The Florida Keys, stretching approximately 120 miles long, has plenty to offer from private getaways, to vibrant nightlife and seaside adventures including scuba diving, fishing, and boating. My favorite places to stay are Islamorada and the last of the keys, Key West.
Islamorada – Island of the Purple Sunset
The Florida Keys stretch for miles off the coast of southern Florida. Islamorada has been one of my favorite keys to visit when I want some time in the sun (away from winter overnight shoots in NYC) and desperately need to get some scuba diving days in. About 30 to 40 minutes south of the more well known Key Largo, its smaller town feel and lack of packed tourists is what attracts me to this place. And yes the sunsets are pretty amazing.
Overseas Highway 1 is the only major road that stretches from Key Largo at the base of Florida all the way down to Key West, the final key where Earnest Hemingway spent some time living and writing. From end to end, the drive is somewhere in the ballpark of about 4 hours, but well worth it just to stare out the window at the palm trees, the expansive ocean on either side of the highway, and to feel the tropical breeze.
Unlike the closer Key Largo, Islamorada has less larger store and restaurant chains. Less people in general. Instead, the roadside entices you in with signs for more mom-and-pop style knick knack shops and local owned diners and specialty restaurants. Most places serve pretty good seafood and there’s a nice mix family friendly places or the more party oriented Tiki bars.
Islamorada – Favorite restaurants and places to hang
I like food of all kind. When it comes to breakfast though, I love the Midway Cafe for its delicious coffees, variety of omelettes, and other baked goods. Also the decour in this place is popping with color and the design feels like a more hip roadside country inspired home. If you’re looking for more of a Diner environment then Mangrove Mikes Cafe is your stop. Attached to a gift shop with all sorts of nautical inspired knick knacks, it’s a fun place to browse while waiting to be seated or after filling your belly.
Although pretty much every restaurant I’ve eaten at has pretty great seafood, from fish dishes and conch soup, to gator bites, one of my favorites is Lazy Days. While not the fanciest of places, I like sitting waterfront on the sand when I can get a table. The food and staff has always been great here.
The Keys don’t have sandy beaches. Mostly due to the reefs (that protect the shores from erosion) that are one of the main attractions for divers. However the Islander Resort has a wide man made beach for laying out in the sun, and is one of very few places I found down there that lets you come enjoy their pool and bar side without needing to be an actual guest of their property. Meaning if you find a hotel for cheaper without those amenities, you can always take a drive to the Islander to hang poolside.
As with many other hotels, they have an on site adventure shack where you can rent small sailing vessels (they do lessons) Wave Runners, and all sorts of water toys. For small boats, as in you and 3 buddies just want to drive a boat around, snorkel, fish, whatever, I like the deals and folks at A1A Watersoprts and Boat Rentals.
If you’re up for a DJ, (some nights) And a good old fashioned Tiki Bar that prides itself on frozen drinks and Rum Runners, the one at the Postcard Inn is pretty great. Not to mention, the daytime snack bar on the water, and nighttime fire pits, where you can sit and stare at the moonlight kissing the ocean with that special someone, are pretty great as well.
Key West – The End of the Road
While sadly I didn’t get to spend much time in Key West personally, the drive down was well worth the trip. Unlike the rest of the keys, Key West opens up into a much larger town. Instead of the long stretching highway where the community is either left or right of you on the highway, Key West offers plenty of little side streets and residential areas to explore.
Although there are tons of food options for every taste, I made a quick stop at a little hole in the wall called Fritas Cuban Burger Cafe and I’m glad I did. Although more known for the Frita, a heart stopping, mouthwatering cuban take on a burger, I had a few empanadas (my food weakness) and they were delicious.
A quick stroll down the famous Duval Street exposed a vibrant selection of both restaurants and other shops selling clothing and artwork made by locals. One of my favorite sights was practically a literal hole in the wall where a seemingly off the boat old cuban man (who seriously reminded me of my grandfather) sat in an old wooden chair hand rolling a few cigars. The man had character and reminded me of my own family like him. The last of his generation.
Scuba Diving – My Favorite Shop
I love Scuba Diving and wish I did it more often. With several trips to the keys and a few dive operators (not all great) my favorite group of folks is Key Dives in Islamorada. The staff is great and their boat, the Giant Stride, is always clean. I love their attention to personal instruction and the fact that they send every trip with a guide (for those of us that still suck at navigation).
While I won’t name the shops I don’t like because maybe they just had a bad day while I was with them, I will say Key Dives has been consistently fantastic and I highly recommend them for Divers of all skill levels. They’ve also encouraged and helped me out everytime I’ve brought my Canon 5D3 down in its beefy Ikelite housing. They helped me spot all kinds of sea creatures and made sure to point out some great photo ops even above water I may not have considered.
While the Florida Keys, are bigger than what I have had a chance to see in my few trips, it’s a place I keep going back to and am always happy to discover something new even while I visit some the more familiar places. I hope this helps if you’ve ever considered going or are planning a trip anytime soon.
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