Road trip: The quirky, cool Florida Keys

Note: All travel is subject to frequently changing governmental restrictions—please check federal, state and local advisories before scheduling trips. This post was updated May 18. 

Start thinking about rolling the windows down and blasting your favorite Jimmy Buffett tunes. You’ve been inside too long and now it’s time to start planning the ultimate road trip through the quirky, cool Florida Keys for when the 120-mile island chain is fully open again. Getting there will be half the beauty since the the Keys are connected by the unforgettable Overseas Highway, where the Atlantic Ocean lies on one side of the road and the Florida Bay and the Gulf of Mexico on the other. No other road offers breathtaking vistas like this—all open sea and sky. It’s just what you need after spending so much time at home. Just be sure to call ahead to make sure all the hotels and attractions mentioned here are open and ready for business.

Plus: Here are 15 things you shouldn’t say to a Miamian if you want to avoid the heat.

The Overseas Highway represents a remarkable engineering feat, as stretches of roadway and 42 bridges leapfrog across the water from key to key in a series of giant arches of concrete and steel. Sometimes called the Highway that Goes to Sea, the road follows a trail originally blazed in 1912 when entrepreneur and railroad baron Henry Flagler completed the extension of his Florida East Coast Railroad from Miami to Key West. While the railway was severely damaged after a hurricane in the 1930s, the highway’s foundation includes some of the original railway columns. It’s truly a site to behold.

To help you navigate your adventure, you’ll want to take note of the mile markers on the right shoulder of the highway. These green markers bear white numbers and descend in order from 127 to 0, ending up in the southernmost city. Without further adieu, here are a few of the best places to check out from Key Largo to Key West and everywhere in between.

1. Go snorkeling and sip tropical cocktails in Key Largo.

After snorkeling through colorful schools of fish and sunken treasures in the crystal clear waters of the John Pennekamp Coral Reef State Park, hang out at the Pilot House Restaurant and Glass Bottom Bar. Located in the heart of Key Largo at mile marker (MM) 99.5, this waterfront hotspot is a great place to sip on a cocktail and enjoy the view. Try the Pilot House Punch made with several kinds of rum, guava juice, grenadine and cranberry.

2. Listen to live music and nosh on the best slice of Key Lime pie you’ve ever had in Islamorada.

Photo courtesy of Kara Franker

Live music, stunning sunsets, gorgeous water views . . . what more could you want from a cabana bar in the Florida Keys? Visible via a towering blonde mermaid situated along the roadside at MM 82, the Lorelei is a favorite for Islamorada locals and tourists alike. No matter what you do, don’t leave this waterfront oasis until you’ve sampled a slice of the Key Lime pie. It’s probably the best we’ve ever had. And the fish tacos are delicious, too.

3. Feed the tarpon and watch the pelicans fight for a piece the action at Robbie’s Marina.

Photo courtesy of Kara Franker

Grab a bucket of bait fish and head out onto the dock at Robbie’s Marina located at MM 77.5 in Islamorada, for a family-friendly adventure you’ll never forget. Giant (and we mean huge; these fish can grow anywhere from 4 to 8 feet long) tarpon swim beneath the docks and they’re waiting for you to dangle that little fish in the water for a yummy snack. These mammoth fish will compete with pesky (but oh so cute) pelicans for that tasty meal. Technically you’re not supposed to feed the pelicans and they can get a little aggressive, but oh man, they’re quick on the draw! And the experience makes for great vacation photos.

4. Explore one of Florida’s best beaches at Bahia Honda State Park.

Photo courtesy of Kara Franker

Featuring a picture-perfect white sand beach and aquamarine water, Bahia Honda State Park at MM 37 on Bahia Honda Key is a pristine tropical paradise. You could easily turn this pit stop into an entire day of fun in the sun. Climb to the top of the Old Bahia Bridge for breathtaking views. The bridge spans the 5,055-foot channel and was part of the East Coast Railway built by Henry Flagler between 1905 and 1912. A road was built on top of the railway as party of the original Overseas Highway, but use of the bridge stopped in 1972. How’s that for a Florida history lesson?

5. Toast to the sunset and the best road trip ever at the Sunset Pier in Key West.

Photo courtesy of Kara Franker

Congrats, you’ve made it to the end and mile marker 0! Celebrate with a toast at the Sunset Pier, the best seat in town for Key West‘s infamous sunset celebrations. Located between Key West Harbor and adjacent to Mallory Square, Sunset Pier is part of the luxurious Ocean Key Resort, but it’s open to the public whether or not you’re staying at the hotel. Order a mojito or whatever cocktail you fancy and enjoy the show.

Tagged: Florida