Key West, Florida Guide
Key West could best be described as a laid back, island resort town; more importantly though, it's Jimmy Buffett's adopted hometown. Warm weather, tasty restaurants, a carefree culture, and plenty of options for adventure and relaxation await visitors to this island paradise.
When to Visit
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Florida gets hot in the summer, also, water is wet. Summer also marks hurricane season in the Atlantic Ocean, and they've been known to hit the Florida Keys before. My point is, in fall, winter, and spring you'll still find great weather in Key West, without (or at least less of) risk of 130 mph winds and brutal humidity. If visiting in the spring, just keep in mind college break schedules, as the town is a spring breakers destination.
How to Get There
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Key West is located at the very end of the Florida Keys, a string of islands jutting out into the Gulf of Mexico. Key West does have a major airport, but only a handful of big airlines go here, so expect flights to be a little more expensive. Another popular option is to fly into Miami or Fort Lauderdale, Florida, rent a car, and make the 3.5 - 4 hour drive down the coat and along the Keys' famous Highway One. Stopping on and exploring the keys (islands) before you reach the Conch Republic is half the fun.
Things to Do in Key West
Duval Street
Time: N/A.
Distance: N/A.
Is it probably the busiest and most touristy part of Key West? For sure. Is it still worth visiting? Definitely. Stroll Duval Street’s classic and eccentric bars, restaurants, and shops, each more unique than the last. While prices can vary for food and drink, pretty much everywhere runs specials, so a visit here doesn’t necessarily have to be a wallet-breaker. At night, it can become quite busy, so if you’re tired of the crowds, don’t be afraid to explore pretty much any of the side streets off Duval for some hidden Key West gems.
Day or night--there isn't a bad time to explore Duval Street.
Hemingway Home and Museum
Time: 1 - 2 hours.
Distance: N/A.
If you want to see Ernest’s residence closer than the street-view, it’s going to cost you $15.00. This gets you a tour of the home and the gardens, where you’re liable to run into one of the 40 or so polydactyl cats that call this place home. Whether you’re into the famous author, or six-toed felines, the Hemingway House and Museum is another Key West staple. For more information, check out the website here.
Mallory Square Sunset Celebration
Time: 1 hour.
Distance: N/A.
Mallory Square tends to be quiet during the day, but about an hour before sunset, a variety of street performers and musicians fill the area. Enjoy the spectacles as the sun inches closer and closer to the waters of the Gulf, putting on a show of its own. Click here for more information on the sunset celebration.
Performers fill Mallory Square for the Sunset Celebration
The sunsets themselves? They're pretty good too.
About Me
Hi there, I'm Dan: videographer, travel-addict, and beer-lover. I left corporate life behind to start my own video business and travel the world. Want to know more about me and Dan Treks?
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Southernmost Point Buoy
Time: N/A.
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If Duval Street is the most touristy part of Key West, the Southernmost Point Buoy probably takes second place. Located at the corner of Southwest and White Street, expect a line of tourists at the buoy, each waiting to get their picture taken. The hard truth? It’s actually not the southernmost point of the continental United States; but the true point is on Navy land, which doesn’t allow visitors for photo-ops. Missed opportunity, if you ask me.
Honorable mention: Mile Marker 0.
I include this with the buoy since it's the other touristy landmark in Key West, considering it's image is splattered all over memorabilia. Find it at the corner of Fleming and Whitehead Street, or one block behind the original Margaritaville.
Dry Tortugas National Park
Time: 9 - 10 hours (including travel time).
Distance: 70 miles by boat or seaplane from Key West.
One of the most remote national parks in America, it’s only accessible by seaplane or boat. 70 miles off the coast brings you to the Dry Tortugas, a series of small islands featuring coral reefs, shipwrecks, abundant marine life, and a 19th century fort for you to explore. To learn more about the park, check out my travel guide on it here.
70 miles by boat or plane gets you to Dry Tortugas National Park
Bahia Honda State Park
Time: 2 - 3 hours.
Distance: 45 minutes/35 miles from Key West.
While actually about 45 minutes from Key West on Bahia Honda Key, you pass this unique state park on your drive down. You probably noticed another bridge running parallel to the highway, which is the long abandoned Bahia Honda Rail Bridge. Should you feel like exploring it, hitting the beach, hiking or biking some tropical trails, or even doing some Keys camping, Bahia Honda State Park will be right up your alley. It costs $8.00 per car to enter, and you’ll want to arrive early during the busy months, as the parking lot fills fast.
Seven Mile Bridge and the abandoned Bahia Honda Rail Bridge.
Key West Eats & Drinks
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I wish I could eat and booze at all the different places in Key West, I really do. I'd not only be broke if I did though, but I'd be morbidly obese and have stage four liver disease. Instead, here's a small sampling of the places I actually have been to.
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Sloppy Joe's
A Key West staple, you’ll find Sloppy Joes on the corner of Greene and Duval street. If you glance at a coaster (or most other merchandise), you’ll see Ernest Hemingway staring back at you, and that’s because he was a frequent patron of the bar during his time in Key West. It’s probably the most touristy of the Duval Street pubs, but when in Rome, right? Why not pop in for a frozen margarita, or their very own Sloppy Joe’s Island Ale. Like most places on Duval, expect some live music too.
Sloppy Joe's: a Key West icon.
Amigos Tortilla Bar
Home of the square taco! If that’s not enough to sell you, then I don’t know what is. I kid, of course. Amigos' claim to fame is their square tacos though, which apparently hold more and spill less. Once I saw a chorizo option, I knew we had to stop. Sporting classic, Mexican street tacos and large beer offerings, I was in heaven—the chorizo tacos were just as good as I could have hoped, with three on a platter, mixed with fried potatoes and a side of rice and beans. We finished it off with a Key Lime pie sampler, sporting offerings from Kermit's Key Lime Pie and Key West Key Lime Pie Company—you gotta try it at least once while you’re here, right?
The Original Margaritaville
Look, I’m not proud of my love for Jimmy Buffett, and you shouldn’t be either, but the man wrote a song about a cheeseburger, for crying out loud, so really, what’s not to love? Key West boasts the one that started it all: the original Margaritaville. About three blocks down from Sloppy Joe’s... okay look, if you’ve ever stepped foot into the tortured existence of a Margaritaville in any other big city or tourist hot spot, you know what to expect in terms of food, drink, and appearance. This one is actually quite smaller, but still has a stage for live music, and a screen playing music videos--and yep, every third video is a Buffett one, just like every single other Margaritaville.
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Mary Ellen's
I’m not a bad person—that’s how every bad person begins their testimony/child support hearing/7th intervention, right? I’m not a bad person because I love comfort food, and neither are you. Sure, I’ve finished an entire pizza on my own too many times to count, and at Mary Ellen’s, I ordered not one, but two appetizers on top of my meal, simply, because I can. It’s located a block off of Duval Street, and if you’re looking for a slew of local brews on tap, speciality grilled cheese and more, then you have come to the right place. I decided to treat my body right after several days of eating and drinking, by ordering the cheesy garlic bread and cheese-smothered tater tots (you can also add a fried egg and more, if you please) as appetizers, followed by the Guiseppe sandwich, which featured a variety of Italian meats, mozzarella, and marinara on ciabatta bread. I don’t know who Mary Ellen is, but she makes some great food. Stop in for a beer, check out the ceiling covered in Christmas lights, and eat your food there or take it to go—all orders are placed at the take out window, regardless of where you choose to feast.
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Blue Heaven
Honorable mention, because while I didn’t have a full meal here, the internet pointed me in Blue Heaven’s direction for their Key Lime Pie, which was described as some of the most “authentic.” Well what was the other stuff I had then? Either way, it’s nice to get off Duval Street and explore elsewhere. If authenticity is measured by the height of meringue, then Blue Heaven certainly takes the cake (pie?). A quick glance at their menu shows that dinner entrees start at $22.00 and go up from there. It just might be well worth it for the atmosphere though, with a mixture of interior and exterior seating, and the outside’s design akin to being shipwrecked on an island, littered with tiny shacks constructed from wood and tin siding. I know that doesn’t sound particularly appealing, but it actually makes for a very unique setting, especially at night with its mixture of colorful lights illuminating the space. Stop by for a drink at one of the outside bars or a slice of pie, kick back, and enjoy some live music on island time.
They don't mess around with their key lime pie at Blue Heaven
This is just the tip of the iceberg when it comes to good eats in Key West, as there is such a large variety of pubs and places all over old town. My best advice is to explore on your own, and don’t be afraid of the less-traveled places, you just might find your cheeseburger in paradise.
Keep your eyes and ears peeled for Key West's most famous and feral residents.
Where to Stay in Key West
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Hotels and Lodges
Key West isn’t a day trip kind of place, so you’re going to need a place to stay. The island itself isn’t all that big, and can basically be broken down into Old Town and New Town. Old Town is where you’ll probably spend most of your time, where you’ll find Key West features like Duval Street, Mallory Square, the southernmost point buoy, the Hemingway House, and the ferry to Dry Tortugas National Park. It does have a number of hotels and resorts, but since they’re closer to the action, you’re likely going to pay a little more to stay.
New Town on the other hand is more outside of the tourist zone, featuring your usual fast food locales, grocery stores, chain hotels, and a row of newer, more spacious resorts, located pretty close to the island’s entrance. We chose the 24 North Resort, part of what I would call the resort row. We found it on Groupon, for about $110.00 per night, which was the most reasonable rate I could find on the island at the time. It seems like all of the hotels on resort row (24 North, The Gates Hotel, the Hilton Garden Inn, and a few others) are usually within $10.00 - $15.00 per night of each other, and many actually share some facilities: the Gates Hotel and 24 North share an outdoor bar and restaurant, as well as a free, daily shuttle service to Mallory Square.
The 24 North Hotel is fairly new, and still has that new feel and look to it. A large pool area in the back, the aforementioned bar/restaurant combo next door, a Starbucks, and a permanently stationed food truck called the Blind Pig means you’ll have no trouble getting your snack, booze, or caffeine fix. Our king-bed room was on the fourth floor, and had all the amenities you’d expect from a hotel room: Keurig coffee maker, clean sheets and linens, full size shower, no rotting corpses stuffed under the bed—it was fine. If you’re looking for a little more flair, maybe consider one of the larger (and more expensive) resorts near Old Town.
What would Jimmy Buffett do? He'd visit Key West.