My Perfect Day in Key West
Key West is a lazy place meant to be explored at the most leisurely of paces. It is not meant to be conquered with a map and long list of tourist spots to check off the list. It is a place to relax, go with the flow, and if you stumble across something interesting (or air conditioned) along the way…bonus points!
Even though Key West is a tiny island, the heat and humidity slow my explorations so much that I have still not explored all its beauty after nearly a dozen trips. I do not approach Key West in the same aggressive tourist style I use in most other destinations; here, the tropical climate slaps me in the face, turns me into a soggy sweaty mess, and forces me to slow down and get on island time. But in my mind, in the mild climate of San Diego as I write this, all the following activities are possible in one day!
First things first…a girl needs a sweet ride! I have done a lot of research on the topic and have declared Island Safari to have the cutest and most colorful bikes on the island. They will try to give you a basic red or blue one displayed out on the sidewalk, but if you ask nicely, they will take you to a giant garage/warehouse/candy store out back to pick out whatever color you like. Or you can be
lazy practical and just rent a bike from your hotel.
Now, prepared with my wheels……
My favorite place to start the day is Cuban Coffee Queen. They used to have just one location, a tiny stand with only one or two benches outside, but now they have a second (and larger!) location more centrally located on Duval in Key Lime Square. This now breaks my general rule of thumb of “do not eat on Duval Street.” Cuban sandwiches and Cuban bagels are pretty great here, but the pièce de résistance is their iced coffee made with coffee ice cubes. GENIUS! When your ice starts to melt in like 12 seconds in the Floridian heat, at least your coffee will not be diluted!
The original Cuban Coffee Queen also happens to be across the street from another great breakfast place, Pepe’s. You know, so you can spice it up a bit on day 2. A lot of visitors (and locals) rave about breakfast at Two Friends, but I fail to see what the hype is about; I recommend Old Town Bakery instead.
After breakfast, I’ll pop in to Fastbuck Freddie’s Furniture store to mentally decorate my imaginary tropical Victorian mansion….and to soak up some air conditioning.
Then, I’ll meander the side streets in a most inefficient manner towards Fort Zachary Taylor Park. I go up and down and occasionally backtrack as I admire the beautiful homes with their Victorian architecture, whimsical paint schemes, and tropical landscaping. I might even pop into my favorite boutique, Besame Mucho, to admire their gorgeous and well curated goods and surreptitiously cool off in their air conditioning. This really is a great little shop and feels like shopping in a museum; it is worlds away form the tourist trinkets you’ll find on Duval Street, and I almost always buy something lovely here.
Back on the road, I’ll pay my admission fee to Fort Zachary Taylor and pedal towards the fort. There is also a beach here, popular with the locals, but it is not beautiful…..it is typically covered in seaweed and a little smelly. No thanks.
There is a snack bar at the beach here, but I prefer to head back to Old Town for lunch at 5 Brothers Grocery. Just as it sounds, it is a small grocery store, but they have a deli that does not disappoint. You can get your order to go, or eat it standing up at the counter (where there is AIR CONDITIONING). Eaton Street Seafood is another tasty lunch option.
By this time, I’ve biked far and wide in the heat. I’ve eaten lots of pork and learned some history over at the fort. I deserve a massage! Ocean Key Resort has a lovely spa, but it comes with resort prices. My back-up is the locals day spa Isle Style; the spa has a fun boutique up front to browse before settling into the amazing courtyard.
While on this side of the island, I head to Louie’s Backyard for a drink before heading back to the hotel to shower off the mixture of massage oil and sweat. Fully showered and refreshed, I am ready for the Key West sunset and nightlife!
Indulge in a pre-dinner cocktail at Berlin’s. As a cigar bar, smoking is allowed here, and the rich leather upholstery and insane air conditioning (they have the best on the island that I’ve found so far!) is a luxurious retreat on an otherwise laid-back and ultra casual island.
Now I head to Mallory Square for Sunset Celebration and try my luck at spotting the elusive green flash (I have never seen it, but you should still try!). What seems like the entire town gathers here daily to watch the sunset, even clapping after nature’s performance! But I don’t want to watch such a magnificent performance empty handed, so I grab a mojito from the outdoor bar at El Meson de Pepe Cuban restaurant, then wander over to the water.
Pro tip: don’t leave as soon as the sun dips below the water and the crowds start to dissipate. Often, the best is yet to come as the skies turn pink. Now slightly drunk and convinced I haven’t missed anything, there are tough dinner decisions to make. I could stay in Mallory Square and eat the combo plate of ropa vieja, picadillo, and plantains at El Meson de Pepe, or venture to nearby A&B Lobster on the marina for a steak (lobsters are creepy). Other dinner favorites for other nights include Santiago’s Bodega, with their extensive tapas menu, local seafood joint Thirsty Mermaid, and the outdoor-yet-classy Michael’s. If you have a car, Hog Fish is a great local option off the tourist path.
An after dinner drink is a requirement in Key West, and The Porch and Caroline’s Other Side (not to be confused with Caroline’s Cafe) are contenders. Then, it’s back to the hotel after making a quick stop for a slice of chocolate covered key lime pie on a stick at the KW Key Lime Pie Company!
Tomorrow is another day. I can sweat all over again!