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Ms. S&C goes southernmost

It has been a month since Ms. S&C returned from her Key West vacay, and she has finally gotten her act together to write a recap of her trip. This was not Ms. S&C’s first visit to the keys. It was her third, actually. Trip number one was Spring Break, sophomore year in college. Trip two was Spring Break, senior year. Trip three was with Mr. S&C, who’s never been there. It is safe to say this visit was different than the first two — but not that different.

People of all kinds visit Key West. Bikers, gays, hippies, retirees, frat boys, the girls-who-love-frat-boys, couples. And many of them visit with one thing in common — drinking. There may be some people-watching and site-seeing, conch fritters and key lime pie, but there is an awful lot of drinking. This heavy-imbibing eclectic mix reminds me a lot of New Orleans. You can call Duval Street the southernmost Bourbon Street.


Ms. S&C had no choice but get used to drinking out of
plastic cups when in Key West

One thing that made this visit different from others: planning. When planning a trip, to Key West, or any other destination for that matter, Ms. S&C recommends you check out the usual suspects for travel ideas: the New York Times’ 36 Hours covers Key West; the Washington Post has several articles; and OpenTable helps with restaurant recommendations. Even with all these resources, nothing beats recommendations from friends (thanks, LC). And with that, Ms. S&C brings you her Guide to Key West.

(Note: Items with an * indicates that I recommend. Items with an * and in bold are the spots I highly recommend, and are the places I would 100% visit again. That means, you shouldn’t miss them if you find yourself there.)


Flew from D.C. to Miami (we got a really cheap flight–$325 for two, round-trip tickets).

Rented a car (splurged on a convertible b/c of cheap flight), and drove down Route 1.  The drive takes longer than you think because you can only go about 40 mph. But, I drove from Virginia my previous two visits, so this 3 and a 1/2 hour trip was a breeze.

Checked in at Island City House*. This is a lovely, affordable inn with gorgeous gardens and a friendly staff. It has a nice pool, serves breakfast, and is an easy walk to Duval Street (and everywhere else). But, it is also far enough way that you escape the constant party-goers.

Swam a few laps in the pool, drank a few Red Stripes (I can’t resit the Jamaican lager when I’m someplace beachy), then hit the town.

Dinner at Seven Fish* – a tiny intimate spot that is a favorite of locals. Probably because it feels far away from the rowdy crowds of Duval Street. There’s a lot of fresh fish on the menu, and the dishes are well prepared. The key lime cheesecake should not be passed up.

801 Bourbon Bar – literally ran in this bar because of an unexpected thunderstorm. I’m sure I’ll see a drag show sometime in my life, but I wasn’t feeling it my first night in Key West. The show is apparently quite good, and the bar itself is fun with great dance music, but I wanted to be out on the town.

Green Parrot* – when googling “jukebox bars + Key West,” the Green Parrot was the top result. Mr. and Ms. S&C love bars with jukeboxes. This jukebox was good, but far too specialized with too much blues and jazz. The place also appears to have a loyal following of locals, again, probably because it is a few blocks off Duval.


Lunch at B.O.’s Fish Wagon* – this can’t be described any other way than an open-air shack. I was a little bit intimidated by the lady-with-a-big-personality taking our order, but the food is definitely worth it. Try the grilled fish sandwich and share an order of fries.

Toured the Hemingway House* – you should take the guided tour (our tour guide was a hoot). You’ll learn about Hemingway, his family, his cats, his work, the house (great architecture and art), and some Key West history. The house itself, and the pool, are amazing by the way.

Captain Tony’s Saloon* – known as the original Sloppy Joe’s and favorite bar of Ernest Hemingway. Not sure he would enjoy it as much today, but it is a great place for people-watching (saw a guy dressed as a pirate, with a live parrot on his shoulder). There’s a mixture of tourists and townies, and maybe a few people who drink for a living. There’s also a really fun (and talented) acoustic guitarist who plays a few days a week. Then, there’s the Pirates Punch, of course.


Pirates Punch is a secret blend of Cockspur rum, gin and a tropical fruit mixture. Served in a souvenir cup that’s yours to keep.

Kelly’s Caribbean Bar and Grill* – Kelly, as in Kelly McGillis of Top Gun, has a casual, yet elegant eatery, with killer happy hour specials—three drinks for $8. Great margaritas.

Green Parrot, again.

Virgilio’s* – recommended by a local we met at Green Parrot. We skipped the martinis (a specialty) and dined on carpaccio, insalata mista and penne puttanesca. Waitress told us we could take our leftover wine “to go,” but we told her we couldn’t.

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