My Favorite Key West Secret

It’s a rainy, wet, dreary day today, the perfect kind of morning to curl up on the couch with some Earl Grey and Jane Austin or “Seven Years in Tibet“. Or, alternatively, we can cast our minds to beautiful places far away, whether to daydream, plan, or remember. We can visit tropical wonderlands like Key West.

Today I’m going to tell you a secret, a traveler’s secret. You know my favorite kind of secret? When you go somewhere you’ve never been in your whole life and you can still show someone something amazing your first time there, something totally unexpected and marvelous?

This was a something passed on to me and now I can share it with you. But let’s keep it special, shall we?

The island of Key West is at the end of one of the most gorgeous road trips in the whole world. If you’ve never been to a tropical paradise, you may be unprepared for the turquoise blue of the water or the impeccable visibility, falsely attributing it to some kind of Instagram filter. You may be surprised by the colorful birds and fish, the treacherous humidity, the lazily hanging mosses.

Personally, I was most surprised when I ran over a crocodile with my rented bike.

My first trip to Key West was supposed to be a weekend in Maine. It was my birthday and I was excited to return to Acadia National Park… but then rain happened. When my traveling companion glanced at the radar and delivered the bad news, I asked how far the green splotch on the map went – Vermont? Wet. Cincinnati? Soaking. Virginia Beach? Damp, at best. Well, then, where did the giant green splotch end?

“Charleston,” he replied.

“Charleston,” I said, tasting the distant city on my tongue. “So we drive to Charleston,” I said, “and we see how far we get.”

Well, we made it to Charleston in time for a delicious cup of morning coffee and doughnuts, and, with the wanderer’s creed of “just a bit farther” we continued to Savannah, St Augustine, Miami … and Key West. A mere spur-of-the-moment 1,500 miles.

Accommodations:

Miami itself is further from Key West than one might think, 3.5 hours drive without traffic. If there is any traffic, you’re done for, because there is exactly one main road that goes through the islands (route 1, of course). It’s also two hours between the first key (Key Largo) and the final one (Key West) so plan accordingly, especially if you have a flight out of MIA to worry about. Now, for cheaper accommodations, I recommend staying off the final island if possible. Key West is the busiest, most popular, and most expensive of the chain. Do visit but you may not want to stay there. As for options, AirBNB is a good bet and there is at least one hostel in Key West though I have not been there. Many hotels and B&Bs will include bonuses like free fishing pole and tackle, kayaks, and bikes with stay. Drink more water than you think you’ll need, wear bug spray, and beware the heat.

Things not to miss:

Snorkle and scuba dive – If you come to this island paradise with any interest in diving, DON’T MISS IT. If you’ve never been snorkling and you can swim, I highly recommend giving it a try. It’s some of the most exciting diving on the planet. You put your face in the water and it’s like watching National Geographic. For around $40 per person, you can join a diving group for maybe four hours out on the water. It’s fantastic. One other pro tip- don’t forget to reapply your reef-friendly sunscreen every few hours. The water can act like a magnifying lens, frying your back as you paddle merrily along, which you won’t be feeling for several hours (and oh boy, then you’re going to feel it for sure!)

If you’re not hitting the reef and you still need sun care, check out “Sun Bum” sunscreen. It’s in many beach shops there and California and if you don’t mind spending a little extra, you, too, can smell like a very expensive banana (and you’re going to need their cooling lotion if you missed that last tip about reapplying sunscreen!) Overpriced? Almost definitely, but like the scent of “Sex Wax”, it instantly transports me to warm beaches and endless sun, which in February is much cheaper than a ticket to Orlando!

The Hemmingway House is absolutely worth a visit if you’re a book nerd, manly man, or cat fanatic and The Green Parrot exists for those who still need more of a “Papa” fix. My own favorite hobby is walking through town, admiring the stately colonial architecture, and peaking into the lush pocket gardens full of mangroves and tropical flowers. Naturally, you also need to spend time on the beach. Walking (or biking) over Seven-Mile Bridge if you’re hardy enough is unforgettable because visibility allows you to see every fish scooting along the sand beneath you. Chartered water sports in Key west (parasailing, paragliding, boat charters and rentals) are also cheaper than almost anywhere else in the US.

Lastly, a quirky piece of Americana in the restaurant Better than Sex. Like Madame Puddifoot’s in the Harry Potter movies, Better than Sex is designed as a date spot. If you found a hot date on your trip (or imported one with you) bring them here to this dessert-based placed for naughty-themed cocktails and the best chocolate grilled cheese of your life. Now, just because it’s a date place doesn’t mean this can’t just be a giggle-worthy time with a good friend or a very special moment between you and your cheesecake. No one will judge in this candle-lit atmosphere so thick you can barely see your delicious meal. Each time we go, the ambiance gets darker- this last time they gave up entirely and swapped the paper menus for Ipads.

Eat some conch fritters and key lime pie, have a good margarita, listen to live music, do some water sports, check out the crazy sunset parties on the beach, and…

Oh, did you think I forgot the secret I said I’d tell you?

Here it is: when you get to Key West itself, Duval street is the main area and “party town”. There are all kinds of art galleries and tchotchke stores on Duval. There is also a Starbucks.

Near sunset time, go into this Starbucks, sneak out the back door into the Hotel, and go straight into the elevator on the other side. Head to the top floor. Stay sneaky. Hum “Mission Impossible” if that helps.

Wah-la. You are in one of the best and highest places in town to grab a drink and watch the sunset over the whole city. They frequently have live bands playing and they fix a mean cocktail.

Have you been to Key West lately? Did I miss anything important? What’s the farthest you’ve gone on a spontaneous road trip? Tell me in the comments.