Travel: Road Trippin’ to the Florida Keys: Celebrating 200 Years of Sunsets

Relax in tranquility at the Hawks Cay Marina. (PHOTOS PROVIDED BY HAWKS CAY RESORT)

On the way to Key West, my husband and I perched atop the Old Bahia Honda Bridge, soaking in the panoramic views below. Swimmers bobbed in the turquoise waters, beach umbrellas added pops of color to the white-sand beach, and teens snorkeled near the shoreline. As part of Bahia Honda State Park, this bridge spanned the 5055-foot Bahia Honda Channel, serving as part of the East Coast Railway that oil mogul Henry Flagler constructed between 1905 and 1912. Built on top of the railway bridge in 1938 as part of the original Overseas Highway (but not used since 1972), the road now provides scenic vistas of the stunning Florida Keys islands.

Since 2022 marks the 200th anniversary of Key West’s first permanent settlement, it seemed the perfect time to make the trek. But that eight-hour drive from Orlando to Key West seemed daunting.
Enter the Florida Keys Road Trip—where the journey is the destination. With 113 miles of Overseas Highway spanning the island chain, you can make pit stops in the Upper, Middle, and Lower Keys. On the way home, build a “sleepover” in Miami Beach—the perfect halfway point between Orlando and Key West.

Follow this road trip itinerary to explore the best of the Florida Keys.

Travelers are delighted by the Coral Cay Entertainers. (PHOTOS PROVIDED BY HAWKS CAY RESORT)

Upper Keys

As you approach Homestead, skip congested U.S. 1 and opt for lesser-known Card Sound Road. As the gateway to the Keys, Key Largo eases you into island-time. Anchor your stay at the amenities-packed Reefhouse Resort & Marina, sprawling across 17 lushly landscaped acres. Recover from the first leg of your road trip with a massage at By the Bay Spa. Next, head to the oversized pool or private beach, as swaying palms and salty breezes lull you into vacation mode. Enjoy a casual dinner at Gus’ Grille, then grab a frozen cocktail at Breezer’s Tiki Bar to watch the sun sink into Blackwater Sound. Cap off the night around the firepit, planning your next day’s adventures such as an eco-boat tour or jet-ski rental from the onsite Pirate’s Cove Watersports.

Known as the Dive Capital of the World, Key Largo offers opportunities to play in, on, and under the water, from stand-up paddle boarding and swimming to fishing and boating. Try scuba diving, snorkeling, or booking a glass-bottom boat tour for an up-close look at the coral reefs and colorful marine life. Head to John PenneKamp Coral Reef State Park to explore on land and sea. Tip: Buy a Florida State Park Annual Pass online a few weeks before your trip. A family pass costs $120 and gives you access to all 175 Florida state parks, trails, and historic sites for one year.

To shop locally, stop at The Rain Barrel, looking for the iconic giant lobster outside. Peruse the store, then step out back for a peek at artisan wares, like hand-painted decor from Amy’s Creations or Key Lime Sugar Scrub from Bella Sol.

Hawks Cay Charter Fishing. (PHOTOS PROVIDED BY HAWKS CAY RESORT)

Middle/Lower Keys

Explore Islamorada to Marathon, with a stay at Hawks Cay Resort as your home base. In Duck Key, the 60-acre property brims with onsite experiences. Dip into five pools, dine at onsite restaurants, play tennis, ride bikes, paddle a kayak, or wind down with a sunset cruise. Don’t miss the Dolphin Connection, providing a mix of education, conservation, and interactive experiences.

The Middle Keys pop with locally owned restaurants, shops, and attractions. The Morada Bay Arts and Cultural District hosts an art walk through its six-block corridor bursting with artisans, eateries, and studio spaces every Thursday. Love craft beer? Sip a cold one fresh from the taps of either Islamorada Beer Co. (try the coconut key lime No Wake Zone) or Florida Keys Brewing Company (go for the solid Spearfish Amber Ale).

Dig into history with a tour of Pigeon Key, “the tiny island under the Old Seven-Mile Bridge.” This five-acre spot served as a camp for 400 workers constructing Flagler’s Florida Keys Overseas Railroad. Its museum now showcases the railroad’s history and residential cottages. Previously accessible only by ferry, a 60-passenger tram now transports visitors along a 2.2-mile bridge span starting this summer.
Stop at the 534-acre Bahia Honda State Park in the Lower Keys for those majestic panoramic views. But venture into the water, too! Rent kayaks or book a snorkeling tour to explore the reefs of Looe Key National Marine Sanctuary. Then savor a fresh-catch dinner at Square Grouper, an eco-friendly eatery in Cudjoe Key.

Catch of the day with Hawks Cay Charter Fishing. (PHOTOS PROVIDED BY HAWKS CAY RESORT)

Key West

Packed with must-see sites, Key West beckons you to linger. Stay at Margaritaville Beach House Key West, a relaxing getaway from the buzzing historic district. Located across the street from Smathers Beach, the resort infuses that chill Jimmy Buffett vibe throughout the property—from margarita-glass chandeliers in the lobby to hammocks and Adirondack chairs sprinkled along its winding paths. Lounge with a frozen concoction by the Fins Up pool, grabbing delicious meals and snacks from Tin Cup Chalice Bar & Chill on the veranda.

Hop on the resort’s complimentary shuttle to the downtown historic district. Go back in time to the Harry S. Truman Little White House (an American history lover’s dream) and Key West Museum of Art & History (in the former U.S. Custom House). Take a deep dive into shipwrecks, pirates, and sunken treasure at the Mel Fisher Maritime Museum. Consider taking a Conch Trolley Tour, where you can hop off to visit the Hemingway Home, stroll through the Key West Butterfly and Nature Conservatory, snap a pic at the iconic Southernmost Point, then grab a beer at the infamous Sloppy Joe’s. Need a break? Dine alfresco at Bistro 245 with magnificent waterside views. While the crowds still head to Mallory Square for the nightly sunset celebration, they have dialed the entertainment down a bit because of the pandemic.

Before embarking on the four-hour drive to Miami, fuel up with authentic Cuban fare from Floridita Food Truck at the funky Havana Cabana resort. Grab a table under the thatched-roof-covered patio and enjoy fish tacos overlooking the largest pool in Key West.

Duck Key Island. (PHOTOS PROVIDED BY HAWKS CAY RESORT)

Miami

Stay at the chic National Hotel in Miami Beach as your trip winds down. In the Art déco Historic District, this oceanfront property sports the area’s longest infinity-edge pool, providing a luxurious end to your road trip. You’re within walking distance of hot spots like Lincoln Road and Ocean Drive. Nearby, the Miami Beach Botanical Garden provides a tranquil escape from the bustle of the city. Back at the hotel, walk to the beach for mesmerizing views of the Atlantic Ocean. Amble along the Beach Boardwalk, a picturesque pathway that stretches for 40 blocks along South Beach. End your trip with a tapas-style dinner at Mareva 1939 on the veranda before, finally, driving home.