“Island-hopping to land’s end, this one-of-a-kind highway offers the promise of radiant seascapes, exotic underwater worlds, and animals found nowhere else in America.” Such praise for Florida’s famed Overseas Highways––in Reader’s Digest coffee table book The Most Scenic Drives in America, no less––inspired me to rent a car in Miami and drive to the Florida Keys this May. I am grateful I did. 

The drive from North Key Largo to Key West, the southernmost tip of the continental U.S., spans 42 bridges, hundreds of hotels and restaurants, and countless options for ocean-fun under the sun.


As someone who has sought out the world’s most scenic drives––from Scotland’s Isle of Skye to British Columbia’s Sea-to-Sky Drive, from Ireland's Ring of Kerry to Italy’s Amalfi Coast––I would definitely recommend the Overseas Highway, with the following two caveats.

One, don’t expect a feeling of remote isolation. Two, embrace the island lifestyle. You won’t be alone on Overseas Highway, and you shouldn’t be in a rush. The one-lane highway (several stretches do include passing lanes) runs from island to island––or key to key––and is surrounded by countless bars and restaurants, terrific watersports, arguably the best fishing in North America, and a contagious vibe of island fun specific to the laid-back, friendly Florida Keys

Key Largo

Roughly 30 miles long and just two miles in width, Key Largo is the largest of the Florida Keys. For a cool view of its geologic underpinnings, stop at mile marker 103 on Rte 1, where an expanse of coral has been exposed on the bank of a man-made channel. An outstanding spot for snorkeling and scuba diving is John Pennekmamp Coral Reef State Park, an undersea wildlife preserve.


According to the International Game Fish Association (IGFA), more saltwater fishing records have been set in the Florida Keys than anywhere else in the world. Islamorada is the heart of the Keys when it comes to fishing. 

“Where else in the world can you go out in the morning and catch a 300-pound swordfish and a 30- or 40-pound dolphin, come back in to catch a few snappers for dinner, then in the evening go out and catch a 100-pound tarpon?” asked Andy Newman, Media Relations Director of Newman PR.

Word to the wise: When visiting Islamorada, even if you’re just driving through, make a point to stop at Lorelei Restaurant & Cabana Bar. Failing to do so, will be a mistake. Cheap drinks, live music every night, fantastic yet inexpensive seafood and spectacular sunsets are all part of the experience. Click here to see my full article on this gem of a restaurant. 

Also, I’d be remiss if I didn’t mention two guides based out of Islamorada’s Bud N’ Mary’s Marina. The first is Nick Stanczyk, son of fishing legend Richard Stanczyk who’s owned Bud ’N Mary’s since 1978. Nick and his family discovered a school of broadbill swordfish off the coast of Islamorada and pioneered the current approach for daytime swordfishing.

The second is Jim Willcox, who’s been named one of the top five fishing guides in the world.


Two years ago I spent a day fishing the Everglades with Willcox and have to say it was the single best experience I’ve ever had with a guide. 

Long Key State Recreation Area

A great spot to stop if you want the classic adventure of canoeing or kayaking in the Keys. This 1,100-acre park offers variety of self-guided nature trails, including one that was designed for exploration by canoe––enjoy the mangrove-fringed lagoons and tropical hammocks. 


My wife and I enjoyed two very unique, family friendly attractions at Marathon. The first is The Turtle Hospital, a small non-profit dedicated to the rehabilitation of endangered sea turtles.

This one of a kind “hospital” offer regular tours of the facilities, and you can observe sea turtles they are currently nursing back to health. They also do special release parties when they re-introduce a sea turtle back into the wild.   

The second place we spent an afternoon at was The Florida Keys Aquarium Encounters. This is a place kids will love, but so will adults. You get to pet sting rays, swim with hundreds of colorful fish, watch 300-pound goliath grouper eat, and feed sharks by hand.



If you're hungry yourself, they also have tasty paninis and a variety of other food at the Eagle Ray Cafe. 

Little Torch Key

This small island is the launching pad for one of the elite island resorts in the world. Lucky guests access Little Palm Island Resort & Spa by riding a 1930’s style motorboat from Little Torch Key.

Upon arrival at the 5.5-acre island, guests are pampered beyond belief at a verifiable paradise island featuring 15 thatched roof bungalows, private beaches, outstanding food and high-scale amenities ranging from sailing to scuba diving to spa treatments.

My 3-night stay at Little Palm Island was an incredible highlight

Key West 

Key West is the end of the road, the southernmost tip of the continental U.S. Much to the delight of its locals and visitors, the island embraces its reputation as an eccentric, wacky, barefoot and carefree bohemian island town. It’s a real melting pot of U.S., Latin American and Caribbean culture … and the views aren’t bad either. 

The island, with its signature Duval Street lined with entertainment and island excitement, was rightfully featured in the New York Times-best seller “1,000 Places to See Before You Die.” If you’re looking for a place to stay in the heart of it all, treat yourself to a night at Ocean Key Resort & Spa.  


In sum, the Florida Keys would make anyone’s bucket list of places to see, and I can’t wait to again cruise Overseas Highway. 

For more information on things to do in the Florida Keys, visit Fla-keys.com.