). This historic street is the main artery of the city with plenty of great restaurants, bars, shopping, and art galleries to be seen here. You can easily spend a full day wandering up and down this street while munching on macarons and slurping a Corona Light…well at least that’s what I did. To each their own.
- Historic Harbor Walk: If you’re sober enough to wander beyond Duval street, this is where you’ll want to go. This historic boardwalk lines multiple marinas and some of the best seafood and live music in the city (some of the places are mentioned above-A&B Lobster House, Conch Republic, Sunset Tiki Bar, Schooner Wharf Bar, etc.). From here, you can also take several different tours (sunset cruises, snorkeling adventures, fishing charters, Dry Tortugas day tours, etc.). Wandering along this harbor walk, you’re also likely to see fisherman fileting their fresh catch of the day, massive tarpon circling in the water for their 4pm tourist feeding, and if you’re lucky like I am, a shark 😉
- Duval street: The hustle and bustle of Duval street is reminiscent of Bourbon street in New Orleans, but less sloppy (unless of course, you are stumbling out of Sloppy Joe’s bar). This historic street is the main artery of the city with plenty of great restaurants, bars, shopping, and art galleries to be seen here. You can easily spend a full day wandering up and down this street while munching on macarons and slurping a Corona Light…well at least that’s what I did. To each their own.
- By scooter or bike:
- Ernest Hemingway House and Museam: This historic landmark was home to the famous author and manwhore (if I do say so myself; no insults, just factual), Ernest Hemingway. This beautiful home hosts several daily tours and private events, while also housing more than 40 cats with six toes. These cats are protected, treated like royalty and roam the grounds as such. I would too…this house is stunning and jam-packed with interesting history that speaks volumes of Ernest Hemingway and Key West as a whole.
Polydactyl cat (six toes) - Key West Lighthouse Museum: You might want to make sure you hold off on the drinking before going here. The 1000+ winding steps (just kidding, it was only 88 steps but my god, it felt like a 1000) to get to the top of the lighthouse might make you feel a little woozy, but it’s definitely worth the view. From the top, the lighthouse points out historic landmarks so you know what you’re looking at. Another really great thing for those who haven’t done their research (cough, cough: me). Bonus: the keeper’s quarters offers a great air-conditioned reprieve from the scorching August heat. Oh yes! Back to the history. In all seriousness, the actual historical lights that were once used in the lighthouses, in addition to the countless other nautical artifacts make this spot worth the trip.
- Key West Garden Club: Need a serene getaway from those that you’re traveling with? I’ve got your back. This old army fort is chalk full of beautiful blossoming flowers, trees, butterflies, and shrubs. This tranquil spot has some of the best views in Key West. It yields that looking-out-of-a-treehouse-onto-the-ocean-type-feel, similar to how I think I would have felt if I lived with the Swiss Family Robinsons. In different corners of this vegetated respite are great lookouts onto Higgs Beach (and pier) and Edward B. Knight Pier. Bonus: this is a free tourist location (however donations are welcome).
- Southernmost point: This popular tourist attraction is exactly what it sounds like. It is quite literally the most southern point of the continental U.S. A large buoy now anchored to the ground stands at its point and is home to many tourist pictures. Many people stand in a long line to get a picture while touching the buoy. That wasn’t really our kind of thing so we opted for a bike ride drive-by.
- The outskirts of the island: One of my favorite things we did was rent a scooter and drive around the outskirts of town. Here you get a real lay of the land and in my case, a true understanding of which way is Cuba and which way is mainland Florida. It’s difficult for some of us. A little wind in the air on a hot day doesn’t feel half bad either, but be careful not to leave a black-seated scooter parked out in the sun for too long. I learned the hard way and burned my ass.
Just kidding. Ours looked like the red one 😉 
- Key West cemetery: Everyone loves an above-ground cemetery. You don’t get to see these just anywhere, at least not in Michigan. It’s an easy scooter drive-by or feel free to take your time and explore. Just don’t stay after nightfall.
- Ernest Hemingway House and Museam: This historic landmark was home to the famous author and manwhore (if I do say so myself; no insults, just factual), Ernest Hemingway. This beautiful home hosts several daily tours and private events, while also housing more than 40 cats with six toes. These cats are protected, treated like royalty and roam the grounds as such. I would too…this house is stunning and jam-packed with interesting history that speaks volumes of Ernest Hemingway and Key West as a whole.
- By boat: On our last day in Key West, we took a tender boat ride around the majority of the island. This is one of the best ways to explore the waters around the island.
- Naval Air Station, U.S. Army grounds, Coast Guard boats: If you spend more than 10 minutes in Key West, you quickly realize the heavy U.S. Army and Navy presence here. Helicopters and jets fly over frequently. But there’s a different feel to this when you’re on a boat vs. land…peering above into the blue sky to try and catch these little jets all in formation. Truly American comes to mind.
- Liveaboards and derelict boats: This doesn’t too terribly interesting but imagine the shows tiny houses and hoarders combining…that’s how interesting some liveaboard boats can be. You can spend all day circling these boats trying to figure out how the hell they fit that much stuff onto a boat or what went wrong, in the case of derelict boats left halfway in a tree or half sunk. So many secrets kept by the sea.
- The wildlife! Sharks, sea turtles, jellyfish, dolphins, pelicans, herons…best seen on a boat. Trust me!
- Naval Air Station, U.S. Army grounds, Coast Guard boats: If you spend more than 10 minutes in Key West, you quickly realize the heavy U.S. Army and Navy presence here. Helicopters and jets fly over frequently. But there’s a different feel to this when you’re on a boat vs. land…peering above into the blue sky to try and catch these little jets all in formation. Truly American comes to mind.
That’s all I have for now! If you’ve traveled to Key West, be sure to comment below with your favorite tourist and foodie spots…I would love to hear them!
-EAB