Key West is the last in a chain of islands off the southern tip of Florida. Made famous by Ernest Hemmingway, Jimmy Buffett, Harry Truman, and others, Key West has more than its share of folklore. Once here, you can see why. It is a funky paradise, the stuff dreams consist of: Blue water, palm trees, good atmosphere, and bad behavior. Something happens at the end of the line — it’s a little bit magic, a little bit tragic, and a good time all the way.
We love Key West and cannot wait to return (without the kids). Below are the best ten things we did, as well as some things we look forward to doing next time.
At sunset, it feels as if the entire island gathers in Mallory Square to watch the celestial show. Grab a seat on the outer wall facing Sunset Key and dangle your feet over the edge. You will have to get there early, before the crowd files in. Most folks will watch the sunset over the heads of the people in front of them, which to us is a lesser experience.
Mallory Square is also a place where street performers engage circles of tourists. The Key West Aquarium is nearby, as is the Playhouse, the Memorial Sculpture Garden, Trolly Tours, and some large gift shops.
Be sure to catch a world-famous sunset here – it’s a must.
Beginning in Key Largo and running 100 miles till it’s out of road, the Oversees Highway might be the single coolest thing you’ll see on your Key West vacation. The highway alternates from land to sea, a pleasing rotation of tropical isles and elevated bridges over blue and green water.
The pilgrimage to Key West from mainland Florida will build excitement as you wind your way into the keys. If you fly directly into Key West, consider renting a car and taking a half-day drive up the chain and back. The highlights of the ramble are when the bridges span the larger channels, the longest of which, Seven Mile Bridge, is the quintessential stretch.
I’m a huge Hemmingway fan – The Sun Also Rises is one of my favorites — so the tour of his Key West home was special. A true American icon, Hemmingway lived a colossal life. He signed on to the Red Cross during WWI at age 18, where he survived mortar fire. He also survived a car crash, a brushfire, and two plane crashes in his lifetime. For years he dazzled Hollywood and won a Pulitzer prize. In his free time he hunted lions and other beasts. For the heck of it he hosted boxing matches at the piers of Key West and faced all comers. What literary master does these things?
The house is a joy to explore. Some of the things you’ll see: his writing den, his remarkable pool and “his last penny”, and the famous six-toed cats. During the tour you’ll learn about his mental illness, his many wives (terrific folklore), how he came to Key West, and the origins of his incredible novels.
About 75 miles north of Key West is Robbie’s of Islamorada. Equal parts beach bar, restaurant, gift shop, and excursion hub, it would be hard to overstate how much there is going on here. We cannot imagine why anyone would drive past Robbie’s and not check it out.
Lurking near the docks out back is a school of tarpon. A tarpon is a large, green, tropical fish with a hurking mouth. A big one can reach 8’ in length and weight over 200 lbs. Frightening as it may be, you can purchase a bucket of frozen fish and feed them to the dinosaurs. Just dangle the little bugger off the side of the dock and try not to wet yourself. Its pure terror mixed with fun and sure to make PTSD memories for the kids.
If you come to Key West, you’ll end up here. The bars, the music, the food, all the lyrical Buffet references, the alluring magic of Key West lore is summarized on this iconic street.
You want killer live music at night? Get it here. Looking for creative bars and restaurants? This is the place. Drunken idiots on mopeds, yup! Lots of them right here. Are you dying to see sloshed middle-aged women in ridiculous t-shirts on six-seater bicycles? Of course, you are. We all are. Get it here. See you next week.
There are only four “__most points in the continental USA”. One is in Angle Inlet, Minnesota, so this is one of the three you might actually want to visit (Lubec, Maine and Cape Flattery, Washington are the others).
It makes a fine photograph everyone should collect. Chances are you’ll have to wait in line. Click here for map.
When you picture that lazy, Sunday morning breakfast with the palm trees and acoustic guitar, you are picturing Blue Heaven. The staff is friendly and the food is tremendous. The vibe is pure Key West, with all its multi-colored, ramshackle charm.
Monica ordered the fruit plate with the banana bread and the Lobster “BLT” Benny (eggs benedict). I doubt we’ve ever had better (of any of it). Ryan ordered the omelet and it was very good, and the kids were happy with their pancakes. We wouldn’t dare return to the keys and not stop here.
Probably the two most famous bars in town. Sloppy Joes sits at the intersection of Greene and Duvall and you cannot miss it. Captain Tony’s is located a couple hundred feet away on Greene, in the location of the original Sloppy Joes.
Joe Russell opened Sloppy Joes on December 5th, 1933, the day prohibition was repealed. 3.5 years later he moved his bar to its current location on Duvall Street over a $1 rent raise. Sloppy Joes was the haunt for Hemmingway and the mob of infamous conches that kicked around at the time. Joe and Hemmingway were fishing buddies and share a long, storied history. Today, Sloppy Joes remains very much the same as it once was, serving liquor, and food, and noise.
Captain Tony bought the old Sloppy Joes in 1958, after arriving ten years earlier with $18 in his pocket. Originally a morgue, it is now a classic dive bar with a tree growing in the middle of it – upon which 75 people were hanged (because it was next door to the morgue). It’s considered haunted, but that doesn’t stop the place from packing with partiers on a nightly basis. The walls are covered with ID’s, dollar bills, license plates and bras, and if you go to the men’s room, you’ll see the framed lyrics of Jimmy Buffet’s classic song, Last Mango in Paris, supposed written by Tony himself.
This Korean taco truck serves maybe the best tacos we’ve ever had. The flavor of their Korean BBQ Taco is insane, just listen to these ingredients: Marinated beef short rib, napa cabbage, scallions, carrots, daikon, cilantro, citrus soy dressing, and sriracha. Skip this place and it’s your loss. 409 Caroline St.
Key West is home — probably — to Florida’s most famous treat, and the greatest of all regional American deserts, key lime pie. They aren’t really sure who invented it, but they have some ideas.
You’ll have no shortage of places to order the delicious desert pie. We recommend Kermit’s Key West Key Lime Shoppe. They sell all things key lime, from candy and soda to spice rubs and dog treats. Most of all, they serve the best key lime pie we’ve ever tasted. Blue Heaven also has incredible pies.
Best with children: Robbies, Duvall Street, Mallory Square
Best time to visit: Spring/Fall
RV Camping: Blue Water Key RV Resort; $112-237
Map of Key West: Click Here
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