Key West Beach 3-23-2011

Give me the Keys.

The weekend getaway is easier than you think. And it’s just what you need.

Right about now, you’re remembering that there actually is a time of year when your go-to-hell pants are not only fun and slightly irreverent, but practical. And we’re not referring to that wool pair you picked up for the holiday party embroidered with candy canes. No, we’re referring to that perfectly-beaten-in, washed-in-saltwater, pair of Nantucket reds currently sitting in the back of your closet.

But, even if winter is technically over, it’s still cold outside. Really cold. You need an escape. After all, there’s only so much Paul Theroux or Ernest Hemingway a man can read.

Our advice? Don’t think too hard: find someplace warm and go there. Get back to the basics: eating, drinking, and being merry. Here are a few tips on how to do it right.


The plan.


Hemingway had a few good habits worth picking up. One in particular was his appreciation of Key West—the perfect setting for us to illustrate the art of getting away.


Why Key West?


Well, it’s easy to get to. And it’s as close as you can get to going “Caribbean” without having to travel to another country. Which is perfect when you’ve got a long weekend and can’t afford to lose one minute clearing customs or waiting in line at immigration. With Key West, you don’t need a passport. And you shouldn’t need to check any bags. Just book your ticket and go. And we mean now. You’ll thank us later.


The traditional watering hole.


Once you’re there, a proper cocktail is not what you need. You’re looking for tradition, sincerity, and a drink. In Key West, you’ll find it at Captain Tony’s Saloon. In the 1930s—when it was still called Sloppy Joe’s Bar—Ernest Hemingway spent many a night here. It’s considered to be the oldest bar in Key West, so it’s fair to say it’s been vetted. Jimmy Buffet played there when he was first starting out. It’s that kind of place.

Captain Tony himself (definitely click on that link) was actually elected mayor of Key West at one time. It’s that kind of town.

Whether you’re in Key West or not, you need to find—and frequent—this kind of place. It’ll put you at ease, soothe your winter wounds, and you won’t feel like you’re stuck in Times Square.



Stay local.


Where you choose to stay could make or break your entire trip. You want to be right in the thick of things, but you also don’t want to feel like you can’t get some peace and quiet. It is a vacation, after all. So, split the difference. Find a place close to the activity, but not truly isolated. In Key West, focus on the western part of the island and find a place where you can easily walk to Duval Street.

Make sure to find a locally owned and operated hotel or bed and breakfast. You won’t regret the personal touches and the invaluable local insight. Besides, you get enough of the chain hotels on business trips.




Eat local.


The fact is, if the city you’re heading to has a restaurant app and you rely on it, you’ll probably end up in the wrong spot.

Same rule applies to Key West: eat what the locals eat. Consult your bartenders and cab drivers. The guys singing at Captain Tony’s? They live in Key West. You may have to work through a few, but eventually you’ll find a resource you can trust.

Take BO’s Fish Wagon for example, home of the (often debated, but we’ll take a stand here) best conch fritters in the Keys. It started as a street vendor in the corner of the parking lot across from Pepe’s Cafe (another Key West must for superb fish and a great local scene). BO’s Fish Wagon still occupies the corner of that same parking lot, and after a long day of sun, food, and drink, it’s just what you need to finish the night. But, unless you ask a local, you’ll probably miss it.


The tourist thing.


Every town has its own real characters and stories, and Key West is known for a few. Arguably one of the more famous was Hemingway. That said, why not visit his polydactyly cats? (Many of the cats in residence have an extra toe or two.) In Key West, you can actually visit and tour Papa’s house, complete with the 60 or so cats that live there. Is it a bit touristy? Absolutely. Do you have to buy the key chain? Maybe. Will you regret not visiting? Of course, you will. You’ll want to be able to regale your friends about how you visited Hemingway’s house, then went to the beach and looked towards Cuba as the sun set. Sounds nice, right? So, give in and go.

Never be afraid to find that one thing—touristy or not—to do in your city of escape. Remember, the place became famous for a reason; you don’t want to miss it.

Just don’t forget the go-to-hell pants. And you can still bring The Old Man and the Sea. A man’s got to read.

So, where will be you be heading for your getaway?

TAGS: Duval Street | Go-to-hell pants | Hemingway | Jimmy Buffet | Key West | Paul Theroux | Travel | Vacation

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  • avatar
    The creperie on Petronia is very good. Too crowded for breakfast, aim from brunch. The Sunset Deck at the Westin on Mallory Square is a great spot for a drink. You can see the craziness of Mallory Square but still have great cocktails
    43 months ago | Report abuse |
  • avatar
    Very excited for this summer - just finishing up plans for a trip to Italy! Thanks for all the tips, I definitely will use them.
    43 months ago | Report abuse |
  • avatar
    I just got back from Key West on Sunday. I took some of the advise from this post when planning my trip. It was great.
    41 months ago | Report abuse |