For those of you joining us for the winter months in Florida, a short drive down Highway One, often called the Overseas Highway, delivers you to the “other-worldly” Florida Keys. From Key Largo to the north down 113 miles of coral and limestone islands connected by 42 bridges, (one is seven miles long), to Key West and the southern-most point of the continental United States, the mileposts along the way reveal a host of spectacular beaches and water treasures, a full array of quirky and fun bars and restaurants, and more sightseeing and tour adventures than you’ll ever find time for.
Don’t let the overly commercial and cluttered main drag of Highway One discourage you. The real treasures are often just off the main road, tucked away in live oaks, mangroves and lush gardens.
Building your itinerary for a Florida Keys adventure.
Our recent trip from Bonita Springs, Florida down to the Keys was truly a delight. Our itinerary was greatly aided by a recent article in the January issue of Southern Living magazine which offered many unique spots to explore not often found in expected travel sites. There are numerous other resources to map out your trip to the Keys to find lodging, dining, recreation and other activities. Check out Trip Advisor, AirBnB, (who wouldn’t want to stay on a private house boat in a remote and quiet lagoon?), as well as the many Florida Keys tourism and travel sites.
A short diversion to the remarkable South Beach in Miami.
For our journey from SW Florida, we decided to include a stop on South Beach in Miami. It had been over twenty years since we had been there and we were anxious to revisit the palm-lined beach and historic district, the Art Deco hotels and condominiums and the many great restaurants for a quick lunch before continuing on to the Keys.
Despite terrible traffic all through Miami and out to the beach, the slow crawl to Highway A1A and South Beach was well worth the time. We started with a walk down the storied beach during a somewhat cooler day for South Florida, so it was less crowded than normal, (though 70’s felt pretty good to this Michigan couple). If you’re there, check-out the long stretch of lifeguard towers spaced all down the beach, each a different color and unique architectural style.
The Art Deco buildings alone make this trip worthwhile. Art Deco is a style of visual arts, architecture and design that began in France in the early 1900’s and can now be found in iconic buildings around the world like Rockefeller Center in Manhattan, and of course, South Beach Miami. You will be craning your neck upwards as you walk the many blocks of the historic district to take in and photograph these beautiful buildings.
Next stop in Islamorada, the “Village of Islands”.
From Miami, we began the journey south, stopping first around Mile Marker 80, in the village known as Islamorada, a renowned fishing mecca. Fair warning, lodging all down the Keys is expensive and often difficult to find if you don’t book early. We stayed at the vintage Chesapeake Beach Resort on the Atlantic Ocean side, unfortunately with much reconstruction underway from Hurricane Irma; still a pleasant and hospitable place to overnight.
At Southern Living’s recommendation, we visited the Florida Keys Brewing Company to sample some local brews. Located in the Morada Way Arts and Cultural District which houses a handful of shops and galleries, the brew pub featured a tropical outdoor beer garden and live music.
That night we dined at tables outdoors on the sand overlooking the back bays of Islamorada at the Morada Bay Café with wonderful views, ambiance, food and beverage. It was comfortable and casual dining, but very good. The sunset was spectacular. There is a more formal and upscale restaurant, Pierre’s, right next door with equally marvelous views.
Check out the ALLTHE ROOMS Vacation Rentals Lodging Guide at https://www.alltherooms.com/vacation-rentals-islamorada
… and on to Key West.
We set off early the next day for the end of the chain of Keys in Key West, traveling through many scenic islands including Marathon and Big Pine Island. Our first stop in Key West was Smathers Beach on the south coast of the island. Who says the Keys don’t have great beaches! This is a terrific spot for sunning and strolling, snorkeling and water activity rentals like kayaking and Hobie Cat sailing
A guided tour of Papa’s house.
We headed “downtown” and made our way to the famed Ernest Hemingway home on Whitehead Street. The house was built in the mid-1800’s by local sea captain, Asa Tift and has survived multiple hurricanes over the past decades. For Hemingway fans, our guided tour was an incredible experience as you learn more about the writer, his family, (and four wives), and the 55 cats that make their home there, all descendants of Hemingway’s first cat, a six-toed (Polydactyl) white cat named Snow White. The cats remain a popular feature of the house tour and many joined our tour group as the guide led us room-to-room.
As a writer and novelist, I was personally moved to see “Papa’s” writing studio, still furnished and equipped much as it was in the ‘30’s when Hemingway penned some of his most famous classics like “To Have and Have Not” and “The Old Man and the Sea”. Don’t miss it!
We unloaded our beach cruiser bikes and began a riding tour through the shady streets of Old Key West. For lunch, we found Eaton Street Seafood Market and enjoyed wonderful takeout of grouper sandwiches and salads, sitting under the umbrellas watching Key West’s colorful collection of souls stroll by.
Sloppy Joe’s a “must-see”.
Any trip to Key West would be incomplete without a stop at the infamous Sloppy Joe’s bar and restaurant, one of Hemingway’s regular drinking holes. Sipping on cold Corona’s, we listened to a local guitarist sing a great selection of popular hits, including of course, the obligatory Jimmy Buffet offerings. You find yourself in a bit of a time warp as you imagine sitting at the bar where decades ago the great writer entertained friends and visitors with his many stories and antics.
Reluctantly saying goodbye to Key West after continuing our beach cruiser bicycle ride through the old historic district, Truman’s Little White House and the Truman Annex and down along the docks, we headed north to the mid-Keys. On Big Pine Island we managed to find the remote “No Name Bar” on the north side of the island. (Make sure to have a good GPS on board!) and enjoyed a cold beverage and very tasty fish dip. You can add your signed dollar bill to the many thousands stapled to every square inch of wall and ceiling.
For dinner, we found ourselves at Keys Fisheries overlooking the bay and docks as the day’s fresh catch was brought in. They have a wonderful raw bar upstairs for fresh shrimp, crab and oysters.
In all, a great excursion to one of our country’s most beautiful stretches of water and landscape. In a couple of days, we only scratched the surface of the many highlights of the Florida Keys, but we are already considering plans for next winter to take the boat ferry out of Naples directly to Key West for another visit. We hope you enjoy your next trip to the Keys as much as we did.
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