If you love driving, year-round balmy weather, delish seafood and discovering historic sites, motoring through the Florida Keys is a vacation experience you will treasure.
This coral cay archipelago starts around 15 miles south of Miami and includes five major regions: Key Largo, Islamorada, Marathon, Big Pine and Lower Keys and Key West. The island chain, which stretches over 120 miles, is linked by the “Scenic and Historic Coastal Highway” named The Overseas Highway or A1A, which starts in Key West and runs north over the Atlantic Ocean, Florida Bay and Gulf of Mexico and up to Georgia. A key attraction to the area is the tropical Caribbean-like climate that has two seasons: 1.) Hot/wet June to October average temps 90 °F. 2.) Dry season November to April, average temps 75 °F. Fly into Miami, take this scenic journey heading south, and you can fly out of Key West to many destinations. So, grab your sunglasses, find your car keys, start your engine and explore…
The Northern Keys
Start your trip in Islamorada (pronounced I-la-mo-rada).
In this picturesque village of six key Islands, set between the saltwater boondocks of Everglades National Park and the deep blue waters of the Florida Strait, beach life is king. It’s a tourism-oriented community known as the Sport Fishing Capital of the World. The scenic bay, ocean views, boating, fishing, quaint restaurants, shops and galleries attract tourists by the thousands.
Stop by the marina venue Robbie’s of Islamorada, it sits right on a beach. Feed fish to the tarpon on a dock. Shop at outdoor souvenir shops and dine at the Hungry Tarpon Restaurant and Bar. There’s a roof, no walls and expect iguanas to saunter up to your table looking for scraps. Try the Conch Ceviche, Trailer Trash Burger and Broiled Spin Lobster Tail.
A bright aqua blue and yellow exterior makes Islamorada Brewery & Distillery easy to spot on Route A1A. Take a tour of the distillery, indulge in beer or rum tastings and sip on the tangy citrus-flavored Islamorada Ale. COVID made IB&D expand to a spacious backyard with a food truck (go for the Churrascaria Menu) and their craft beer and cocktails are now sold to-go.
The sign outside reads Chef Michael’s Peace, Love & Hogfish restaurant, which verifies a Chef Michael Ledwith specialty. It’s Hogfish, which is indigenous to the area, looks like Red Snapper, but is meatier, flakier, sweeter and tastier. This is one of the most elegant, white-cloth-table dining experiences in the entire Keys. Start with the Petite Lionfish “Creole” Flash Fried, then the delectable whole Hogfish and end with the five-layer Carrot Cake.
Middle Florida Keys
Head south to the enclave of Duck Key.
The primary reason for venturing to Duck Key is a stay at the very plush AAA Four Diamond Award–rated Hawks Cay Resort. Pick from lush hotel rooms with balconies to spacious three-bedroom villas. Roam the 60 acres on foot or in a golf cart then make your first stop wading into the unique Saltwater Lagoon that’s surrounded by sand and perfect for safer swimming. People-watch at the lively main pool scene that has a d-jay, or for a quieter experience lay out at the Oasis Cay adults-only area. Paddle boarding, kayaking, diving, jet skiing, sunset cruises, fishing expeditions and dolphin encounters will appeal to your adventurist side.
The resort’s most sought-after dining experience is the indoor/outdoor restaurant Angler & Ale. View the dramatic Hawks Cay Marina vista as you dig into Whole Fried Snapper or Grouper Cheeks. Bring the fish you caught that day, and under the ‘Hook N Cook’ option, the chef will broil or fry it for you. As you drink some Angler’s Ale brew and bite into their delicate Key Lime Pie you’ll discover why reservations are at a premium.
Drive on to Marathon and visit its 13 islands, beaches and barrier reef.
Bring your turtle diary.
In Marathon, Loggerhead Turtles famously nest at Coco Plum Beach and to learn more about their fascinating lives, you can visit the Turtle Hospital, which opened in 1986 to treat the injured sea creatures and return them to the wild. Join an enlightening guided tour and gaze at loggerhead, green, hawksbill and Kemp’s Ridley turtles.
Swimmers and sunbathers tend to love the narrow, quiet Sombrero Beach and the Curry Hammock State Park sandy shoreline and mangrove creek. History buffs like to check out the Adderley House, in the Crane Point Historic and Archaeological District. It’s a Masonry Vernacular house built in 1906 by George Adderley, a black Bahamian immigrant. Or visit the Pigeon Key Historic District, for the eight frame vernacular structures built between 1909 and 1920 as a railroad construction work camp for Black laborers on the “oversea railroad.”
For a flavorsome Cuban lunch, stop by King Seafood – Market & Restaurant. Fresh fish caught daily from local fishermen is on the Latino menu. Dine on a Minuta (Cuban style fish Sandwich). Munch on butterflied, boneless Whole Snapper (skin & tail on) and end with the very cheeky Fried Key Lime Pie.
Road trip over 42 Bridges. Marvel at The Seven Mile Bridge—the big daddy.
It’s like skimming over water.
A drive through the Keys heads over 42 bridges. The majestic looking Seven Mile Bridge starts at Knights Key, a southern section of Marathon in the Middle Keys, and ends on Little Duck Key in the Lower Keys, on the way to Key West. The box-girder, white structure, made with prestressed concrete viaduct arcs up to 65 feet, so boats can pass under. But lots of the bridge barely skims the water and that’s the fun part. Drive on the famous bridge pictured in Licence to Kill and 2 Fast-2 Furious and it’s like you’re motoring across a bridge in a movie. The Knights Key-Pigeon Key-Moser Channel-Pacet Channel Bridge that runs parallel to SMB was built in 1912. This historic “oversea railroad” trestle no longer functions and is now a tourists’ promenade.
Discover the Most Famous Key
End your journey in the lively island city of Key West.
Key West, the county seat of the entire Monroe County, is just 90 miles off the coast of Cuba and is to Florida what New Orleans is to Louisiana. It’s a party capital oasis that attracts international tourists who go sunbathing, swimming, shopping and sightseeing during the day, and bar/restaurant-hopping at night. The town is distinguished by its 19th and 20th century architecture, with conch houses lining quaint palm-tree lined streets that were introduced by African heritage immigrants from the Bahamas.
To get a feel for the city, board a Conch Tour Train. Pull out your camera and let the narrated, humorous mini-train ride around the city school you on the facts and figures of the most lauded historic venues. Check out: Harry S. Truman Little White House, Key West Aquarium and Mallory Square, which is an ideal location for KW’s famed sunsets. Survey Bahama Village, a 16-block, diverse area that’s a lasting vestige of the Afro-Caribbean people who settled in the vicinity in the 1800s. Today, if you visit the Bahama Village Market, you’ll hear reggae, calypso and rhythmic junkanoo music. And you must have a photograph taken at the iconic Southernmost Point Buoy, which marks the most southern point in the continental U.S.
You can rest your head at the very chic Winslow’s Bungalows by Kimpton Key West, just blocks away from lively Duval Avenue where tourists love the clubs, restaurants and shopping. This string of 85, exquisite bungalow guest rooms, with three pools set among lush verdant foliage, is an oasis within an oasis. No central hallways, instead guests enjoy private entrances, porches, on-site parking, free continental breakfast and a helpful staff that makes this hotel feel more like a lush retreat.
10 Must Things to do in Key West
Walk, drive or bicycle to these famous spots and you’ll create the memories of a lifetime.
- Wear a bright shirt to Key West Butterfly & Nature Conservatory and beautiful, winged creatures may land on you.
- Walk around the historic grounds of Key West Lighthouse & Keeper’s Quarters (circa 1848).
- View the six-toed cats and famous author’s mansion at Ernest Hemingway Home & Museum.
- Listen to jazz music and sip wine on the romantic Sunset Sail With Sebago Key West.
- Sunbathe at Fort Zachary Taylor Historic State Park Beach for its serenity, Higgs Beach for the lively bar-scene and Smathers Beach for the longest stretch of sand in the city.
- Eat Crab Cakes and Oxtail at Mo’s Restaurant, a Haitian-owned, black-business Creole eatery.
- The famed signature Swordfish dish at the tony Bagatelle Key West restaurant is genius.
- The taste and crunchiness of the Fish Sandwich at Caroline’s Key West will make you smile.
- Black History’s imprint on Key West is evident in venerable churches, stately cemeteries, public parks and an American Legion Hall dedicated to black veterans of WWI and WWII.
- Play tennis at Higgs Beach Park Tennis Courts and get instruction from Tennis Key West.
Get behind the wheel of your auto, a rental car, a pink Cadillac, Little Deuce Coupe, Beamer or Benz… and explore The Keys from the road on a memorable adventure.