Stretching 120 miles off the southernmost tip of Florida, the Florida Keys are known as a mecca of watersports, relaxation, and a welcoming place for alternative lifestyles. During a road trip down from Miami with my family in February 2018, I was fortunate enough to see some of the best the archipelago has to offer. Here’s my list of recommended stops on your Caribbean road trip.
Grab Drinks at No Name Pub and Visit Betsy
While remnants of Hurricane Irma damage were still present at the time of my trip through the Keys, I was amazed how quickly some popular stops managed to pull themselves back together. As someone who loves any dose of old-school Americana, Betsy the Giant Lobster on Islamorada is the perfect place to stretch your legs and snap a kitschy photo. Touted as the largest anatomically correct lobster sculpture in the world, it’s just too weirdly iconic to pass up the five-minute pit stop. Continuing around 50 miles down Highway 1, you’ll hit Big Pine Key. Don’t forget to grab a cold drink at No Name Pub. Serving locals since 1936, it’s the oldest bar in the Keys. In the 1970s, patrons also began tacking dollar bills to the walls inside. The tradition continues today, so be sure to leave a bill of your own!
Take a Tour of the Hemingway Home
There’s plenty to do and see once you reach Key West, the final island in the Keys. One of my first stops was the Ernest Hemingway Home (with very appropriate apparel I might add). Fairly self-explanatory, the Spanish Colonial-style home on Whitehead Street was built in 1851, and later remodeled by Hemingway in the 1930s. It was his primary residence until 1940. Unique features of the home include the island’s first in-ground pool, a collection of European furnishings, and a population of Hemingway’s odd six-toed cats that still roam the grounds. Tours of the house and gardens, which include an in-depth exploration into its history and Hemingway’s Key West, run everyday between 9 a.m. and 5 p.m. Note that tickets can’t be purchased in advance, and are payable by cash only.
Snap a Picture at the Southernmost Point
A quick stroll from the Hemingway Home is the Southernmost Point monument; geographically the southernmost point of the continental United States. Marked by a large, painted buoy since 1983, it’s also roughly 90 miles away from Cuba. The monument was also recently refurbished in late 2017 after sustaining damage during Hurricane Irma. One of the most photographed landmarks in the country, there’s hardly a time when there isn’t a crowd waiting for a photo-op. The best advice I can give is to be patient and be quick. (This is not the time for a full-on photo shoot.) Aim for a clear day, and you won’t be disappointed with the results.
Stop by Key West’s Oldest Home
Located on the famous Duval Street, the Old Island Restoration Foundation maintains a museum of the oldest residence on the island. Built in 1829, the home functions as a comprehensive resource for visitors who want to learn more about the history of the island, and what life was like for Key West’s early residents. The museum is free to the public, except Sundays and Wednesdays. The interior of the home showcases period artifacts and furnishings, with a staff on-call to answer any questions about the history of the residence. The gardens also contain the only cook house still standing in all of South Florida, plus a pretty entertaining photo-op. It took more than a few tries to get a shot where no one was giggling!
Watch the Sunset at Mallory Square
Without a doubt, one of the best places to catch the sunset on Key West is at Mallory Square. A tradition beginning in the 1960s, the waterfront public space welcomes the end of each day with a two-hour celebration of eclectic variety. Entertainment ranges from local musicians to, much to my initial surprise, sword swallowers. Amidst the colorful chaos, tourists edge their way towards the water to secure an optimal viewing place. My best advice is to arrive early and avoid setting up camp near a performer. Their main goal is to attract attention, so it’s best to put some space between you and the nearest juggler if you want a more peaceful experience. The only thing left to do is sit back and enjoy the show. There’s nothing really quite like a Caribbean sunset!