The colorful road to Key West is paved with happiness. Driving on Overseas Highway is anything but dull. You will be tempted to make endless pit stops on your way down. Given the drive from Miami will take almost four hours non-stop, stopping too often will significantly delay your arrival. I can’t blame you, though. Each section of the drive offers beautiful and interesting features unique to the Florida Keys: endless mom and pop shops, crystal turquoise waters on either side of the road, mangroves, key deer crossings, and fresh seafood everywhere you look. If you start your drive in the late afternoon, you might even catch a glimpse of that Key West sunset right as you arrive. I suggest doing stops on the way back. Trust me when I say, you won’t want to leave. Delaying your departure by exploring the rest of the keys will help you reminisce about your trip: even it that means finding yourself with a giant lawn flamingo you just had to purchase “when you were in Key West,” a month later.
Even though island time and a laid-back attitude are synonymous with Key West, realistically speaking, you will probably use your room just to sleep (and only because our bodies require doing so). There is so much to see and do. Who has time to stay indoors? For luxurious digs, reserve at the Sunset Key Cottages. Seven minutes by launch off the key, the island is surrounded by water and perfect if you need the utmost privacy. If you prefer to stay on a more historic site, head to the Southernmost House. Built in the late 1800s and located on the quieter southern end, this Queen Anne Victorian beauty has been exquisitely restored. Just a single block from Duval Street, charming Simonton Court offers it all: location, privacy, and history. This former cigar factory now houses cottages of all sizes nestled among lush gardens. Right on Duval Street, you can walk just about everywhere from La Concha Hotel. If you want to be where the action is, look no further.
Sure, you can find a Starbucks or two while there, but don’t. Visit Cuban Coffee Queen. The tiny waterfront shack serves up espresso to-go all day long. Order a Cafe con Leche to get started with a punch or perhaps a Hang-Over Helper after your very first indulgent Key West night. Accompany it all with a generously buttered Cuban Tostada. For an authentic Keys leisurely breakfast, choose Banana Cafe. Offering French-Caribbean options, their crepes are standouts. If late-night breakfast is more your thing, keep Sandy’s Cafe in mind. Attached to a laundromat, (yes, you read right) not only can you get your cafecito fix here late into the night/early morning, but you can score some serious Cuban sandwiches too! On your last day as you leave Key West behind, drive north and treat yourself to brunch at The Dining Room on Little Palm Island. Make sure you have reservations. Set off Mile Marker 29, their ferry takes you to Little Torch Key where the resort is located. Luckily, off-island guests are allowed on the premises on Sundays.
It should not come as a surprise to find out that Key West is heavily influenced by the flavor-of-the-moment island of Cuba, just 90 short miles away. Naturally, there is no shortage of seafood and authentic Cuban chow. El Siboney on Catherine Street is the real deal. Buenísimo! There might be a wait; the secret’s out and the lines can get pretty long. But no te preocupes, with their usual quick turnaround your hangry attitude will be short-lived. There’s nothing a good picadillo, puerco asado, or some sweet plantains can’t fix. This next heavy-hitter lunch spot might escape most typical tourists. Set inside a beat up, open-air shack, B.O.’s Fish Wagon delivers big. No shoes? No problem. The fried grouper sandwich served with Cuban bread and slathered with mayo is la-te-darn good. The must-order dish? Conch fritters (order extra sauce). One bite of these hot babies and you too will be hooked forever. Who cares if you are sitting on lopsided picnic tables with roosters and cats crossing right by your feet? Wait. What? #truestory
Dinner and Sex
If you weren’t able to stay on Sunset Key, this is your chance to visit the resort. Latitudes is one Key West’s prime spots to catch the famous sunset. It also happens to be the key’s top casual fine-dining restaurant. On the complete opposite end of the dining spectrum is Angelina’s Pizzeria. Tiny, divey, crowded (and even service with a scowl), yet everything you want at 2am. Just to be clear, it’s not an award-winning recipe, but every slice is tossed and baked to order, served piping hot, and pure late-night heaven. There’s a reason it’s been there for at least two decades. Hidden off the beaten path is Santiago’s Bodega. Delightful tapas, paired with the rustic and quaint chic interiors, continue to be their recipe for success. Original to the area, Better Than Sex serves up cheekily named desserts and a sexy attitude. Fancy a Dark Chocolate Rim Job or a Cookie Nookie Pie? They’ve got ‘em…and more. Deep reds and dimmed lighting await at this sinfully decadent locale.
Drink and Dance
Fun in Key West can take just about any direction you want. What happens in Key West, stays in Key West (unless one of the many live cams caught it. Oops! You have been warned). During the day, splashing in Dante’s Pool Bar can be fun. The self-proclaimed “aquaholics paradise” is a public pool. Add a DJ, alcohol, and an ongoing stream of partiers and well, it’s quite the hopping people-watching place to be. If that’s not your scene and you prefer a more relaxing environment, then stroll on Duval right up to The Porch. This mostly locals’ craft beer bar doubles as a hideaway from the rowdiness that can sometimes overtake Key West. Just another short walk away, Irish Kevin‘s is a lively choice to kick off your night. Live entertainers play some of your favorite songs and hilariously interact with the crowd. Across the street, the Rick’s Bar entertainment complex houses eight different bars. Want some live rock? Durty Harry‘s is your spot. Fancy some Pitbull or some salsa? Head on over to Rick’s. Esta fiesta no termina!
Last tip: beware of rooster crossings. It’s a Key West thing. These unexpected island residents are actually of Cuban descent (bred initially for cockfights centuries ago). Thankfully, that’s no longer legal, but the roosters remain. Cock-a-doodle-do, my friends. Get thee to MM zero, Margaritaville awaits.