If the craziness of Miami has you longing for more laid-back vibes, the Florida Keys are just a short drive away. Key West, the southernmost island, fits the bill nicely with Duval Street bars and gorgeous sunsets in Mallory Square. I highly recommend Key West if you prefer flip-flops over heels, beach coverups to slinky dresses, and dive bars to bottle service. You can easily do this place in a couple of days (perhaps tacked onto a Miami trip) or spend an entire week. Only 90 miles from Cuba (technically closer to Cuba than Miami), this island actually makes you feel like you are in the Caribbean when you're really still in the U.S. No passports needed which makes it a tad easier to access. But there are a couple of items I'd like to address:
- Key West is not known for its beaches. That doesn't mean you won't find any, they are there, they are just not the pristine white-sanded beaches you envision when you think of the Caribbean. And actually, you can find prettier beaches at other Florida destinations.
- Key West airport is very small so don't expect flights to be cheap. This is especially the case over holidays and school vacations, unfortunately.
But don't let the facts deter you. Simply opt for some quality pool lounging and rent a convertible and hit the road (for the most scenic drive in the U.S.) from Miami or Fort Lauderdale where flights are much, much cheaper. Once you've made it over the final bridge in the keys, here's what you should do:
SEE
Duval Street- This mile-long street is Key West's main street that's full of restaurants, bars, cafes and shops. Definitely take a few strolls up and down and bar hop along the way. No need to chug that beer though--with a lax open container policy you can bring it with you to your next watering hole (plastic cups only!).
Mallory Square- The best place to catch one of Key West's beautiful orange sunsets. Live performers, carts selling everything from drinks that light up to Christmas ornaments, and happy people out enjoying life makes this a perfect place to start your night. Be sure to Google the time of sunset and plan to arrive at least 30 minutes before to watch the bright orange circle get sucked into the sea.
Southernmost Point - A life-size buoy marks this spot. Must get a photo with the view in the background. On a clear day you can spot Cuba (just kidding, but you are only 90 miles away).
Ernest Hemingway House - If you don't mind lots of free-roaming cats, and 6-toed ones at that, then visit the famous American writer's home where he lived from 1931 to 1939 and arguably wrote some of his best work. (907 Whitehead St.)
EAT
La Creperie - Both the sweet and savory varieties abound on the menu at this cute little cafe. The owner is from Brittany, France so you can expect these to be as authentic as they get without going to France. (300 Petronia St.)
Margaritaville - I mean, When in Rome! This Jimmy Buffett outpost is the original and in my mind is therefore the best. It offers live music most nights starting at 8p so why not enjoy your Cheeseburger in Paradise and order that Boat Drink? (500 Duval St.)
Ana's Cuban Cafe - A little hole in the wall near the Southernmost point serving up delicious made-to-order sandwiches, Cuban delights and breakfast. (1330 Simonton St.)
Kelly's Caribbean Bar & Grill - For any fellow aviation enthusiasts this is the place to visit because it is the original Pan Am headquarters back when Pan Am was the first American airline to fly an international route - Key West to Havana. The casual restaurant is also the location of the Southernmost Brewery offering beers brewed on the premises. (301 Whitehead St.)
Glazed Donuts - The gourmet donut shop craze made its way to the southernmost point of the continental U.S. to bring you both classic flavors as its name suggests and more adventurous flavors like Key Lime Pie (of course) and candied bacon. Espresso drinks too. Closed Mondays. (420 Eaton St.)
La Te Da - A classic choice if you're looking for a more upscale dinner on a charming, candlelit patio. (1125 Duval St.)
DRINK
Sloppy Joe's Bar - If there's only one place you go to while you're in Key West make it this iconic establishment. Casual bar by day, live music and dancing by night. (201 Duval St.)
Captain Tony's Saloon - Jimmy Buffett fan or not, this dive bar is a must with bras hanging from the ceiling and business cards covering the walls. Sometimes you'll catch a one-man band and his guitar and other times you'll spend way too much time trying to toss a coin over your shoulder and into the mouth of the fish that rests on top of the sign outside. (428 Greene St.)
Hog's Breath Saloon - Another Key West icon with, you guessed it, live music. Belly up to the outdoor bar and feel like you're in a treehouse. Don't be surprised if you get pulled into a conga line; this place can get rowdy but in a good fun kinda way. (400 Front St.)
Louie's Backyard - For a more refined evening, opt for glass of wine with a gorgeous view of the water. Head upstairs for said view and ask for a table on the balcony. You won't regret it. (700 Waddell Ave.)
Sunset Pier - Head to this colorful dockside spot for an ice cold boat drink and sit back and enjoy the sunset. (0 Duval St.)
SLEEP
Casa Marina - Off the quieter end of Duval Street is this grand Waldorf Astoria resort. The pool/waterfront area is one of the prettiest on the island and you can go swimming off the dock into the ocean (a plus when the shore is protected by coral reef). You even get popsicles delivered to your lounge chair. If you're worried about being too far from the action, perhaps a pedicab ride will change your mind. (1500 Reynolds St.)
The Reach - Located next door to the Casa Marina is another lovely Waldorf Astoria resort. Much smaller than the Casa Marina, especially the pool and waterfront, so guests at this hotel are welcome to use the facilities at the Casa Marina if they so wish. (1435 Simonton St.)
The Westin Key West Resort & Marina - Located steps away from Mallory Square, this hotel is a great option if you prefer to be close to all the action. There is no beach here, but the pool is inviting. Guests can choose to have breakfast dockside at the property's restaurant, Latitudes, and watch the ships pull in. (245 Front St.)
Southernmost on the Beach - If the above options are a little too pricey, try for this stylish hotel. From appearances, it looks more like an inn but offers hotel amenities. It is located, as the name suggests, on one of the few beaches on the island just steps from the Southernmost Point. (508 South St.)
Last but not least, if you're lucky enough to be able to visit Key West during the holidays, I highly recommend you do so. Flights and accommodations are pricey but you're guaranteed endless merriment. Palm trees are decked out with Christmas lights, lampposts are decorated to look like candy canes and there are numerous New Year's Eve countdown celebrations to choose from (a pirate sliding down the mast of a schooner....um, yes please). Plus, Duval Street shuts down to traffic to allow for a big party in the street. I promise, this experience will not disappoint.
Whether or not you visit during the holidays, Key West really makes you leave your worries behind and gives you a taste for Jimmy Buffett/Ernest Hemingway-inspired life. It is a crazy but amazing little place that should be on everyone's bucket list. I mean, who can turn down a boat drink while taking in the gorgeous sunset? After all, if we weren't all crazy we would go insane.
Views for days on the drive down to the Keys
The Southernmost Point was getting a fresh paint job unfortunately!
Gorgeous tropical views abound in Key West
Captain Tony's for all you Jimmy Buffett fans out there
The original Pan Am headquarters, wow!
The beautiful Casa Marina Hotel
The grounds and pool area at the Casa Marina
The pool area at the Reach Resort
