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Having just come out of a blast of winter weather featuring snow, freezing rain and bitterly cold temperatures, I’ve been craving some warm, tropical weather. Combine that with my Facebook memories showing me posts from January of 2022 when we traveled through the Florida Keys, and I’m having quite the time not cashing in all my Alaska Airlines miles to jetset to the Conch Republic.

Changes in Latitudes

We had spent the previous day in Big Cypress National Preserve and Everglades National Park, and were eager to get down into the Keys. The only other time I had been to them was during high school on a weeklong “high adventure” trip through Boy Scouts of America, which operates a sailing base in the Middle Keys. Under sunny skies with a mild breeze, we headed south on U.S. 1, known in these parts as the Overseas Highway, pulling off a short while later at Island Home Garden Center in Tavernier, where I had heard about a local secret called Gardenia’s Bistro, known for fresh breakfasts including empanadas, avocado toast and fruit bowls plus tropical smoothies, iced teas and mimosas, all in a lush garden setting with free roaming cats and chickens. Sadly, we happened along during a brief closure for maintenance, and had to settle for simply wandering the grounds, which are inviting and relaxing, despite being mere steps from the highway. Towering palms, orchids in bloom, and all sorts of hanging plants and unique finds from tropical locales around the globe create a slow-paced vibe and charm, urging you to stay awhile.

After this welcome slowdown to truly introduce us to island life, we lucked out and found a short line at Midway Cafe & Coffee Bar a few minutes farther along in Islamorada. Breakfasts are simple but satiating here…you can’t go wrong with Everyone’s Favorite Sandwich, a cinnamon roll and a poppyseed muffin, paired with an iced coffee. Kick back in the eclectic outdoor seating, where you’re likely to encounter more locals than tourists. As Kjirsti sunbathed in a well-worn adirondack chair, we conversed with a longtime local who escaped Cuba during his teen years. Donning a light cyan Columbia PFG performance long sleeve, running shorts and a white bucket hat, he regaled us with the histories and changes of the neighborhood, and let us in on some of his closely guarded secret places to stop.

Poets & Pirates

We each had picked up new books a few days prior on Sanibel Island, and were eager to get back into them, so I hit the brakes and made a hard turn back into Long Key State Park, which was the historical home of railroad magnate Henry Flagler’s fishing retreat for the well-to-do in the early 1900s before being razed by a 1935 hurricane. We first strolled the hiking loop through endless stands of dying mangrove, so severely damaged by 2017’s Hurricane Irma that they have been reduced to lifeless sticks, a stark reminder of the catastrophic impact weather can have on critical native ecosystems. Mangroves live in coastal intertidal zones, and are highly adapted to periodic submersion in brackish water. Their root systems provide critical habitat for fish and juveniles of other marine species, while the greater network of their forests provide essential buffers from storm surge and coastal flooding for local communities. They are also one of the most efficient storage systems of carbon, but are regularly under threat worldwide from development, pollution, weather damage and changes in the local environment.

We ventured to the beach, where we found a raised platform right above tide level, featuring a vine-covered trellis and pool loungers under the dancing fronds of a palm tree. As I dove back into David Cordingly’s Pirate Hunter of the Caribbean and Kjirsti rejoined the P.D. James mystery recommended at the bookshop, thunder rumbled in the distance as storms wandered the open ocean to the east (for those interested in pirate lore, Republic of Pirates by Colin Woodward is a great place to start).

Nothing to do With Accords or Civics

With a couple chapters paged to the left, we marveled as we crossed the Seven Mile Bridge, making our next stop at Bahia Honda State Park, one of my favorite stops on my teenage sailing journey. On that trip, we moored in the tiny harbor on the western tip of the key, and camped on dry land instead of sleeping on the open deck. This time around, we strolled first up the Old Bahia Honda Bridge, which extends a few hundred feet out over the sea, with an altitude that provides a bird’s eye view of the island below. With a sharp breeze off the passing storms, I ratcheted down the tightness on my ball cap by one more node; as we paused for a selfie, a young father behind us experienced the full force of the wind, as his umbrella went tumbling away and he lunged after it, all while trying to maintain a grip on a stroller. We returned to sea level and the expansive Calusa & Loggerhead Beach to wade in the bathtub-like aquamarine water.

With midday passing, we brushed the sand off our feet and made the long jump over the remainder of the highway to Key West. Along the way, we passed periodic access points to the Florida Keys Overseas Heritage Trail, with over 90 miles in segments completed of the planned 106-mile span from Key Largo to Key West. According to the Florida State Parks site, “Paralleling U.S. Highway 1…[it] incorporates 23 of the historic Flagler Railroad bridges, offering a scenic venue for hiking, running, bicycling, skating, sightseeing, fishing and paddling.”

The Edge of the World

Key West is a lively and robust town, all at once a haven for tourists and beach bums, artists and outdoorsmen, families and partiers. Much in the spirit of Bourbon Street in New Orleans or Broadway in Nashville, Key West dresses in a whole new attire as night falls and the revelers come out. For those into the true island “anything goes” vibe, Duval Street provides the perfect nightly haunt; for families or those less inclined to the party scene, Key West offers a slate of fun and unique opportunities and locations (In case anyone is asking, we fall into the latter category).

After checking in to L’Habitation Guest House, a circa 1874 B&B half a block off Duval, the 75 degree afternoon was inviting us outside, so we walked to Fort Zachary Taylor to peruse the remainder of a pre-Civil War bastion that currently houses the largest collection of Civil War armament in the country. The tunnels and corridors take on a vibrant life as the sun gets lower in the sky, with golden beams dancing through the windows and doorways. As a classically-trained singer, Kjirsti appreciated the acoustics of the arching brick ceilings; at the far end of the battery, a photographer staged a sharply dressed couple in an engagement photoshoot. Along the walk to the fort, military and political history lovers can tour the Truman Little White House or the Coast Guard cutter Ingham. Other local favorites include the Mel Fisher Maritime Museum and the Key West Shipwreck Museum.

Audacious Audubon and The Importance of Being Ernest

For lovers of the arts and nature, Key West boasts a trio of wonder. The Audubon House & Tropical Gardens features an 1840 home of Captain John Huling Geiger, and now houses a collection of the works of John James Audubon. A few blocks southeast, The Hemingway Home and Museum is open for tours of the estate where Ernest Hemingway penned so many great lines, though perhaps the most intriguing part of the visit is the colony of 60 polydactyl (6-toed) cats, all descendants of Snow White, a 6-toed cat Hemingway received from a ship’s captain. Closer to the ocean, the Key West Butterfly and Nature Conservatory features a glass-domed structure full of free-flying butterflies and exotic birds.

The walk for this itinerary will also take you past the Key West Lighthouse, open for visitors to climb the 88 steps to the top of the tower. After hours, small groups can enjoy the grounds to themselves at the Lighthouse Sunset Experience, along with shareable prosecco and a meats and cheese assortment. At the end of your walk, hop one block west to the Southernmost Point of the Continental US, one of the most Instagrammed spots in the Keys. There will likely be a line to get a photo, but most everyone is willing to extend the courtesy to snap a couple shots for the group in line ahead of them (don’t be that guy who breaks the trend).

Island Fare

After an afternoon of adventuring, Key West showcases a menu with dozens of local spots to eat, from small cafes and seafood joints to high end bistros, along with several options for great craft beer and rum. My favorite was Moondog Cafe, with a cozy string-lit deck and a kaleidoscope of art and decor inside. Start with a basket of Truffle French Fries or Cast Iron Truffle Mac n Cheese, before digging in to Blackened Local Mahi Tacos or The Frenchman Burger with onions, brie, arugula and honey-garlic jam. Festive cocktails and local craft beers round out the menu. Stop back in the morning for Quiche Lorraine or a Blackened Shrimp Benedict with a Mango Mint Mimosa and a Classic Butter Croissant. 

Another great family spot is The Waterfront Brewery along the historic Key West Bight, where we shared a platter of Baja Pork Nachos, beers off the rotating in-house tap list and a slice of Key Lime Pie. Pre-dinner, stop in to Key West First Legal Rum Distillery for a tour and a tasting flight of the multiple rum options available.

Late in the evening, we took a quick (and eye-opening) shortcut along Duval Street to get back to our quarters for the night. Though not really my speed, the cultural experience doesn’t quite fit any mold, and perhaps parallel universe me would have really taken to it. I do have to say the biggest highlight of the walk was a random dude hiding behind a fake ficus tree who would jump out and scare people as they walked by. I was mildly startled, but Kjirsti really let out a shriek; we laughed down our adrenaline as he slinked back into the shadows, only to hear another round of squeals ring out as he caught a passing group of sorority girls some 30 seconds later.

We had a quiet night in our spacious room, followed by a simple breakfast on the front porch as the sun rose and (some of) the town shook off their slumber. Since this was still during Covid, breakfast was limited to individually wrapped items, but still featured egg and pastry options, fruit and accompaniments such as yogurt and juice. Just 3 addresses to the east, we followed up with a stop by Glazed Donuts, home to numerous incredible donut options including Guava Jelly, Meyer Lemon Pistachio and Maple Bourbon with Candied Bacon, along with house roasted coffee and (proudly) paintings of giant robots. Leaving the robots on the walls, we took our coffee and donuts back to the porch and were the sudden envy of the other guests who had begun to venture outside. After a quick stop at the Mile 0 marker for an obligatory selfie, we were on the road and headed north. 

We made a handful of stops on our morning drive, including time to step in the water at Anne’s Beach, which was nearly deserted, save for a few morning sun bathers with their camp chairs parked in the shallows. The day was sunny and pleasant, with billowing thunder cells skulking about over the open water.

Milestone Breweries

Around lunchtime, we eagerly parked at Florida Keys Brewing Company to commemorate a special milestone: our 300th brewery visited in our travels across (at the time) 46 states! We celebrated with a couple pints off the seasonal menu, and some astounding street tacos from Tacos Jalisco food truck. We savored our meal as the resident cat slept nearby in a shallow cardboard box, a feline take on living on island time.

Grabbing a 6-pack of Iguana Bait Kolsch to go, our next hop stop was just steps away, continuing the celebration at Islamorada Brewery & Distillery, which, at #301, is still one of my favorite craft beverage stops in our travels. Whether imbibing on site or taking beer to go, you can’t go wrong with the No Wake Zone Coconut Key Lime Ale. On the distillery side, the Select Single Barrel Rum is one of the best we’ve tried…smooth, slightly woody, with just a hint of sweetness.

With a bag full of beer, rum and merch (including my favorite performance long sleeve that is a must-pack any time we’re heading out to the beach) we got back in the rental car and drove off, agreeing with the sentiment of Jimmy Buffett about “changes in latitudes, changes in attitudes.” 

All photos and content © Eric S. Allan 2022-2024

For media and publication inquiries: eric@corneroffirstandadventure.com