In a three and a half hours car ride you can find yourself in Orlando’s Margaritaville or in the real life Margaritaville of Key West. While a weekend with the Mouse is always a good time, a weekend walking around, drinking all day and hanging with the cocks that roam wild in Key West is a reason to head south.

Buy yourself a towel with the Key West motto, “the lower the latitude the better the attitude” and get into the Conch Repulic spirit. That means parrot heads, fried fish sandwiches, conch fritters upon conch fritters and craft beers – yes, craft beers. A town that was once known, and really still is, for strippers, biker, gay biker strippers still has all the kitsch that’s made it a popular cruise destination, but there’s another way to see Cayo Hueso. This tiny island is brimming with the weird, the local and the hidden, treasures including a very decent culinary scene.

Sure there’s the drunk pirate thing, but there’s also a living spirit of quaint charm. The homes are lovely, the people are lovely and event the automobiles are lovely. Look for touches of bohemian luxury amist the sea of Thing 1 and Thing 2 tshirts.

Here are a couple places to hit on a weekend trip to Key West:

Where To Stay: Frances Street Bottle Inn Bed & Breakfast

This historic bed & breakfast hotel has exactly what you want from an accommodation in Key West, a wrap around porch, a kind and chatty owner who doesn’t give all up in your space but makes for nice conversation, breakfast waiting for you in a dining room and a clean room with a blend of Caribbean and European simple and homey décor.

A short walk or bike ride away from the main strip in Key West, it’s nice to be a bit away from the drag of oversized neon cups and too loud celebrations when you’re finally ready to get some shut-eye.

The Bottle Inn was once a corner grocery, a boarding house and now a remodeled inn that looks like the exact home you’d want if you moved to Key West. And trust me, while you’re in Key West, you’ll find yourself thinking of moving there, of chasing the dream like so many before you, of tending bar or learnining to cook French food or taking up ceramics or giving ghost tours and just kickin’ back Conch Republic style.

535 frances street

Besame Mucho

Just next door to Blue Heaven is a shopping experience that feels part Parisienne apothecary, part cathedral gift shop in South America and part Key West at Besame Mucho. Well known as the best boutique in Key West, this store in a converted traditional Key West style home (like most of this a must stop for enthusiasts of window-shopping and gatherers-of-all-things-unnecessary (but so pretty!).

Soy basil mint and coriander candle in a glass votive? It can be yours for ten dollars! Porcelain naked blushing human dolls – there must be an explanation – it would look so good on a… dresser? Natural sea sponges for $22. How have you lived without them?

Jokes aside, this is a meticulously curated store with a story behind everything. Ask the friendly, and stylish, staff what the metal trinkets in the shape of body parts are and they’ll tell you all about the Mexican miracle charms. Whether you have a dorm room to decorate, a gift to take home or a whole house to fill with these treasures – stop by Besame Mucho and find something you didn’t even know you were looking for.

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315 petronia street

Blue Heaven

Everyone will tell you to go to Blue Heaven for brunch in Key West. Take their advice. When you get there, there will be a wait. Wait. This place is the Key West truth. While you're waiting you can go to Besame Mucho, conveniently located right next door.

Roaming cats and cocks. Strong Bloody Marys. Live music best listened to from snapped plastic patio chairs. And the pleasant, ever pleasant blend of sweaty mid-westerners, college-spring-breakers who’ve decided to keep drinking to ward of their hangovers and 50 – 60 something’s who have perpetual hangovers.

729 thomas street

Dog Friendly

Key West is the most dog-friendly place I’ve ever been. I’m not in the habit of traveling with my dog, but a short car ride, a pet-friendly b&B and a slew of dog friendly outdoor bars was too tempting a vacay to pass up for my pal Roo.

Go ahead, take your dog with you and don’t feel weird about it. My pup was the happiest he’s ever been and the most tired he’s ever been. Every place in this list is dog-friendly and were more than happy to seat us with our little pup.

B.O.’s Fish Wagon

This wooden wagon serves a menu split by “Landwiches” and “Seawiches.” Stick to the sea options and (fried grouper sandwich, fish of the day sandwich, soft-shell crab, cracked conch) order a side of fries or beans and rice. This tight menu goes down well with a cold one, like everything else in Key West, and won’t disappoint.

Don’t be weary of waiting in line. It moves fast, the kitchen runs like a well oiled machine. Make friends with the frat guys sitting next to you or share a communal picnic table with a bachelorette party.

801 caroline street

The Kitsch

A bar filled with bras and panties. A painted postcard coconut souvenir. Hot sauce. Key West is the capital of kitch, just soak it up.

The Porch

Right on Carolina Street, just off off Duval’s stretch of shots, shots, shots, shots, shots, is one of my favorite bars in the world. The Porch is a craft beer bar in an old home with some of the nation’s best craft beers on tap. It’s not that the selection of beers here is the best ever, although, it’s very comprehensive and the wait staff has a very solid knowledge, it’s the kind of low-brow meets high-brow, locals and curious tourists that makes this place special.

The typical Key West characters line in the inside bar and strike up conversation with anyone who gives ‘em a sideways smile. It’s a place that feels new and yet, not pretentious, where we went and sat on the porch with our dog two days in a row and has a waitress that recognized us.

The space is a mishmash of light-filled mansion and heavily draped saloon. The Porch is perfect place to start your Ghost Tour.

429 caroline street

Ghost Tour

This guy roped us into a ghost tour. He didn’t really have much roping to do. He was missing teeth, the tour started at The Porch, our new favorite spot and the guide was names Southernmost Ted. If you need a paranormal pick me up on your Facebook once in a while, follow Southernmost Ted. If you want someone who is so fully and totally devoted to the spooky and strange to convince you Key West is among the most haunted places in America and full of orbs – take Ted’s tour.

Start your walking tour with a beer – seriously, we told you their into their ice colds in Key West, and get ready for a bunch of bonding with strangers who are also there to hear stories of brides keeping their dead husbands in their homes, murders and children haunting for centuries. Start skeptical, end skeptical, start a believer and leave confirmed and go along for the ride.

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429 caroline street

JANGEORGe Interior Design

The general design style of Key West is kind of like a squinting drunk pirate who likes the colors of the Crayola classic box and thinks neon beer signs belong in the living room. At JANGEORGe, you’ll find what’s pretty much the opposite. Simple, stark minimalism with eco accents and natural fibers naturally paired with white mid-century modernism.

Pepe’s Café

Pepe’s is the oldest eating house in the Florida Keys, they call themselves “a fairly good place, for quite a long time.” Boy, do I love some good modesty. 100 years old in 2009, Pepe’s feels a little bit Frank-Sinatra-does-Key-West. Eat there for breakfast, lunch, dinner or a mid-day drink and oyster snack. The menu is filled with old-timey classics like Chopped Beef Dinner, Oysters Florentine or Gulf Oysters eaten raw, New York Strip and Pepe’s Steak Smothered in Pork Chops –not sure what that last one means, but I can vouch for a very decent plate of oysters and a sweet and dessert-like spiked coffee drink.

806 caroline street

travel guide: key west