The Florida Keys, the Southernmost point of the continental United States, are a string of coral islands tracing south from Miami 160 miles to Key West. The name Key is derived from the Spanish cayo, which means “small island” – a word originally borrowed by Spanish explorers from the native Taino Indians of Hispanola and Cuba.
The famed Overseas Highway follows Route 1 from Miami to Key West on a beautifully scenic drive that is consistently heralded as one of the top US road trips to experience in your lifetime. And for that reason, shortly after Christmas, we flew down to Miami and embarked on a weeklong adventure through the Florida Keys.
About halfway between Miami and Key West lies Islamorada. Home to a dozen or so resorts, as well as many great restaurants, Islamorada is a great home base for the first half of your Keys road trip.
Where to Stay
The Keys definitely have a low-key beach vibe and for that reason I wasn’t really looking for 5-star luxury here. I wanted to stay somewhere that truly evoked the spirit of the Keys and we found that in La Siesta Resort & Marina. We splurged a bit for our room which was a 1-bedroom cottage with a living area and kitchenette, opening directly onto the beach – oddly named “Mango Cottage,” despite its purple color. In addition to the beach and pool, we also loved how this hotel offered complimentary bikes, kayaks and paddleboards to all resort guests!
Where to Eat
- Lazy Days – delicious fish, right on the beach
- Morada Bay Cafe – come early to get a spot beachside in time for sunset
- Midway Cafe – great for breakfast and lunch. And don’t miss the original Manny & Isa’s key lime pie!
- Green Turtle Inn – Dating to 1947, the establishment was originally made famous for serving up sea turtle delicacies.
- Hungry Tarpon – Located at Robbie’s Marina; casual waterfront dining
Where to Drink
- Holiday Isle Tiki Bar – Based at The Postcard Inn, a sister hotel to La Siesta, you can ride your bike over to enjoy the original “Rum Runner” cocktail
- Islamorada Beer Co – a local brewery offering tasting flights
- Florida Keys Brewing Co – another great local brewer with tasting flights and a backyard “beer garden”
What to Do
- John Pennekamp Coral Reef State Park – a great place to snorkel or scuba in Key Largo (unfortunately our scuba trip was cancelled due to high winds!)
- History of Diving Museum – tons of information and memorabilia on the history of diving and the evolution of gear in the sport
- Robbie’s Marina – for a few bucks you can buy a bucket of fish and feed the giant tarpon that frequent Robbie’s Marina – just watch out for the pelicans!
- Kayak & paddleboard – The Keys are all about water sports
- Ride bikes – a great way to get around without worrying about traffic or parking
Continuing on to Key West, it’s definitely worth making a few stops along the way to see some local wildlife…
- The Turtle Hospital – in Marathon, you’ll find a sea turtle rescue hospital that has rehabilitated and re-released thousands of sea turtles since opening in the 80’s.
- National Key Deer Refuge – Many people don’t know there are deer in the Florida Keys, but the Key Deer Refuge is home to the diminutive species of Pine Key Deer. They are elusive, but you may find alligators and other wildlife as you walk through the trails.
Continuing to the very end of the archipelago, you’ll arrive at the largest city, Key West – located just 90 miles north from the island of Cuba.
Where to Stay
There are a ton of hotels to choose from in Key West, but given that it was New Year’s and Key West can be a bit of a rowdy town, we chose to stay a bit outside the downtown area on nearby Stock Island. The Perry Hotel Key West opened in 2017 and is set right on a marina with a fabulous pool and lots of great spots to hang, dine and drink. I just love the design focus and chill laid back vibes of this hotel.
Where to Eat
- The Breakfast Club, Too – Great breakfast – no surprise there! I closed out 2018 with some epic chocolate chip pancakes and cinnamon sugar butter – yum.
- Little Pearl – A little off the main drag, this cute restaurant is perfect for date night.
- Matt’s Stock Island – Located at The Perry Hotel. Solid brunch and nice shareable plates for a lighter dinner.
- Salty Oyster – Poolside bar with casual eats at The Perry; happy hour is great deal with 50% off food and drinks.
What to Do
- Ernest Hemingway Home & Museum – Located in Old Town Key West, this historic building was home to Ernest Hemingway from 1931 to 1939. Designated a National Historic Landmark in 1968, descendants of Ernest Hemingway’s famed six-toed cats still call the property home. I recommend joining one of the regular tours that start every twenty minutes or so.
- Duval Street – The main drag in Key West, home to lots of dive bars, cafes and shops. Great for people watching.
- Southernmost Point Buoy – Pretty self explanatory but a popular photo op.
- Sunset Celebration in Mallory Square – Starting 2 hours before sunset every night, head to Mallory Square to see the sunset and enjoy the sunset celebration featuring street performers, food carts and drinks to go (no open container laws in Key West!)
- Jet Skiing with Key West Water Tours – Several tour operators offer jet ski trips around the island of Key West. We really enjoyed that this one was guided and included brief stops with history of the locale (in addition to going really freaking fast). This was a blast and I highly recommend it!
In short the Keys are the perfect place for an easy getaway where you can enjoy sunshine, water sports, history, and casual dinners of fresh fish beach side – an ideal equation to unwind and rejuvenate for the new year to come!
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