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Road Trip Through the Laid-Back Florida Keys

by Gregory D. McCluney

Mar 5, 2020


March 2020

KICKING BACK IN KEY WEST and the Florida Keys embodies the definition of days off for busy business travelers and visitors on holiday … and a permanent state of mind for residents. If you arrive by air, Key West International Airport is as laid-back as any in the United States. If you make the 160-plus-mile drive from Miami, the views will surely begin your decompression, and the same goes for passengers on the ferry boats cruising the straits from Miami.

With 800 islands in this archipelago, you’ll never see them all. The only highway, U.S. 1, touches only about 10 percent of them. If you choose to drive, plan to spend some time exploring some of the islands along the way. Key Largo, one of the first you’ll come to, hosts the famous Caribbean Club where Bogie and Bacall filmed the movie Key Largo in 1951. Still serving, it provides a perfect introduction to the atmosphere, food and cocktails ahead on the Overseas Highway to Key West.

If you’re interested in sea life, visit John Pennekamp Coral Reef State Park, a great place to snorkel over one of the only live coral reefs in the United States. If traveling with the family, visit the dolphin encounter for a swim with these remarkable animals. There’s also a wild bird sanctuary that displays the Keys’ native birds, many under rehab care by local volunteers for their injuries. If it’s time for a meal, stop by Key Largo’s famous Conch House for a taste of conch fritters, the origin of the Keys’ “Conch Republic” slogan.

Heading south from Key Largo, Islamorada dubs itself the sportfishing capital of the world. While some might disagree, this island does host several full-service marinas with every fishing experience visitors might like to try, from group fishing to individual private charters costing $1,000 a day and more. This key is all about the water and the sports that thrive on and under it. To take it all in in one location, stop at Robbie’s of Islamorada, where you can see all the boats for rent, check out the dive boats and shop for the charter that fits your budget — and then browse an open-air market.

This marina also runs trips to two remote islands — Indian Key Historic and Key Botanical state parks — if you’re interested in what the Keys looked like before all the development. After your trip back in time, head to Upper Matecumbe Key, where you’ll find a cluster of shops, bars, fish restaurants and accommodations to fit any budget and taste.


Continue south (and west) past Layton and you arrive in the Middle Keys. In Marathon you can visit a favorite beach of the locals, Sombrero Beach, as well as the terminal for Island Hoppers Aerial Adventures. This offers a chance to see the Keys from the air and spot the best beaches and reefs, an experience visitors and their families will never forget. You might even spot a shipwreck. Families can also enjoy a visit to the turtle rescue hospital on Vaca Key. For a low-key lunch amid beautiful grounds, drop in to Hawks Cay Resort on Duck Key.

Next up: the famous Seven Mile Bridge (over water) and on to the Lower Keys and Key West. During a stop at the National Key Deer Refuge on Big Pine Key you may spot a small Key deer grazing or maybe an alligator in the fresh water of the Blue Hole. You’ll find more diving opportunities here, including a shipwreck. Looking for luxury? Try the private island experience of Little Palm Island Resort & Spa, accessible only by boat. For families, many less expensive lodgings are available.

A short drive west takes you to the main attraction of any visit to the Keys: Key West, the town itself. Depending on how much kicking-back time you have and your interests, a good place to start is the Conch Tour Train. This touristy ride will show you the most popular sites and provide a bit of history. Old Town on Duval Street presents a self-guided walking tour of restaurants, bars, clubs, galleries and even a butterfly conservatory. Many visitors prefer to stay in Old Town at some hidden gems such as the Marquesa Hotel or the Eden House. But if you prefer a waterfront location, check out the Southernmost Beach Resort or the Westin Key West Resort & Marina.

Bike rentals, abundant and inexpensive, offer a good way to get around to see The Ernest Hemingway Home and Museum (don’t miss the six-toed cats), the Audubon House & Tropical Gardens, Key West Lighthouse and the Schooner Wharf Bar overlooking the Key West Historic Seaport. The Mel Fisher Maritime Museum proves popular for all its nautical treasures. More active visitors and families will find options everywhere for diving and snorkeling, kayaking, hiking nearby islands and sportfishing. Just 68 miles west, you can dive and explore the wrecks and ruins of Dry Tortugas National Park, including Fort Jefferson, established in 1846.

Sunset draws visitors and locals alike to Mallory Square for the special nightly celebration. This tradition is part carnival, part street food and drink with live music, and part natural sensation you don’t want to miss. Or if you have another sunset in your schedule, choose from several options to sail the local waters with full buffets, drinks and even a dance floor. Another possibility: Just enjoy a catamaran sail with open bar.

Dinner means selecting from the plethora of every possible cuisine imaginable as you walk the menus on Duval Street. For a big night out and something special, head to Michael’s Restaurant or Café Solé. On your way home, Duval Street will just be warming up. Nightlife, restaurants and entertainment options abound in Key West, much less so as you navigate the Keys back northeastward on the Overseas Highway (U.S. 1) to Key Largo and the mainland.

For LGBTQ+ visitors, Key West remains one of the premier destinations in the United States and beyond. Two annual events attract LGBTQ+ visitors from around the world: Fantasy Fest, a 10-day celebration of all that is gay in Key West, and PrideFest, usually held in June. Popular clubs include the 801 Bourbon Bar, where you can play drag queen bingo; the Aqua Bar and Nightclub, presenting drag queen shows; and the Bourbon Street Pub, featuring male dancers and a clothing-optional garden bar. Virtually all restaurants welcome everyone. For an overview, hop on the Gay Key West trolley tour for a tour of bars, shows, popular gay and lesbian accommodations, and a bit of history of gay life in the Keys.


Choose from four ways to reach Key West and other towns among the 800 islands that separate the bay side (Gulf of Mexico) and Atlantic Ocean side, the Straits of Florida. Most business visitors arrive by air into Key West International Airport or Miami International Airport, where they rent a car and drive one of the most scenic drives (about 160 miles) in America. MIA provides the most air service, both domestically and internationally, but most major U.S. airlines and some smaller commuter services fly direct to Key West. There you can find taxis, shuttles and rental cars. The airport lies just a few miles from the city center and Duval Street.

Greyhound provides bus service from Miami. Some visitors take the ferry from Miami to Key West and either stay over or return to Miami that night. Ferry service also runs from Florida’s west coast, seasonally.

Parking can be a challenge if you drive yourself or arrive during the high festival seasons. If you bring a car, check with your hotel regarding parking options.


This historic resort boasts the only private beach in Key West plus pools, gardens, golf, spacious suites, business services and a fitness room, all with ocean views. Guests enjoy access to The Reach Resort and its spa.

1500 Reynolds St., Key West

A sprawling resort near the beach includes pools, several restaurants and bars, a marina for water activities and conference facilities. Great for families, with rooms and suites for groups away from the crowds. Don’t miss the resident dolphins.

61 Hawks Cay Blvd., Marathon, Duck Key

Get a taste of private island life at this five-acre paradise with 30 oceanfront suites and no phones or TVs. Reopening in April, it includes private beaches, pools, spas, gourmet food and water activities. Arrive by boat or seaplane.

28500 Overseas Highway, Little Torch Key


French goes Caribbean where Chef Correa raises the bar on fine dining in style. Dine inside or out and enjoy classics like duck à l’orange or fresh mutton snapper in pesto, plus authentic key lime pie.

1029 Southard St., Key West

If it was a slow day for fishing or you just crave some prime beef with all the trimmings, Sixty- One delivers a big-city beef emporium to the tropics in a stylish, upscale business setting.

Hawks Cay Resort, 61 Hawks Cay Blvd., Marathon, Duck Key

Eat and drink like Hemingway where he hung out with friends. Dating back to 1933 (the end of Prohibition), the original saloon moved to Duval Street in 1937. Enjoy live music, dancing, a solid menu and cold beer.

201 Duval St., Key West


FX Excursions

FX Excursions offers the chance for once-in-a-lifetime experiences in destinations around the world.


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