MY KEY WEST
Having been visiting Key West since 1984, and having lived there for six wonderful months in 1995, I am often asked for travel tips to the Conch Republic. This listicle is for tourists visiting Key West for the first time, or for locals and regulars, who are always looking for hidden gems.
On Your Way Down and Back
The Drive from Miami to Key West is just over three hours, so its sometimes nice to take in a stop or two on the way. Here are a few highlights:
58000 Card Sound Rd, Key Largo, FL 33030
Dive-y biker bar, but with a strange, almost Acadian local presence. Have drinks and seafood on the canal, while sometimes a Cajun band plays for line dancers in ethnic period wardrobe. Moderately surreal.
95710 Overseas Hwy, Key Largo, FL 33037
Amazing breakfast place, a perfect distance away from Miami to lay a foundation for an afternoon in Key West. Famous for its baked goods. Biscuits and gravy are amazing, and you must get blueberry muffins.
Lorelei Restaurant & Cabana Bar
96 Madeira Rd, Islamorada, FL 33036
Great lunch and sunset happy hour. Live music at night. Super low-key (but nice) waterfront location.
30813 Watson Blvd, Big Pine Key, FL 33043
Still 45 minutes out of Key West, need to take a stop? This gem has great food, drinks and atmosphere.
Hotels in Key West are obviously all expensive in season, so you might as well stay somewhere nice, and in walking distance of Old Town — basically the northwestern triangle from the Southernmost Point marker, to Mallory Square, to the Half Shell Raw Bar. There are tons of mid-price hotels in this area, almost all are acceptable to all but the extremely snobby.
1015 Fleming St, Key West, FL 33040
This is my go-to place. I’ve been going there for years. Comfortable tropical vibe. Happy hour at the pool is always fun.
1 Duval St, Naval Air Station Key West, FL 33040
Very she-she and resort-y, but right there in the middle of it all. Top flight.
412 Frances St, Naval Air Station Key West, FL 33040
Probably the best B&B on the rock.
1500 Reynolds St, Naval Air Station Key West, FL 33040
A historic Henry Flagler hotel, done up right. It is far enough away from the din on Duval Street to feel like you’re really on vacation, and close enough to get back safely after a night out.
Breakfast in Key West is on island time. In some places it is served all day. Wherever you go, check before you go to make sure you don’t miss the switch to the lunch menu.
806 Caroline St, Key West, FL 33040
A local favorite, which harkens back to Key West’s Cuban roots. Food’s good, atmosphere is great.
729 Thomas St, Key West, FL 33040
This is the iconic Key West spot, it is always crowded. Those in the know learn to put your name in with the host, and have a few bloodies at the bar while you wait for your table. In season they usually have live music. Located in the Bahamian Village, featured are the free-roaming chicken and cocks.
Bars and Restaurants
Drinking and eating are the primary activities in Key West, which makes it an ideal adult playground. The locus of the bar scene is the north part of Duval Street, and while there are many fine places there, most cater to tourists, which means you get the same crowd of louses, drinking the same Michelob Lite Ultras, listening to the same Jimmy Buffet wanna-bees playing the same gee-aren’t-we-having-fun-now songs. My inclinations are to places where locals go, which usually have more interesting people, better entertainment, and cheaper drinks. Among those, these are some of my favorites:
202 William St, Key West, FL 33040
This place is truly the heart of Key West. Cheap drinks, great food, quirky wait and bar staff, and there is always live music, including the local legend Michael McCloud, who will sell you a CD for any price you set (“If you haven’t taken advantage of anyone yet today, let me be the first”).
511 Greene St, Key West, FL 33040
Great sports bar, dozens of screens. If you want a table or a seat at the bar on an NFL Sunday, though, you better get there early.
400 Front St, Key West, FL 33040
Best live music in Key West. Good raw bar, great atmosphere. Gets crowded after sunset when the Mallory Square crowd wanders back into town.
201 Duval St, Key West, FL 33040
Yes, it’s a tourist bar, but it’s the tourist bar. A must stop, even if to take in the atmosphere, and imagine Hemingway pulling up a seat next to you.
224 Duval St, Key West, FL 33040
This is the dark horse pick. Most people hate the place. It does suffer from a sort of trashy vibe, but the architecture is amazing, the drinks are cheap, and window table will give you the best people watching in town.
524 Duval St, Key West, FL 33040
The address is listed as Duval Street, but the entrance is on the north side of Appelrouth Lane, which is probably the coolest street in Key West. Advertised as a martini bar, it is still nominally a gay bar, but in typical Key West fashion, straight people are always welcome. Great small combo live music, cool local crowd.
821 Duval St, Key West, FL 33040
The place to go if you want some upscale atmosphere, far enough away from the loud, drunken tourists to catch a breath and relax. Food, drinks and music here are all top shelf, great local crowd.
601 Whitehead St, Key West, FL 33040
Yet another icon. No pub crawl is complete without a stop here. Great bands, super jukebox, cheap drinks, and a crowd of mostly locals and island regulars. Ask a bartender about the story behind Smirk.
501 Southard St, Key West, FL 33040
No night out is complete without some greasy food that will moderate the effects of perhaps a few too many drinks. This place has the choicest cheesesteaks and some pretty decent pizza, and it’s a stone’s throw from the Green Parrot.