Cowboy Mark’s Guide to Key West
Former New York City ex-pat Cowboy Mark shares his favorite spots for drinking, eating, sailing and getting weird in Key West.
Chill or rage?
The Porch & The Other Side
The Porch is a craft beer and wine joint that loosely has a sci-fi nerd theme, while The Other Side is a “fancy” craft cocktail bar.
Both are located in the historic (haunted) Porter Mansion.
429 Caroline St. | 305-517-6358
Best spot to watch people getting thrown out of a strip club while smoking a cigar and drinking port:
The Cork and Stogie
Located on “the quiet side” of Duval St. Boasts 62 different beers both American Craft and Old World and a slew of wines (by the glass and bottle) as well as a modest, but well curated cigar selection.
1218 Duval St. | 305-517-6419
Watch the sunrise? I can’t the floor is in the way!
Don’s Place aka Million Dollar Bar
Dive of dives. Indoor portion has darts, pool and is heavy on the Bud Lite neon. Wander out to the outside portion and you can play The Stooges/Black Flag/Pouges/Taylor Swift on the jukebox while playing a pick up game of corn hole. $3 Rouge Dead Guy!
1000 Truman Ave. | 305-296-8837
Why not practice some free love and freak out?
The Green Parrot
Live music most of the time. Heavy on the NOLA funk, jammy kind of stuff… the occasional blue grass and country acts, and a monthly Uke Jam — a ukulele jam for beginners and pros alike. Cheap PBR tall boys. Popular with tourists and locals.
601 Whitehead St. | 305-294-6133
Practice the ancient Japanese art of karaoke in a gay dive bar:
Bobby’s Monkey Bar
Where the locals hang and belt out the jams. A safe zone for the LGBT community, as well as being epically straight friendly.
900 Simonton St. | 305-294-2655
Free bacon happy hour:
Neo-Classical Americana fare. Gastropub vibe. Call it what you will but this place has a touch of New York and a lil bit Mid Western all at the same time. Sick burgers and killer house made bacon wrapped jalapeño poppers as well as a fish special of the day and a taco of the day. Free bacon happy hour and you roll the dice to see what you pay for your drinks.
416 Applerouth Ln (next to Leather Masters) | 305-414-8626
Sickest, most authentic steamed pork bun:
Best pho on the island. Hang over cures abound. Carbs and spice! Steamed buns are killer. Great sake selection, but get a “can of fun” to go.
601 Duval #4 (enter on Southard) | (305) 296-2077
Best place to score a killer burrito:
Bad Boy Burrito
Verde sauce is legit. Fish taco catch of the day is always a solid choice, or for those more health concerned, get the raw “Power Crunch” salad.
1128 Simonton St | 305-292-2697
Best place to detox after day drinking/drinking all day/night:
Best juices made to order, smoothies, supplements, raw chocolate and great coffee. The breakfast wrap is top notch and for the vegans — a French toast to die for.
829 Flemming St. | 305.296.7766
OTHER FUN STUFF
Left your butt plug at home?
Yep. It’s a leather and sex shop. Get all your butt plugs and BDSM gear here or maybe just some furry handcuffs.
418 Applerouth Ln. | 305-292-5051
Go on an adventure:
Take a class and learn how to make your own skateboard, pick up some vintage-inspired foul weather gear or a hand crafted surfboard, commission a boat to be built, or see a surf band (local faves Patrick and the Swayzees play late night). Slick t-shirt design by Brooklyn’s Duke Riley too!
6404 Front St. Stock Island
Keep it KVLT:
Key West Cemetery
This cemetery boasts some of the funniest head stones ever like “I told you I was sick!”, along with a stone statue of a woman sitting on a mans face. The remains of the fallen sailors of the U.S.S. Maine also rest here (the incident sparked the Spanish-American war). Fun fact: Key West was once called “Cayo Hueso” by the Spanish which translates to “Bone Island.”
Feel the burn:
Old Town Fitness
Watch Navy Seals & Army Rangers do superman push-ups while you bench press 100 lbs.
1010 Truman Ave (next to Don’s Place) | 305-292-3999
Watch the sunset while getting trashed in a wine class:
Danger Charters "Wind and Wine Tour”
Sunset is a huge thing here. It’s epic. Also we like to drink a lot. The lovely folks at Danger Charters had the foresight to put the two of KDubs fav attractions together. They also offer “eco” adventures and other various trips.
Best schooner in the fleet:
This historic lady does daily voyages out of the Key West Bight. It’s a romantic trip back in time. Sick sunset trips!
211 Williams Street | C-Dock at Margaret St | 305-509-1771
After many years as a downtown DJ in NYC, Cowboy Mark moved to the sunny shores of Key West. Luckily, he still comes to visit NYC from time to time!