DO - Take a few extra sick days. One isn’t going to cut it
DO - By boat, kayak, or paddle board…get out on the water
DON’T - Do it without a guide
DO - Wait for a table at Blue Heaven
DON’T - worry about the wait, they have ping pong
DON’T - Go on the party boats
DO - Buy sunscreen
DON’T - get stuck on Duvall street
DO - Beat those late-night cravings with Dion’s fried chicken
DO - Get off the main roads to discover the island’s true personality

For everything else, we’ve highlighted our picks on where to play, eat, drink and stay. Onward.

Getting to Key West isn’t easy, but we promise it’s worth the four hour drive from Miami. Give yourself a full day to get there, and you’ll enjoy the destination that much more – especially if you stop to feed the giant tarpon at Robby’s, or at the Rain Barrel for kitsch and a conch shell.

On Labor Day in 1935, the Florida Keys were devastated by the most powerful storm to ever make landfall on the United States in recorded history. The railway neighboring the Overseas Highway was never rebuilt, and its rusted skeleton accompanies most of your drive down.

If lobster is on the menu, cook’ed super-slow and with lots of butter. The locals’ tip is to get garlic bread at the dollar store, scrape of the butter, and use it as your dipping sauce for the lobster once fully cooked.

CUBAN COFFEE QUEEN, 284 Margaret Street
Good morning, go here, you're welcome.

SANDY’S CAFE, 1026 White Street
After spending a day snorkeling or fishing, there are few things that taste better than a perfectly grilled sandwich, shoestring potato fries, and a fresh slice of Key Lime Pie.

Speaking of Key Lime Pie, it’s everywhere, but you’ll want to be selective. The true Key Westers know that the best meringue on the island can’t be found anywhere but their own kitchen…but you’ll wanna get a slice at Blue Heaven anyway.

HOGFISH BAR & GRILLE, Stock Island
On your way down or on your way home....Insulated from the hype and commotion of the tourist spots, the Hogfish feels like a true locals’ haunt with food that sticks to your ribs and beer that’s always free – tomorrow.

‘Round these parts, your choices are generally: “raw or barbequed,” “ grilled or fried,” and “blended or on the rocks.” If there are more, you might not be far enough from the mainland.

Be sure to order like a local, and always start with conch fritters. These fried nuggets of onion, garlic and snail meat are delicious – thankfully they can be found just about anywhere. Our favorites are at a colorful dive just as you enter the keys, Alabama Jacks on Card Sound Road. Oh, and it’s pronounced “conk” (unless of course you just watched Lord of the Flies)

Eating on the island has many sides – from back-alley sandwich huts, to tourist hotspots where the day’s cruises unload directly to the margarita bar. Most spots will happily cook whatever you pull out of the ocean.

PEPE’S CAFE, 805 Caroline Street
There is no shortage of proper watering holes in Key West, but Pepe’s is a favorite. Founded in 1909, this cafe lays claim to being “the oldest joint” on the island – and with an easy going menu of fresh comfort food and cheap cocktails, we sure it’ll be around for another 100 years.

Breakfast as Pepe's once cost 75 cents.

This place isn't over the top and that's what's perfect about it. Old Florida feel, taco truck out back, it's perfect for fresh off the water, kickin' back with a beer and hanging out with friends and family.

AFTER HOURS, Green Parrot
Nicknamed “a sunny place for shady people,” the venerable Green Parrot Bar feels like a local dive, but is routinely counted amongst mentions of the best bars in America. Check the live music calendar before you go.

The Green Parrot is more than a bar; it is a Key West icon.

It's a lot of stairs but you'll never forget the view at The Garden of Eden. A roof top bar above the the Whistle Bar...midnight is a great time to go.

DION'S QUICK MART, Hwy 1 & White
Best place for the post-bar-crawl crash at 2am? Dion’s Quik Mart. Trust us on this – the spot doesn’t look like much (it’s a gas station, after all), but the fried chicken is good enough that we couldn’t wait until the middle of the night to try it.

BLUE HEAVEN, 729 Thomas Street
If you’ve got a hearty appetite and a hangover to beat, we recommend doing so  1) with a mimosa in hand, and  2) at Blue Heaven, where ping pong and live music make the usually long wait times fly by. We'll see you here the day after the wedding.

EDEN HOUSE, 1015 Fleming Street
It's quiet, the pool and surrounding gardens are beautiful, and they have a complimentary happy hour, every afternoon on the dot.

Key West is a place that embraces its own with charm and eccentricity, and with a cocktail that’s equal parts raunchy and elegant. It’s also a place whose rowdy nightlife and legendary bar crawl sharply contrast the sleepy clapboard houses, lush gardens and the unending vastness of the ocean on three sides – altogether perfect places to feel small, but for completely different reasons.

Every day carry essentials (EDC) around these parts is pretty straightforward: camera, sunglasses, and bottle opener. The importance of the latter cannot be overstated.

HEMINGWAY HOUSE, 907 Whitehead Street
Though this two-story Spanish colonial estate was Hemingway’s home between 1931 and 1939, you could say he really lived at local watering holes like Captain Tony’s. Legend has it, he’d belly up to the bar where he’d be presented with his drink and typewriter already set with the manuscript – just as the thirsty author had left it the night before last call.

As the story goes, Hemingway was given a white, six-toed cat by a ship's captain (making him a #catdad since long before it was a thing). Many of the cats on the house's grounds – and to an extent, some on the island – are descendants of that original cat, named Snow White.

In Key West, you’re an awfully long way from damn near anywhere. For most destinations, the distance is unapologetic, which is why many people have come here looking to get a little lost and happily end up staying that way.

KEY WEST
“…offers a glimpse of the under glimmer…an experience of the deeply real that lurks everywhere beneath centuries of stereotypes and false images that prevent us from truly seeing other people, other places, other times.”

Author Phil Cousineau