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.


Um, let’s just say I didn’t feel my best when I woke up. Pirates Punch can do that to you.

Fort Zachary Taylor State Park – took the guided tour of the fort. Wouldn’t necessarily recommend it unless you’re a real history buff. Our tour guide gave us a hard time for “having too much fun” the night before. But it wasn’t our fault his “port noise complaint” joke fell flat. We got the “Portnoy’s Complaint,” reference; it just wasn’t that funny. The park is good for other activities though (bike riding, hiking, swimming).

El Siboney* – really awesome authentic Cuban fare. The conch chowder, even on a hot day, is so good. Its tomato-based and incredible, especially with the basket of buttery bread. You can pass on the Cuban sandwich, and get the pulled pork instead (you must get it — the platter includes plantains, black beans and yellow rice).

Nap time.

Turtle Kraals’ Tower Bar – go upstairs to the Tower Bar for a great view of the marina. Snack on a good bucket of ribs, but drink a few mediocre cocktails.

Schooner Wharf* – an open-air and “shack-y” spot by the water, with live music.

Watched the sunset at Mallory Square – a large crowd gathers to watch the sunset and the variety of street-performers: jugglers, tight-rope walkers, musicians and the like.


Sunset at Mallory Square

Café Sole for dinner- you can escape the crowds in a quieter, more residential section (known as Old Town). Entree was fine, but the strawberries with vanilla ice cream and balsamic reduction was incredible.


Brunch at Blue Heaven* – this is one of my favorite spots. You must We had about a half an hour wait, so we enjoyed bloody marys and mimosas and played outdoor ping pong. Fun and funky eclectic décor of mostly outdoor tables. Try the house specialties: lobster eggs benedict and banana bread. The lobster benedict is pricey, but it is worth it. And the banana bread has to be the best I’ve ever had.

Kayaking at Smathers Beach* – we rented a two person kayak. The water is calm so it is a lot like flat water canoeing.

Walked the AIDS Memorial.

Hogfish Bar & Grill* – this awesome bar and restaurant is actually on Stock Island (next key over). If you have a car, you should absolutely go. Its off-the-beaten-path, pass a few trailer parks, but you end up at the marina. Snack on frozen margaritas and split an order of fish tacos. Great seafood menu and an even better jukebox. A place with Bob Marley, the Big Chill soundtrack, Aretha Franklin, Bob Dylan and David Allen Coe – it is a place after my own heart.

Back to Captain Tony’s for more of the acoustic guitar player. When we walked in he said we must be a glutton for punishment.

Dinner at Hog’s Breath Saloon* – good spot for a quick, cheap (and good) burger and fish sandwich. I think I could eat grilled fish sandwiches every day in Key West.


Last day of vacation is always melancholic, but have a feeling we’ll be back. Drove to Miami, with the top down most of the way.

posted by Ms. S&C

4 responses to “Ms. S&C goes southernmost

  1. Sounds so lovely…

  2. I want your life….for real I do. I easily pictured myself enjoying everything you just wrote. Thanks so much for sharing!!!

  3. Kathy, in response to “I want your life…” — I’m totally flattered, but you know I’m only sharing the good stuff on here, right? Everyday life is pretty good, but it is not a Key West vacay:-)

  4. Ms S&C,

    We also love Key West, and completely agree with your assessment of the dining/drinking establishments. One thing we do on EVERY trip–and there have been several over the years–is go on the sunset cruise. Fury is the best company for this type of excursion and has a great selection of boats and trips to choose from. We liked the glass bottomed boat but LOVE the sunset cruise, and this time enjoyed Commotion on the Ocean. As if the sun, refreshments and fantastic service were not enough, this time we saw tarpon and dolphin. Can’t wait until next year to do it again!

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