The Ultimate Florida Keys Road Trip

Embrace the laid-back Keys life on a classic drive down the Florida Keys Overseas Highway (U.S. 1). The roughly 100-mile (one-way) route island-hops along the southern rim of the Everglades and Florida Bay from Key Largo south to Key West. Featured stops celebrate all things Keys: fresh-caught seafood, old-school roadside attractions, and unspoiled state and national parks. While the Keys largely have bounced back from Hurricane Irma, recovery efforts continue in some areas. Before hitting the road, check the Florida Keys & Key West website for updates.

Key Largo

Key Largo is the Gateway to the Florida Keys. Ease into the Keys like a local by detouring east off U.S. 1 (south of Homestead) and onto Card Sound Road (CR 905). Before crossing the Card Sound Bridge to North Key Largo, stop for conch fritters at Alabama Jack’s, an old-school Florida beach bar. Continue the vintage vibe with a canal tour (reservations required) aboard the African Queen. The restored steamboat—made famous in the 1951 classic movie of the same name—is docked at Marina Del Mar (Mile Marker 100). Take a deep dive into Key Largo’s natural side at John Pennekamp Coral Reef State Park (Mile Marker 102.5), the nation’s first undersea park. Book a snorkeling tour to explore one of the park’s shallow (averaging five to 15 feet deep) inner reefs. For deepwater views without getting wet, take a glass-bottom boat tour to Molasses Reef, located about six and a half miles offshore. Consider taking an Everglades tour in Key Largo for a classic Florida adventure: a wet and wild airboat tour in Everglades National Park.

Eat and Stay: Mrs. Mac’s Kitchen and Playa Largo Resort & Spa

Islamorada

Drive south across the Tavernier Creek Bridge (Mile Marker 91) and you’re officially in Islamorada. Widely known among anglers as the “sportfishing capital of the world,” the village of Islamorada is made up of Plantation Key, Windley Key, Upper Matecumbe Key, Lower Matecumbe Key, and the offshore Indian Key and Lignumvitae Key state parks. Stop at the Rain Barrel Artisan Village (Mile Marker 86.7) to browse the jumble of shops in the back and snap an Instagram pic of the 30-foot-high Florida spiny lobster out front. In the Morada Way Arts and Cultural District (Mile Marker 81.6), tour the art galleries and sip an Iguana Bait or other microbrew at the Florida Keys Brewing Company. Try a slice of honest-to-goodness gold—not green—key lime pie at the cozy Midway Cafe and Coffee Bar (Mile Marker 80.5). At Robbie’s Marina (Mile Marker 77.5), choose your favorite way—boat, canoe, Jet Ski, kayak, or SUP—to play on the water.

Eat and Stay: Green Turtle Inn and Pines & Palms Resort

Marathon

Located about an hour south of Key Largo and an hour north of Key West, the 10-mile-long Marathon island chain is the approximate midpoint of the Florida Keys. On the drive from Islamorada south to the city of Marathon (Mile Marker 59.9), stop at Long Key State Park (Mile Marker 67.5) for bird-watching, hiking, and snorkeling. To get out on the water, rent a boat or kayak from All Aboard Boat Rentals (turn left at Mile Marker 54.5). Get up-close views of sharks, rays, and other local marine life; take a marine biologist­–led tour (included with admission); and even go snorkeling in a 200,000-gallon saltwater tank (extra fee) at Florida Keys Aquarium Encounters (Mile Marker 53), slated to reopen in mid-December. Schedule a 90-minute, behind-the-scenes tour of the Turtle Hospital (Mile Marker 48.5) to help support the facility’s sea turtle rehabilitation efforts.

Eat and Stay: Brutus Seafood Market & Eatery and Tranquility Bay Beach House Resort

Lower Keys

Seven Mile Bridge, the Keys’ most famous and longest bridge, links Marathon (Mile Marker 46.75) to the Lower Keys (at Sunshine Key, Mile Marker 40). Driving the east-west span delivers 360-degree water views—Florida Strait to the east and Gulf of Mexico to the west—typically reserved for boaters. To see the crystalline green-blue waters, wait until daylight to cross the bridge. Approaching Big Pine Key (Mile Marker 33), the largest of the Lower Keys, slow down and follow posted speed limits to protect the Lower Keys’ endangered key deer. Stop at the National Key Deer Refuge visitors center (check website for current hours) for directions to wildlife viewing areas such as the Blue Hole and Watson/Mannillo Trails. Glide through mangrove trails looking for dolphins, tropical birds, and other wild things on a Key West Eco Tours guided kayak or paddleboard backcountry tour. The two-hour trips depart from the Geiger Key Paddle Hut at Geiger Key Marina (Mile Marker 10.5).

Eat and Stay: Boondocks Grille & Draft House, Ramrod Key, and Parmer’s Resort, Summerland Key

Key West

Continue southwest on U.S. 1 to its southern terminus, Mile Marker 0 in Key West. On the way, stop in Stock Island to go snorkeling with Namaste Eco-Excursions at Stock Island Marina Village (left at Mile Marker 5) or rent a kayak or SUP at Lazy Dog (Mile Marker 4.2). In Key West, park at Old Town Garage in the Historic Seaport. Walk or ride the Old Town Trolley to get around. Buy a one-day tour pass to hop on and off the trolley near must-see attractions, such as the Custom House, the Key West Butterfly & Nature Conservatory, and the Ernest Hemingway Home & Museum. Take the requisite selfie at the Southernmost Point Buoy, marking the southern tip of the continental United States. For the best views in town, climb 88 steps to the top of the historic Key West Lighthouse, people-watch at Mallory Square, and take a “Red Sails in the Sunset” cruise aboard the Jolly II Rover tall ship. From Key West, retrace your route north on U.S. 1 to complete the trip.

Eat and Stay: Thirsty Mermaid Raw Bar and Restaurant and the Gardens Hotel

Maryellen Kennedy Duckett lives, writes, and drives the backroads in East Tennessee where she wakes up curious every day. You can follow her on Twitter @mekd.