A Florida Journey: Road Trip to Key West

Dining waterside at Latitudes at the Sunset Key Cottages, just offshore from Key West, FL, we watched intently as the sun set closer to the ocean horizon. Both inside and at Latitudes’ beachfront outdoor tables, travelers toasted to the lovely moment, a quintessential element of any Florida Keys vacation.

For Luxury Travel Advisor, our dinnertime trip to Sunset Key (reachable via quick boat transport from Slip 29, behind Opal Key Resort & Marina Key West) was a high point of a 350-mile “bucket-list” roundtrip journey into the Keys, from Greater Fort Lauderdale to the road’s end in Key West.

Yes, we savored Latitudes’ lobster bisque, an arugula and radicchio salad, Caribbean lobster tail, Wagyu beef skirt steak, fine wine and that incredible sunset. But that was just one of the moments of discovery on our four-day Florida Keys trip. Here’s a look at our southward drive, with insider tips for luxury travelers. 

Heading South

Officially, the Keys drive begins at the start of the 113-mile-long Overseas Highway, a federally designated All-American Road (US1), connecting the individual islands. Forty-two bridges, including the famed Seven Mile Bridge near Marathon, FL, leapfrog across the water from isle to isle. Today’s modern highway follows the path of the Florida Keys Over-Sea Railroad, completed by industrial railroad magnate Henry Flagler in 1912.

Before its demise following a 1935 hurricane, the railroad carried a half million passengers, but its legacy endured—opening the isles to increased tourism. Look for roadside green-and-white mile markers (MM), the easiest way to find most anything along the Overseas Highway. Most northerly is MM127 at Florida City on the Florida mainland, near the main entrance to Everglades National Park located in mainland Monroe County.

The Keys’ longest and most northerly major island, Key Largo, is the first major stop for many travelers, extending from MMs 107 to 91. Land’s End (as far as the road goes) is Key West, the farthest point south at MM0.

Key Largo

At MM102.5, travelers will discover an eco-jewel, John Pennekamp Coral Reef State Park, part of the massive Florida Keys National Marine Sanctuary and America’s first underwater preserve. To learn more about the eco-system, we’d recommend stopping at the park’s visitor center, which has a 30,000-gallon saltwater aquarium, and offers a 50-minute “Waters of Wonder” movie. Near the visitor’s center, small beach areas attract sunbathers, swimmers and snorkelers. Hikers can head out on marked trails while waterways attract saltwater fishing fans. That said, be sure to read the park’s visible signage about some local residents—crocodilians. One thing is sure, though, John Pennekamp State Park is a lovely scenic spot and definitely worth a visit by travelers.

For many older Americans and movie buffs, Key Largo first gained fame with the 1948 “Key Largo” flick starring Humphrey Bogart, Edward G. Robinson and Lauren Bacall. Movie fans can make a photo stop at MM104, the Caribbean Club Bar, where some exterior “Key Largo” location shots were filmed. Another movie fan stop is at the Holiday Inn complex, Marina Del Mar, MM100, home to the restored, 1912-era African Queen. Yes, it’s the original steamboat from the 1951 movie, starring Bogart and Katherine Hepburn. Listed on the U.S. National Register of Historic Places, the African Queen operates scenic one-and-a-half-hour cruises along Key Largo’s Port Largo Canal. Watch the boat engine’s steam pressure build, listen to its whistle, and if conditions permit, take a turn at the helm. To book a time slot and buy tickets, visit calypsosailing.com.

One fantastic spot for lunch with water views is the open-air, dockside Sol by the Sea restaurant at the Playa Largo Resort & Spa, an Autograph Collection Hotel, MM97. We dined at this rustic, charming spot. Think: Part “romantic beach shack,” part “Bohemian-styled eatery,” but with fantastic views of kayaking, boating and birds. Start with conch fritters, definitely try the seafood mac-and-cheese, and then peruse Sol by the Sea’s menu that includes steamed mussels, fresh fish, a Wasabi tuna burger, plus meat and chicken dishes, too. 

The Sol by the Sea restaurant at Playa Largo Resort & Spa
The Sol by the Sea restaurant at Playa Largo Resort & Spa is a romantic beach shack, where one can enjoy dock-side dining.  (Playa Largo Resort & Spa)

Recently added by the resort is an exclusive dinner-time Water Table Dining Experience. Guests settle into Adirondack-like chairs at a table purposely positioned in calm bay waters, then enjoy dinner with their feet in the water and savoring the sunset. Reservations are required. Desire a more adventurous offshore experience? Scuba divers often desire to explore underwater shipwrecks or the famous Christ of the Deep statue, for instance. Chat with concierge Zafram Scott ([email protected]; 305-853-1001).

Overseeing operations at the upscale Playa Largo is Kristine Cox, general manager. Guests choose from 178 luxury rooms and suites, including 10 two-story bungalows and a three-bedroom beach house with a private pool. As for good-to-know “intel,” the resort is home to the Upper Keys’ first ceviche bar, plus guests absolutely love the beachfront hammock pods. For advisors desiring to learn more or discuss specific client needs, reach out to Heather Turkay ([email protected]; 305-204-4050), director of sales and marketing.

Last winter, the property’s ownership also opened the first Playa Largo Ocean Residences, an exclusive enclave of private, three- and four-bedroom vacation home rentals (each 3,600-3,800 square feet). Some are completed, others are still under construction. Guests can choose two layouts—Sea Spray with three bedrooms and 2.5 baths and Sunrise with four bedrooms and 4.5 baths. Each home has open living floor plans, outdoor living areas, charming front porches and much more.

Quirky Sites, Fun Selfies

The Florida Keys has a reputation for independently minded (but friendly) locals and quirky fun sites. Those driving along the Overseas Highway will have plenty of spots to view unique artwork, statues and manatee-shaped rural mailboxes. Definitely pull over at Rain Barrel Village, MM86.7. You’ll instantly spot “Betsy, the Lobster,” a humongous Florida spiny lobster statue that’s 40 feet long and 30 feet high. It makes a great selfie backdrop.  

Also, keep your eyes peeled for the gigantic Conch shell outside Theater of the Sea, the marine mammal park at MM84.4. Much farther south is a large, playful-looking manatee statue, outfitted in red pants and a blue floral shirt; that’s outside the Shady Palm Art Gallery and Photography Studio at MM48.5. Pop into the gallery to see the creative works of 50 Keys artists. 

Luxury and Pampering

We stayed for two nights at the iconic, 27-acre Cheeca Lodge & Spa, 81801 Overseas Highway, MM82. Car valet personnel provided a friendly greeting, quickly parked our car and removed the luggage for transport to our room. Check-in was a breeze as multiple desks were open for quick service and staffers offered a welcome glass of bubbly. While the lodge exudes a casually elegant aura, it delivers a five-star luxury experience on all fronts.

Within minutes of dropping our stuff in our deluxe oceanfront room, we zipped out to the beachfront Atlantic’s Edge (one of three restaurants on site) for a late lunch; it’s known for its prime steaks and fresh seafood, plus it offers views of the beach and the lodge’s private, 525-foot-long pier.

Our spacious “Lodge Oceanfront King Suite” had an open floor plan, good storage, a plush king-sized bed, living area sectional sofa (convertible to a comfortable, queen-sized bed) and a roomy bathroom with large-glassed-in rain shower, vanity with two sinks and a separate toilet closet. Most spectacular, though, was the large, open-air balcony with a private soaking tub and stellar beach, Atlantic Ocean and pier views. 

There are 43 new “Luxury Oceanfront King Suites” or “Luxury Oceanfront Double Queen Suites.” For example, within the 685-square-foot king suite, guests will find floor-to-ceiling glass doors, a large open-air balcony with private soaking tub, a 42-inch flat screen TV and a king bed with premium pillow-top and fine linens. Of course, it also offers a comfortable, well-appointed living area with queen-sized sleeper sofa, an oversized bathroom with deluxe amenities, including oversized glass enclosed rain shower and plush bathrobes. All Cheeca Lodge accommodations offer complimentary Wi-Fi.

Cheeca Lodge & Spa
At Cheeca Lodge & Spa, the Lodge Oceanfront King Suite has a large open air balcony with views of the Atlantic Ocean. (Cheeca Lodge & Spa)

For those who want to head out for local shopping or dining, the lodge has a complimentary shuttle service for drop-off and pick-up within two miles. Or guests can instead opt for a pampering treatment at the 5,700-square-foot Spa at Cheeca Lodge. Tip: We’d suggest the 50-minute “Anti-Aging massage,” designed to help heal the body, hydrate and ward off premature aging with new probiotic rituals. 

That said, pool play, snorkeling, scuba diving or sea kayaking also await, along with the fastest growing sport in the U.S.—yes, it’s the wildly popular pickleball. Tennis fans should ask about the lodge’s tennis clinics hosted by a USTA professional. If guests like to fish, at the resort’s pier they can cast a line with saltwater fishing rods, reels and a fishing license provided by the resort. There’s also a game room and an Xbox arcade with an extensive game library. Nice for book lovers is the “take one, share one” collection. 

Good to know: The resort’s nine-hole executive golf course, currently closed for renovations, will reopen in December. 

The general manager here is Paul Scott, while the go-to person for travel advisors is Marje Jones ([email protected]; 305-517-4449), director of sales and marketing.

For those planning an event, large family reunion or sizable wedding, the lodge just opened its new, stand-alone, 10,000-square-foot Islamorada Ballroom, which holds up to 1,000 guests for receptions and 788 for banquet-style dinners. Retractable walls also create three break-out rooms for smaller events, weddings and functions. There’s also 12,000 square feet of outdoor space, and the ballroom’s terrace offers an expansive, pre-function area.

This resort also has an exclusive, gated-access Casitas neighborhood with 750-square-foot to 2,100-square-foot home-like rentals. One small home rental is perfectly sized for a solo traveler or a couple, while others are larger with multiple bedrooms. Guests staying here have access to a Casitas’ tennis court, pool and private beach. In some ways, it’s a home-away-from-home experience as each Casita is equipped with a full kitchen and washer-dryer. But you can also count on a butler for personalized service. We’d ask the lodge’s concierges, Rick or Mike ([email protected]) to set up either a private chef’s dinner in your Casita, or alternatively, a champagne dinner by water’s edge.

South to Marathon

On the southward drive, travelers will see many original bridges from Flagler’s railroad, built between 1905 and 1912. Today, they’re still massive, stark and interesting to view alongside the Overseas Highway’s more modern bridges. The Old Seven Mile Bridge was closed to the public in mid-2016 due to safety concerns, deterioration and weathering by time, storms, sunlight and salt spray. Fortunately, a two-mile section of the bridge leading to historic Pigeon Key was restored and opened for pedestrian recreation earlier this year.

We’re particularly excited about the new, 60-passenger Pigeon Key Express, an ADA-compliant blue-and-yellow tram that’s now transporting visitors across the Old Seven Mile Bridge to historic Pigeon Key, nestled beneath that historic bridge span. Consisting of a locomotive-style front that pulls two 30-passenger coaches, the tram departs from the Pigeon Key Visitor’s Center, MM47.5 bayside, just north of the Faro Blanco Resort & Yacht Club. Travelers can purchase tickets at the visitor center or at pigeonkey.net.

Once at Pigeon Key, visitors can explore on their own, take historical tours or explore a museum, which is expected to soon have ADA-accessible ramps. What’s special? Pigeon Key was once home to about 400 workers who helped build the Over-Sea Railroad; the isle also served as a supply depot, dormitory with commissary and passenger train stop during the early 1900s Flagler era.

Nothing beats the scenic experience, though, of driving over the modern-day Seven Mile Bridge, which connects Knight’s Key, part of the city of Marathon, FL to Little Duck Key in the Middle Keys. Another scenic experience is staying as a guest at the exclusive Little Palm Island Resort & Spa, reachable via a boat transfer from the property’s welcome shore station at MM28.5 or via seaplane to Little Torch Key; the isle has no cars. One interesting factoid is that the 1963 movie, “PT-109,” starring Cliff Robertson, was filmed at this idyllic spot.

Stepping off the pier onto the four-and-a-half-acre private island or arriving via a chartered seaplane, luxury travelers will discover an adults-only paradise with crushed seashell exterior pathways and thatched roof bungalows inspired by British West Indies design. We’d describe this idyllic resort with its own private marina as “luxury in its purest form. One unique feature? To help travelers disconnect from life’s distractions, there aren’t any televisions or phones in guestrooms. Although Wi-Fi is available, cell phones must be set to “silent.” 

Amid towering palm trees and with beach and ocean views, the island’s Great House is a guest gathering point. Head for its second-floor Great Room, a comfortable living room for reading, playing games or relaxing on decks; it also has the isle’s only television. Nearby is a large pool with a tropical setting, as well as a cool cocktail at the Palapa Bar.

For our Dining Room lunch, we savored Key West pink shrimp cocktail and an organic greens-and-grains salad. Note: The resort’s Caviar Menu includes an imported Royal Kaluga Huso, a natural hybrid of huge firm beads with a buttery profile.

The 550-square-foot “Island Romance Suite,” has a luxurious interior, separate living and sleeping areas and a bathroom with a deep soaking tub. Most enticing, though, is the suite’s large terraced deck with a copper outdoor tub and shower plus a couple’s lounger. That said, we also loved this suite’s small, exclusive sand beach with fire pit. 

Contact [email protected] to ask about a Great White Heron Wildlife Refuge eco-tour or a Looe Reef Scuba Diving Trip. Professional scuba instructors guide every dive. Tip: The shallow reef is pleasant for novice divers yet experienced divers like the eco-diversity.   

Heading to Key West

Driving the Overseas Highway south to Key West, our journey traversed Big Pine Key, home to about 800 endangered Key deer. Note: Watch for yellow roadway signs that warn drivers of Key deer crossing spots.

Stop in Big Pine Key at the new Pine Channel Nature Park, MM29, a scenic viewing area with a 9,500-square-foot boardwalk and 11-foot raised deck. Swimming is permitted, and travelers will also find restrooms and a kayak and canoe launch area. 

At Key West, the end of the Overseas Highway, travelers will discover a bustling city with a small-town feel, hefty cultural and heritage sites, and yes, a quirky vibe. One exclusive experience we highly recommend is the new “VIP White Glove Tour” at the Harry S. Truman Little White House. A solo traveler or up to six in a party can book this private, behind-the-scenes experience with added inclusions and access to rooms not on the normal home tour. Most notably, they’ll head out on the “ultimate ride around town” in a 1950 Lincoln Ambassador, one of President Truman’s luxury limousines.  

We spent two nights at The Marker Key West Harbor Resort, 200 William St., nestled on two acres of tropical landscape close to the Historic Seaport Area. Yunior Rodriguez serves as general manager. Think of it as part boutique hotel, part luxury resort. One location benefit is that guests can walk to an amazing array of eateries just steps away, plus the resort has an on-site restaurant and bar. 

The Marker Hotel
The Marker Hotel has 96 rooms and suites, three pools, and one onsite restaurant and bar. (The Marker Hotel )

For luxurious digs, book the Serenity Suite, No. 130, sporting a large living area (with pull-out sofa), dining area, separate bedroom with king-sized bed and spacious bathroom (including a clawfoot tub and separate rainforest shower). Plus, there’s another guest bathroom. The suite has a large private balcony with views of the adults-only Serenity Pool and Serenity Zen Garden. Guests can also swim at two other resort pools, work out in a fitness center and enjoy beach and spa access at sister property, Southernmost Beach Resort, 1319 Duval St. 

Advisors can reach out to Laurayne Croke ([email protected].; 305-295-6500), director of sales and marketing, for The Marker and the Southernmost Beach Resort. Helping guests plan fun activities on site is third-party Key West Concierge, which doles out sightseeing advice, books day tours and arranges customized private charters. The concierge operates from a desk near the front desk. Text 305-800-3879 to arrange everything from ski tours to parasailing, and even electric car and Jeep rentals. 

Nightly, we observed guests walking from The Marker to Mallory Square, famed for its sunset celebration, art stalls and amazing “acts” such as a juggling flame thrower. Parting advice? Enjoy the sunset, and then do as the locals do—head for Blue Heaven. The reward is casual dining outdoors under a canopy of towering trees, live music and fresh seafood, including barbecue shrimp and grouper.

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