This Is the Ultimate Road Trip From Miami to Key West
Say Sayonara to South Beach
Get ready to put the Magic City in your rear view mirror. While the sizzling sands of South Beach and its 24/7 energy always provide a good time, we’re changing latitudes in favor of the ultimate island-hopping adventure. It’s Key West or bust.
Fuel Up in Homestead
Before we hit the Overseas Highway, it’s all family-owned farms, orange groves, and strawberry fields in rural Homestead. Instead of whizzing on by, stop at Knaus Berry Farm where you can load up on homemade cinnamon rolls (the ooey-gooey kind), lip-smacking good milkshakes, and u-pick strawberries.
Follow in Flagler's Footsteps
U.S. Route 1 turns into the Overseas Highway right before you get to Key Largo. This stretch of coastal roadway is labeled by mile markers (hence the “MM” in each of the addresses) and retraces the route Henry Flagler used to construct the Florida East Coast Railway in 1912. Be on the lookout for old railway sections that run parallel to the Overseas Highway.
Explore a Coral Reef at a State Park
Located in Key Largo, John Pennekamp Coral Reef State Park is a mostly undersea park that spans 70 nautical miles. Check out the view from the shore, or strap on your snorkel gear and swim through magnificent coral reefs and schools of tropical fish. Park admission starts at $8 per vehicle.
Dive a Sunken Ship in Key Largo
Originally launched in 1955, the USS Spiegel Grove served as an official vessel for the United States Navy for many decades. It was intentionally sunk in 2002 to help construct an artificial reef in the Florida Keys National Marine Sanctuary. Today divers can explore the 510-foot shipwreck through charter services like Island Ventures in Key Largo. Excursions start at $85 per person.
Shop Local Art in Islamorada
Art abounds in Islamorada. Don’t miss the monthly Third Thursday Art Walk hosted by the Morada Way Arts & Cultural District. Or visit The Rain Barrel Artisan Village where you’ll find everything from paintings and sculptures to jewelry and glass designs.
Stop at the Sportfishing Capital of the World
Islamorada is likely home to the highest density of professional fishing guides in the world. Book a fishing charter with one of the captains at the Lorelei Marina, but make sure you get back in time to swap stories at happy hour. Or skip the fishing altogether and sip tasty rum concoctions at the bar.
Feed the Tarpon at Robbie's Marina
Grab a bucket of baitfish and dangle them right above the water on the docks at Robbie’s Marina. Soon you’ll see swarms of giant tarpon ready to scarf down a snack. Although the signs say not to feed the pelicans, they sure do fight to get in on the action.
Swim with the Dolphins in the Lower Keys
Catch a ride on Flipper’s dorsal fin at the Dolphin Research Center, a not-for-profit education facility in Grassy Key. The center rescues and rehabs dolphins, sea lions, and manatees. General admission is $28 for adults and $23 for kids. Dolphin encounters start at $199 per person.
Save a Sea Turtle in Marathon
The Turtle Hospital, the world’s only licensed veterinary hospital dedicated to sea turtles, has rescued and released more than 1500 turtles since its founding in 1986. Learn more about these endangered swimmers and learn what you can do to help. Admission is $22 for adults and $11 for kids.
Scout the Seven Mile Bridge
Walk, run, or bike the scenic Seven Mile Bridge in Marathon. This is the best place to actually set foot on a portion of Henry Flagler’s old railway. While you’re there, explore Pigeon Key, a five-acre island and former work camp for the Florida East Coast Railway that’s listed on the National Register of Historic Places.
Kick Back on a Beautiful Beach
Consistently recognized as one of the best beaches in the country, Bahia Honda State Park is pure paradise. Head out on a snorkeling tour of the Looe Key National Marine Sanctuary or spend the day soaking up some rays on that sugary white sand. Admission is $8 per vehicle.
Watch for Key Deer on Big Pine Key
Did you know that the endangered Key deer, which are about the size of a medium sized dog, are found in the lower Florida Keys and nowhere else in the world? Look for these beautiful creatures along the highway (and make sure to slow down!) or try to spot them on the nature trails at the National Key Deer Refuge on Big Pine Key.
Snap a Selfie at the Southernmost Point
Once you’ve made it all the way to eclectic Key West, commemorate the journey with a photo op in front of the concrete buoy at the Southernmost Point. This landmark is located just 90 miles from Cuba. But don’t call it quits yet; you’ve still got one more stop ...
Celebrate at Mallory Square in Key West
It’s time for a celebration of epic proportions and what better spot to relish the best road trip ever than the nightly sunset dock party at Mallory Square. Watch as local performers and artisans put on quite the show as the sun sinks into the ocean. Perhaps a barhopping adventure along Duval Street is next? Congrats on making it to land’s end!