A Keys Road Trip

The Keys Are Now Open Again, and What Better Place for a Summer Escape

Sponsored by Mercedes-Benz of Coral Gables

The water was crystal clear over the white sand, with green islands in the distance. Leading south from the beach was a trail through a forest of gumbo limbo and mangroves. On a deck overlooking the beach they were serving daiquiris and mojitos.

This is what the Caribbean is all about, I thought. Except that it wasn’t Antigua or Aruba. It was Key Largo.

With the Keys now open again, and a general consensus that driving is far safer than flying these days, the necklace of islands that stretch from Florida City to Key West is more alluring than ever. Open since June 1, we decided to head south to Mile Marker Zero, and to take our time with a few stops along the way, in two teams of travelers. Here’s what we found.

Team One: Key Largo

Our first destination was Baker’s Cay Resort. This eco-friendly enclave was named for Ben Baker, who started a pineapple plantation in Key Largo in the late 1800s. Originally carved out of a natural hammock in 1985, the resort was rebuilt after Hurricane Irma, and reopened as a Hilton Curio property in February last year. It prides itself on its natural setting, with a biologist caretaking what is now a protected tropical hammock. It also brought in literally tons of white sand to create a pristine beach with translucent waters.

Entering the gated compound was our first experience of the COVID changes: A mask-wearing guard at the gatehouse checked us in and pointed us toward our room. No bell boy at a front desk here. Another new sign: Our room had a paper seal across the door under the handle, certifying that no one had entered since it was last sterilized.

Like many of the hidden gems of Key Largo, Baker’s belies the clutter of touristy shops that line U.S.1. Interspersed with stunning views of aquamarine waters are clusters of fast food outlets, gift shops, tattoo parlors, psychic readers, scuba rentals, and key lime pie vendors. But off the beaten path you will find places like Skipper’s Dockside, a restaurant on a working canal at Mile Marker 100, with a big open area behind what used to be an old icehouse and a 1940s filling station. We decided to eat dinner here because of their smoked fish dip, shrimp ceviche, Bahamian red conch chowder and mango coleslaw. Like restaurants in the Gables, it was masks on the way in and socially distanced tables inside. But unlike the Gables, it was on a waterfront canal with dive boats and lights that shimmered as dusk settled in.

We couldn’t leave Baker’s without dipping into the cool waters of their beach; a fair number of families were playing there, taking out kayaks and paddle boards. We also couldn’t leave without breakfasting in the Calusa restaurant. On the third floor of the main building, it overlooks the hammocks and out to the Florida Bay. The sensation was like being on a hillside in Jamaica. After French toast, bacon and coffee we took a last lie down on lounge chairs discretely placed in the hammock at water’s edge. Then it was back on the road.

Team Two: Islamorada

The next major key after Key Largo is Islamorada, a narrow strip of land where just about everything is right off Overseas Highway – like Cheeca Lodge & Spa where we spent the night. Located on 27 acres with 1,200 feet of Atlantic beachfront, it’s a world of its own. With daily snorkel excursions, jet ski tours and sunset cruises, there’s plenty to do even if you don’t leave the property – including a nine-hole par-three golf course. Or you can dismiss the notion of physical activity and lay on the beach or by one of the resort’s two pools, a blackberry margarita in hand. 

Cheeca Lodge is also in the heart of Islamorada, close to Village Square behind The Trading Post grocery store. This hidden shopping center looks more like a village for elves than for full-grown people, but that’s part of its charm. Behind the overgrown entryway, there are miniature shops, a cafe, even a small taco stand in a back corner. And when we say that it’s right across the street, we mean it – just don’t get hit jaywalking across Overseas Highway. 

A quarter mile south from Cheeca is Morada Bay, a casual beach café that boasts the perfect setting for lunch or a sunset drink. For something more upscale, go next door to Pierre’s. For dinner, Marker 88 is an Islamorada tradition. Located on one of the few natural beaches in the Florida Keys, it’s among the best places to dine and watch the sun slip behind the horizon. We ordered a key lime pie martini – made with Citron vodka, Ke Ke Beach key lime cream liqueur, pineapple juice, and fresh lime juice, with a graham cracker rim. Only the sunset was prettier.

Back at Cheeca, we took an evening stroll on its 525-foot wooden pier. At night there are a million stars overhead; during the day it’s perfect for fishing. Islamorada is known for its world-class fishing, so don’t be surprised if your elevator companion is a boy with a fishing pole twice his size. The suites are also luxurious, complete with a sitting area, expansive bathroom, and balcony with a table, chairs and Jacuzzi. If you get an oceanfront suite, you can sip your morning coffee on the balcony with views of nothing but blue. Cheeca also offers several dining options. Our recommendation: Atlantic’s Edge, literally right on the ocean, with indoor and outdoor seating open for all three meals. The outdoor patio runs into the beach, and there isn’t a bad seat in the house.

Hello, Old Chum 

Robbie’s Roadside Attraction

Driving south from Islamorada, don’t forget to stop at Robbie’s, a tourism mainstay where you can grab a bite to eat, shop for trinkets or feed giant tarpons. That’s right, feed giant tarpons.

From a distance, with their fins sticking out of the water, the tarpons who circle the docks at Robbie’s look like small sharks. But after paying a few dollars to get closer with a bucket of fish, you realize it’s a swarm of hungry tarpons who know that Robbie’s is the place to eat.

You can either toss the bait from the bucket into the water and watch the feeding frenzy or hold it just above the surface and wait for one to jump up and grab it out of your hand. After hand-feeding dead fish to bigger fish, we have never been so grateful that hand sanitizer is now commonplace. 

Their website, by the way, has a live webcam so that you can see what is happening on the docks at any time, just in case you want to check the action.

Team One: Marathon

The final big island and town on the way to Key West is Marathon. It has the same U.S.1 lineup of fast food and tourist shops, along with waterfront eateries, beach clubs and a municipal airport. It is also home to the Florida Keys Aquarium Encounters attraction and Crane Pointe Hammock, a preserve you can tour. We were too close to Key West to stop for another night, let alone a family attraction, but we did stop to eat at Isla Bella, Marathon’s newest and most posh beach resort.

You need to make a reservation to get past the gate, but once inside the compound you proceed to their Il Postino restaurant. It is inside a Dutch West Indies-style building, with a large, beachfront veranda surrounded by coconut palms. The experience of breezes and light on all sides, on a point of land that overlooks the Seven Mile Bridge, is sublime. The food, says Chef Josean Rosado, “is Italian inspired, using as much of the local produce as possible. You don’t have mahi mahi, in Italy.” But you do at Il Postino, where it’s served blackened on a bean and black olive puree, with spinach and sautéed red peppers and purple onions. 

Team One: Key West

There are two immediate impressions you get when you come to Key West in the post-COVID era. First, it is a lot less crowded than usual. Second, few people seem to care about wearing masks or socially distancing, at least in places like Duval Street, the main commercial drag. Almost no one wore a mask in the shoulder-to-shoulder line of people waiting to take selfies at the Southernmost Point, for example. “I just won’t live in fear,” tourist Emily Ardis told us. Visiting from Pensacola, Ardis said her aunt lives in Coral Gables, where she is “quarantined with her husband. I want her to read that I am traveling, because she gave me so much [grief] about coming here.”

Many others we talked to had similar attitudes. One couple from Texas told us that “people who come to Key West aren’t the type who wear masks.” On the other hand, a woman from Miami told us, “This is crazy. Look at these people without masks!”

The good news is that Key West is a place where most restaurants are either outdoors or completely open and breezy, and where there is plenty of room to socially distance if that is your choice. Monroe County regulations require masks to enter any retail establishment. You can de-mask in restaurants and bars, of course, and there is the rub: some bars on Duval Street, for instance, are crowded with mask-free people. On the other hand, there are plenty of establishments that are highly cognizant of protocol.

At the Half Shelf Raw Bar, for example, a waitress takes your temperature before letting you inside. At Two Friends Patio Restaurant on Front Street, you can listen to live music while sitting at every other table. Masks are required at all tourist destinations, like the Hemingway House or the Mel Fisher Maritime Museum. Every person riding the Conch Train – on every other seat – had to mask up.

Even on Mallory Square, where the (thankfully) thinner crowds are back to see the sunset, the seawall where people sit is marked with red X’s six feet apart. We sat there and watched a blazing sun go down on our first evening. Behind us a local musician strummed a guitar while singing, sans mask, the 1960s dystopic ballad, “On the Eve of Destruction.” His attitude seemed typical. “It’s not like I’m shaking hands or kissing people,” he told us. “I’m just not wearing a mask unless I’m going into a store.” 

We stayed in two hotels in Key West, to get a take on the two sides of the island. Our first was the Barbary Beach House on South Roosevelt Boulevard, the long oceanfront road that runs along the south side of the island. This is a very different experience than staying in the Old Town. Here the entertainment is waterfront sports and swimming at Smathers Beach, bicycle riding, public tennis courts, walking out on long piers, or visiting a couple of old Civil War era forts that are now open again.

Barbary Beach House itself is a family-friendly compound across Roosevelt from the beach. Its rooms form a large square, inside of which is a garden walkway, pool, terrace restaurant and bar. Despite the family vibe, the food here is gourmet, the kind of place that freshly squeezes your morning orange juice; we would return just for their Thai lettuce wrap or their grilled vegetable gazpacho, both amazingly tasty. Their bar also has several signature cocktails concocted by staff during the lockdown. 

“We were just keeping ourselves busy,” food and beverage manager Batu Pektas told us. “We started to make our own ginger lime syrup.” From there they came up with combinations like their Rooster Margarita and Shipwrecker’s Gimlet. The margarita had a nice jalapeño kick, with cayenne pepper sprinkled on top. The Shipwrecker’s used their ginger lime syrup with pieces of cucumber, cucumber vodka and soda water. Delicious and refreshing.

The other hotel we sampled was The Marker, a relatively new, upscale hotel nestled in among the old seafront bars and eateries on Caroline Street. It could not be more different than funky Bo’s Fish Wagon down the block, or the Schooner Wharf Bar next to the hotel, where live music plays at night under a massive thatched Tiki hut. The Marker is a long, narrow hotel with noticeably fine linens, a serenity pool at one end, and bathrooms with that rarity in today’s hotels: a bathtub. The Marker has another two pools and bar out back; open to non-guests, this creates a lively singles’ and couples’ scene. We sat at the bar as a DJ spun tunes, watching the dance of hormones as the bartender poured a complimentary vodka drink (for guests) to get the juices flowing.

The Marker’s location could not be better, right along the pedestrian waterfront walkway that meanders past a plethora of waterfront restaurants, like The Conch Republic Seafood Company, Alonzo’s Oyster Bar and the venerable A&B Lobster House. We ate dinner at the Waterfront Brewery not half a block away, which has an exceptional selection of locally brewed beers on tap. We tried the Lazy Way IPA and the red ale Wrecked Rooster, both of which helped wash down an incredibly fresh filet of yellowtail as the sun set over the boats docked outside.

To the Keys in Comfort

Road Testing a Mercedes GLS 450 Down the Overseas Highway

Driving south from Islamorada, don’t forget to stop at I began this trip not a Mercedes fan. But after spending four days travelling 350 miles to and from Key West, I am now a major convert. 

The GLS 450, which the good folks at Mercedes-Benz of Coral Gables lent us for a road test, is a perfect combination of comfort, luxury, technology and power. This is a hard combo to come by in a car these days, especially in an SUV with three-rows of comfortable leather seats. As far as the ride itself, the smoothness was exceptional – especially on the highways going down to Florida City – whether you wanted to push the pedal or drive like grandma. It has multiple riding styles – comfort, sport, eco and custom – but we chose comfort, to minimize the experience of bumps in the Keys. 

Like most Mercedes, the GLS 450 was loaded with technology, and the interface could not have been easier: a touchpad on the center console, with a padded leather rest for your wrist while your fingers control everything from the dashboard appearance to options for music and sound.

I was also deeply impressed with the car’s cameras, which gave us options: the reverse view, the view from above, and a view around the corner as we backed up. The car made it virtually impossible to have a blind spot. Great for parking in tight Key West spots – and great for making long distance drives in safety. 
For information visit: www.mbcoralgables.com

Team Two: Key West

One big reason to visit Key West is to spend time in the Old Town – the western historic district that includes Mallory Square, Duval Street, the Key West Cemetery and Fort Zachary Taylor. Here the 19th century, wood-frame Bahamian style buildings, with their tin roofs, covered front porches and picket fences, are protected by local ordinance. Once you leave the commercial areas, walking through the old streets is a journey back in time.

Fortunately, you’ll find plenty of small boutique hotels in historic buildings that blend into the island’s quaint landscape. We chose the Marquesa Hotel, one of Key West’s prettiest historic getaways. From the front, the Marquesa looks like a large house, but inside you’ll find a handsome courtyard with two swimming pools, lounge chairs, patios of ground floor rooms tucked away on the side, and stairways that lead to second and third floor rooms. 

The hotel recently finished an expansion project half a block away – the Marquesa 4-1-4 – a compound of three vintage buildings with a swimming pool in the middle. Guests of the 4-1-4 also have access to two pools at the original Marquesa. And of course, all guests can dine at the upscale Café Marquesa, which specializes in contemporary American cuisine like local seafood and grilled meats, with a lengthy wine list.

Just blocks from Duval Street, the Marquesa is an oasis in the middle of the historic district. It is equally distant from the bluster of Mallory Square and the quietude of the Key West Cemetery (where we found the famous “I told you I was sick” headstone). It is also walking distance from the Historic Seaport if you want to take a sunset cruise. We set sail on the Appledore Star, which prides itself as the last Chesapeake Bugeye schooner ever built. This is significant because the Bugeyes were shallow draft two-masters suitable for the waters around Key West. From our socially distanced perch, the views were breathtaking, enhanced by the onboard drinks. 

Not within walking distance of the Marquesa (but worth the short drive) is Barefoot Billy’s. Located inside the Casa Marina Resort (Henry Flagler’s historic hotel), Barefoot Billy’s does boat charters, snorkel trips, kayaks, paddleboard rentals, and our choice: a two-hour guided jet ski tour. It’s not cheap – $140 for a single rider and $160 for a double rider – but it’s a real blast.

The guide took our group entirely around Key West, pointing out landmarks and recounting its history. Once you get to the Gulf of Mexico, you’re given 20 minutes of free time to zoom around the crystal-clear waters on your Yamaha Waverunner. On the way back, the group traveled through Cow Key, named for its manatee population. The guide called this the “lazy river” portion of the tour, as the channel is a no-wake zone for the sake of the water’s inhabitants. Sadly, no sea cows were spotted.

All of this was great fun, but at the end of our day of drinking and sailing and jet skiing, laying poolside at the peaceful Marquesa was the perfect antidote.

Overall, we found Key West to be almost back to its old self, with both pros and cons. Not everything was ready for prime time – Sloppy Joe’s was still boarded up and the old Mallory Square aquarium will not be coming back – but most places were open, and far less crowded than usual. And, for the time being, some hotels are offering bargain pricing to lure back the tourists. The downside is that, just like the rest of the world, the lurking virus means that you must wear masks inside and should maintain social distancing outside. But of all the places you might now visit, few are as bright and breezy and generally safe feeling as Key West and its sister islands.

Also read: Dog Days at Ocean’s Edge