ome people might wonder: Why would a person go all the way to the southernmost point in the continental United States for a fish sandwich? Well, the short answer is that we didn’t go to Key West just for a fish sandwich — we scoped out a hotel, went fishing, drove scooters and jet skis, and drank beer. The long answer is that the hogfish isn’t any old sea critter you can pick up at Whole Foods, and the place that serves it ranks very high on the list of best waterfront bars in America (just behind the Beachcomber in Wellfleet, MA, in this author’s black book). We were principally after a filet of fish. Besides, if you get just one good memory in 72 hours, that’s a pretty good one, for a long weekend.

MORE TRAVEL: Exploring Actun Tunichil Muknal Cave | Harvesting Champagne | 72 Hours in Edinburgh

Key West History, Abridged

When visitors touch down at Key West International they’re greeted by a sign: Welcome to the Conch Republic. On its face this slogan is just like any other expression of hospitality — Welcome to Maine, The Way Life Should Be; Tennessee, the Volunteer State, Welcomes You; Ohio Welcomes You, The Heart of It All! — but for the fact that Key West is not its own state, least of all its own republic. In this seemingly benign greeting lies a bit of mischief: For a brief moment in the ’80s, Key West seceded from the U.S.A, symbolically anyway.

In 1982 the U.S. Border Patrol set up a blockade in Florida City, just north of the Keys. The purpose of the blockade was ostensibly to stop illegal immigrants from coming up to the mainland, but residents of the Keys perceived this as an act of tyranny. Key West Mayor Dennis Wardlow convened with other community leaders and announced secession, adopting the Conch Republic as the new name of the territory (“conch” describes the Bahamian settlers of European heritage who moved to the Keys in the late 1800s).

He then struck a man in a naval uniform over the head with a piece of stale Cuban bread, symbolizing war, surrendered to the same man, and declared the rebellion over. Some locals like to joke that they’re still waiting on reparations from the U.S. government.

Hemingway, Fishing and Beer



It’s nice to have fun pictures of ourselves. Most of the time we can get these from friends, family, wedding photographers. But sometimes nobody else is around and we’ve got to record the mischief ourselves — like this scooter bound mayhem, which provided the final testing ground for our capstone thesis. Here’s how to do it. – JB

1. Rule #1: Be somewhere interesting or otherwise desirable, e.g., a beach town, space, or drumming on the Tsar bell at the Kremlin.
2. Think about why you’re taking a self portrait. If it’s for a dating site or sexting conversation, stop and reconsider. Proceed with caution.
3. Put your shirt back on, unless this is an underwater shot or you’re drumming on the Tsar bell at the Kremlin — in which case, good on you.
5. Position yourself to get the maximal sense of place in the background and at least half your face.
6. Make a ridiculous face.
7. Snap photo.
8. Thank the Powers That Be you didn’t crash. Send photo to your best buddy and start planning your next adventure.

If we have any criticism of Key West, it’s that the island seems to ride its history pretty hard, from the secession anecdote to Hemingway’s tenure on Whitehead Street from 1931 to 1939. This may be mostly for the benefit of the 800,000+ tourists who dock briefly in Key West aboard cruise ships every year, but it can be a little grating for somebody who wants a slightly spontaneous experience. The Hemingway House is worth a visit to pay your respects and walk the same grounds as a fine writer, but know that the relationship of the items to the man — including the 60 or so polydactyl cats — is apparently questionable.

Hemingway nevertheless is an important figure in Key West history, and his time here serves as a valuable guide for what to do over a long weekend, namely, fishing and drinking beers. There’s excellent fishing to be done in and around Key West: flats fishing for tarpon and bonefish; deep sea fishing for marlin, sailfish and tuna; or just getting out on a charter for a few hours to snag a grouper for dinner. (We reeled in a beautiful blackfin tuna, but forgot the camera that morning… you’ll just have take our word for it. It was a good fight with a strong and noble fish.)

Back on land, Hem and writer pal John Dos Passos were known to hang out at Sloppy Joe’s, an institution for boozing since just after Prohibition, owned by a former speakeasy proprietor name Joe Russell. This place is right at the heart of Duval Street, the main tourist drag, and its good for a beer or two before it things start to get messy as the crowds converge after dinner. Our preference is for Turtle Kraals and Schooner’s over on the marina, both conveniently located next to B.O.’s Fish Wagon, a hovel of a joint that serves conch fritters and a fried grouper sandwich well worth the couple of dollars it’ll cost you.

Hogfish, Scooters and Beer

We reserved the last day of our trip to buzz around the Key West on a scooter — the best way to get around a place that’s only 7.4 square miles and has lots of nooks and crannies to explore on foot. One of those is Fort Zachary Taylor Park, or Fort Zach, a Civil War-era fort that’s also the best local beach for a morning swim.

Ultimately, though, we were just filling time before a leisurely afternoon-turned-evening at the Hogfish Bar & Grill. The bar’s namesake, a member of the wrasse family, is a large, colorful fish with a laterally compressed body and a pig-like snout it uses to root out crustaceans for food (hence the name); it’s native to the Keys; it is fished exclusively by men and women with spears; and it is a sequential hermaphrodite, which means that is starts life as a female and then becomes male.

The bar is likewise unique, tucked away on Stock Island, a 20-minute drive east across the Overseas Highway from the central arteries of Key West activity. It sits directly on Safe Harbor, next door to what the owners claim was HQ for the Bay of Pigs Operation. Whether this is true or a friendly exaggeration is really irrelevant: there’s a pool table, a jukebox, lots of beers on tap, and a placid marina with fishing boats and yachts trolling in and out. It’s an idyllic setting to eat the house special, a fried hogfish sandwich covered in swiss, onions, mushrooms and tartar sauce.

As the sun went down we settled up and revved the scooter’s lawnmower engine just as loud as possible, and, sated like a hogfish with a belly full of crustaceans, made for the airport feeling pretty glad The Conch Republic never officially cut ties with the U.S.A.

MORE SWEET TRAVEL: Exploring Actun Tunichil Muknal Cave | Harvesting Champagne | 72 Hours in Edinburgh