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Vacation to Florida in the Summer? We Say Yes!

Summer is here, and the open road is calling! With warm weather, blue skies and miles of lush scenery to enjoy, Condé Nast Traveler, in partnership with Booking.com, is officially calling it road trip season. Here’s why you should hit Florida’s Overseas Highway.
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Courtesy espiegle:GettyImages

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Route: Miami to Key West

Estimated Distance: 160 miles

Total Drive Time: 3.5 hours

For those who think that a summer vacation in Florida seems counterintuitive, we have two words for you: air-conditioning. Yes, the beloved invention that allows you to control the climate of your personal space is one of the main reasons why summer is such a popular season for road trips. And if you opt to carve a route through South Florida, making your way from Miami to Key West mainly via Route 1, you’ll never be too far from a beach, either, as you’ll be tracing the Atlantic Ocean to the east and the Gulf of Mexico to the west. (They don’t call it the Overseas Highway for nothing.)

While the drive itself can be accomplished in one nonstop shot, to do that would be missing the point entirely. The 113-mile stretch of highway that takes you through the Florida Keys is awash in outdoor activities, from sunbathing to animal-gazing to fishing to SNUBA® (yes, SNUBA). Plus, being that the summer months are off-season for the Keys (save for a few popular summer festivals, which draw bigger crowds), you’ll practically have the place to yourself.

Starting Point: South Beach

Your trip begins in Miami, home to cutting-edge artists in Wynwood, first-class shopping in the Design District, and a skyline full of pastel-hued Art Deco beauty in South Beach. Fuel up with a cup of joe from the small-batch roasting masters at Panther Coffee, with locations in Wynwood, South Beach’s Sunset Harbour, and Coconut Grove. If there’s a picnic in your future (and there should be; more on that later), stock up on goodies at La Sandwicherie, a no-frills sandwich bar that whips up French-inspired sandwiches and salads in South Beach and Brickell nearly 24/7 (both locations are open until 5 a.m. daily), and slathers them in an addictive French vinaigrette.

A milkshake from Robert Is Here

Courtesy Suna Photography

Second Stop: Homestead

Thirty miles south of Miami, Homestead is where the drive to Key West really begins, and where big-city backdrops are replaced with small-town charms. Case in point: Robert Is Here, a family-run fruit stand that began on this very spot more than 50 years ago, when the titular owner (then six years old) stood on the corner hawking cucumbers from his dad’s farm. Today, it’s an always-buzzing fruit stand and farm with a picnic area, splash park, and live music on weekends—not to mention being a local institution. Also: They make a mean milkshake!

For a more grown-up beverage (provided you have a designated driver, of course), there’s Schnebly Redland’s Winery & Brewery, Miami’s first commercial winery—and like none you’ve ever visited before. Because instead of grapes, these wines are made from exotic fruits like mango, lychee, guava, even avocado. Weekend tours, which last about 30 minutes, conclude with a stop in the tasting room; there’s also an on-site brewery for tropical-flavored suds lovers.

Third Stop: Key Largo

Rather than hopping right onto Route 1, seasoned motorists turn onto Card Sound Road and head straight for Key Largo’s Alabama Jack’s, a roadside beach bar where bikers, retirees, and families all happily comingle and everyone is ordering the conch fritters.

Less than 15 miles away, you’ll pick up Route 1, your home for the rest of this scenic drive. That’s where you’ll find John Pennekamp Coral Reef State Park, America’s first undersea park. Opened in 1963, it comprises 70 nautical miles of gorgeous coral reefs, seagrass beds, and mangrove swamps, is home to hundreds of species of tropical fish, and can be explored via kayak, canoe, paddleboard, glass-bottomed boat, scuba dive, or snorkeling tour.

Movie buffs will appreciate a photo op with the original vessel featured in the classic Humphrey Bogart/Katharine Hepburn film The African Queen. It sets sail daily from Key Largo’s Marina Del Mar marina. (Diehard Bogie fans may want to plan a return visit in October, when Key Largo hosts the Humphrey Bogart Film Festival.)

Hemingway House

Courtesy Rob O'Neal Photography

Fourth Stop: Islamorada

Fishing enthusiasts will want to spend some time in Islamorada, known as the sport-fishing capital of the world. Whether you’re looking to hook a tarpon or simply feed one, Robbie’s is a one-size-fits-all marina where fishing, snorkeling, kayaking, shopping, and, yes, tarpon-feeding (you can buy a bucket of baitfish for $3) are all on the marquee. As is eating at Hungry Tarpon Restaurant, a seafood shack that serves breakfast, lunch, and dinner (go for the fish sandwich—grilled, fried, or blackened).

For those who want to explore the deep sea without getting wet, the History of Diving Museum houses the world’s largest collection of documents, photographs, and artifacts relating to the history of the water sport, including a replica 17th-century diving bell, armored diving suits, and a massive display of helmets.

Have a picnic lunch and give your legs a stretch with a stroll along Anne’s Beach, at Mile Marker 73. The area is made for afternoon lazing, with a swimming area, boardwalk, and picnic tables. If it’s closer to dinnertime and you’d prefer a white tablecloth to a paper one, Pierre’s offers picturesque sunset views and French-fusion-inspired seafood-leaning dishes.

Fifth Stop: Duck Key

Speaking of fusion: Let us introduce you to SNUBA®, your new favorite hybrid water sport, available at Dive Duck Key. Short for “surface nexus underwater breathing apparatus,” it’s a combination of snorkeling and scuba that requires neither a diving certification nor any heavy equipment, yet lets you dive 20 feet below the water’s surface.

Animal lovers will find much to coo about the further south you go: In Grassy Key, the Dolphin Research Center puts you up close with these amazing animals. Dozens of bottlenose dolphins, plus a handful of sea lions, exotic birds, cats, and iguanas call the education and research facility home. For 30 years, The Turtle Hospital in Marathon has been working to improve the lives of sea turtles. As part of their educational mission, they host daily tours of the hospital and its rehabilitation area, where guests can feed the adorable residents.

Amara Cay Resort

Courtesy Juan Fernando

Sixth Stop: Big Pine Key

Hungry again? Take a step back in time at The Wooden Spoon, a roadside diner where patrons fill up on breakfast and lunch comfort food staples like pancakes, burgers, country-style steaks, and homemade biscuits. Equally laid-back, but a little less wholesome, is the No Name Pub in Big Pine Key, a historic restaurant and bar that once also operated as a brothel (long time ago—we promise). Grab one of the outdoor picnic tables and order up a signature pizza, which makes for great road food.

Also in Big Pine, the National Key Deer Refuge protects the lower Keys’ population of Key deer, an endangered species unique to the area. Of the refuge’s more than 9,000 acres, much of it is open to visitors for observation (in addition to the deer, the refuge is a sanctuary for nearly two dozen other endangered plant and animal species).

Last Stop: Key West

Drive another 30 miles and you’ve reached the southernmost portion of the U.S.—colorful Key West, which both Tennessee Williams and Ernest Hemingway once called home. Even if you’re not a fan of popular tourist attractions, or hate The Old Man and the Sea, no visit to Key West is complete without seeing The Ernest Hemingway Home & Museum, if only to glimpse one of his famous six-toed cats. Less than a mile away (a mere 15-minute walk) is the Harry S. Truman Little White House, the residence-turned-museum that served as the former president’s winter home (among the artifacts on display are Truman’s official logs, which fascinatingly detail his comings and goings).

After all that time spent driving, Key West’s very walkable layout means you can ditch the car and wander on your own two feet, with Duval Street as the main drag. Art collectors will appreciate the island city’s unique collection of galleries, like The Key West Art Center, a nonprofit gallery that showcases the work of Florida artists, and The Key West Art & Historical Society, another nonprofit, which preserves the area’s history through a collection of more than 25,000 postcards, photographs, paintings, and beyond.

A room at Ocean Key resort

Courtesy Ocean Key Resort & Spa

When hunger strikes, Key West delivers with a variety of worthwhile dining destinations in its four square miles. The Keys’ oldest eatery, Pepe’s Cafe, still manages to pack in patrons more than a century after first opening its doors (it’s a particularly popular breakfast spot, as diners can build their own breakfasts and accompany them with fresh-squeezed mimosas and screwdrivers). Banana Cafe is another popular (read: often-crowded) spot that serves French-inspired dishes, including a dozen different crêpes. For a more stick-to-your-ribs kind of meal, Charlie Mac’s has got smoked and slathered barbecue fare.

Key West is famous for its bar scene, which can be on the rowdy side, particularly if you stick to its most (in)famous drinkeries like Sloppy Joe’s, Hog’s Breath Saloon, and Captain Tony’s Saloon. But quieter places do exist. The Porch, a craft beer and wine bar, is one spot locals wouldn’t mind keeping a lid on. Part restaurant, part entertainment venue, Turtle Kraals features a waterfront dining room, rooftop bar, bocce court, and live turtle races.

No visit to Key West is complete without a slice of Key lime pie, and Kermit’s Key West Key Lime Shoppe has some of the best—and not just in pie tins, but dipped in chocolate, mixed with strawberry, and turned into jams, cookies, candies, and beyond.

Little Palm Island

Courtesy Little Palm Island Resort & Spa

Where to Stay Along the Way:

Everything about the Amara Cay Resort in Islamorada screams “beach chic”—from the reclaimed wood walls and stylish papasan chairs in the lobby to the rattan accents and furnished private balconies in every guest room. Among the beachfront boutique resort’s unique amenities are a bocce court, shuttle service within a four-mile radius, and the poolside Sparrows Rum Bar.

In a sea of independently operated lodgings, sometimes a familiar brand can be comforting. Enter Hyatt Place Marathon/Florida Keys, a 125-room beachfront property that’s surrounded by some of the area’s most picturesque attractions, including Sombrero Beach (where you’ll find, and want to photograph, Sombrero Key Light), Pigeon Key, Seven Mile Bridge, and the Crane Point Museum and Nature Center. There’s plenty to keep guests occupied on-site as well, with two restaurants, two bars, and a pair of outdoor pools.

It takes a little planning and one extra mode of transportation (seaplane or boat, the choice is yours) to get to Little Palm Island Resort & Spa—but it’s worth the effort. Located on a private resort island just off the coast of the Keys, Little Palm Island embraces its remote location by catering to travelers who want to disconnect, which means no telephones, TVs, clocks, or even kids allowed. With only 28 thatched-roof bungalows available, you could actually spend days here without encountering another guest.

The Marker Waterfront Resort in Key West offers the best of both worlds: While it’s centrally located near the Key West Historic Seaport in Old Town, it’s set just far enough away to feel like a quiet tropical oasis. Opened in December 2014, the 96-room luxury hotel is the first newly built property to open in the city in 20 years, yet it embraces the past with a design scheme that mixes tropical luxury with modern style. Ramble around the hotel’s lush grounds long enough and you’re bound to find one of its three swimming pools or the Mexican-style Cero Bodega restaurant and bar, where tequila is meant to be sipped and savored, not downed by the shot.

Perfectly situated on Duval Street in Key West, right by Mallory Square, the rooms at Ocean Key Resort & Spa are a seamless reflection of the nature that surrounds them, with brilliant shades of teal and private balconies that, in many rooms, offer unobstructed views of the Gulf of Mexico. It all adds up to a welcoming island vibe, which is only enhanced with tropical-inspired bites and beverages at Sunset Pier, an outdoor entertainment oasis that juts out into the water.

Click here to see more guides to The Best of Summer Travel.