Visiting the Florida Keys, particularly Key West, particularly Hemingway's Home, has been on my bucket list for ages. After nine years of stalling, we finally decided to make the trip with some friends over Memorial Day weekend. We were doing this! The decision was made. We booked a hotel on Key West. And then...murmurings of a less-than pleasant forecast for the weekend began to emerge. Tropical Storm. Possible Hurricane. High winds. 100% chance of precipitation. Probably blinding rain. Some likelihood of water spouts. Maybe tornados. 

But I had waited nine years for this trip and we were not backing down. We were driving to the Florida Keys, crossing that Seven Mile Bridge, and arriving at Hemingway's doorstep -- weather be damned!

8:00am

We meet up with our friends at the local coffee shop, grab drinks to go, fuel up our tanks, and are on the road by 8:30 with dreary skies and dark clouds looming. 

11:00am

We hit Key Largo and begin the long trek across the Keys. My whole life I've been waiting for this moment, when the trees clear, and you come up over the bridge, and those turquoise vistas stretch out in all directions. 

A "key" is a low-lying reef or island. To paint a picture of this, as we drive the roughly 100 miles from Key Largo to Key West, oftentimes the water is visible a stone's throw from the road on either side. Hemingway's Home, one of the highest points on Key West (second only to the cemetery), is a mere 16 feet above sea level. Can you imagine what it looks like when a hurricane hits? Driving along, I picture waves crashing over the land, submerging the road, mixing up all of the homes, cars, trees, in a sloshing whirlpool of debris. It's amazing how many structures seem to be intact after Irma, although the stripped mangroves, obliterated trailer park and tell-tale water marks give away the damage these islands endured. 

12:00pm

We stop at Islamorada, a village encompassing six of the Keys. Robbie's Marina is on the northern tip of Lower Matecumbe Key, and we discover it's an ideal pit stop if you're coming down from Naples/Miami and heading all the way to Key West (another hour and 45 minute drive). We enjoy a pleasant lunch at the Hungry Tarpon, situated right by the water. While the stormy weather keeps us huddling under the small amount of shelter offered -- most of the seating is out on the dock -- I imagine how beautiful it is to eat there on a sunny day. 

Lunch is over, so we walk next-door to Robbie's, where we buy admission to the marina's dock ($2/pp) and a bucket of bait ($3) to feed the live tarpon. This proves to be a highlight of our trip. Tarpon can get up to 7-8 feet long. They are silvery in color, and as they dart in and out from under the dock, their scales catch the light and sparkle, even in the rain. 

I don't do any of the fish-feeding myself, seeing as the dock has a number of people on it, and I have Frances in the Ergo on my back. I sort of clutch at the dock poles praying no one knocks us in. There are a few daring souls laying down on the dock dangling bait just above the surface. Tarpon leap out of the water and snatch the bait. It's exciting to watch as a bystander, but I am terrified someone is going to get bitten (turns out that's not entirely uncommon). 

The rain is coming down on and off, and the whole area is flooded (I guess the Keys don't have great drainage), otherwise we would've stayed to explore more. There seems to be lots of shops and kiosks and quaint derelict buildings, like this one: 

4:00pm

We arrive at our hotel in Key West by mid-afternoon, settle in, and sign up for the hotel's shuttle service back and forth from Mallory Square (everything we read beforehand suggests finding parking can be a real pain). By 4pm, we are boarding the newly-dubbed "party bus" and heading downtown.  

In spite of the gloomy weather, we set out to explore the city by foot. For the next several hours, we wander around Mallory Square, up and down Duval Street, check out the Basilica of Saint Mary Star of the Sea, walk by Hemingway's Home, go in and out of stores -- all in the pouring rain. At one point, we break down and purchase ponchos. Yes, we look ridiculous. Yes, we stick out. Yes, we have to rip them up to accommodate the babies in the carrier and in the stroller. But the silliness of it all keeps our spirits up.

7:30pm

Soaking wet, starving, and searching for a place to eat dinner, we happen upon Island Dogs. With the tagline "Come as you are," we take them at their word, and trudge through the doorway in our ponchos. 

We have every intention of catching the Sunset Celebration that happens each night on Mallory Square, complete with vendors, performers, and applause as the sun dips beneath the water's surface, but we find ourselves entirely drawn into the atmosphere of the bar. A live band plays reggae-style music, 11-month-old Frances bops along, and 2.5-year-old Catherine jumps and dances and twirls by the stage. (She even gets a shout out: "Catherine's in the house!") 

I have to be honest, I was a bit hesitant about our dinner prospects on a Saturday Night in Key West with two little kids. The island is beloved by spring-break college students, bachelorette parties and bro bashes for a reason. A lot of the spots on Duval Street are loud and crowded, some spilling out on to the street despite the rain, and the atmosphere wasn't, shall we say, quite family-friendly (the bar with a Garden of Eden loft, where clothing is optional, might give you an idea). 

We had to eat somewhere, we desperately wanted to sit down and dry off, so we ducked into the first place that seemed like it might work out for us. I remember, early on, looking at the t-shirt-covered wall across from our table, puzzling over who would buy logo-emblazoned paraphernalia from a bar. By the end of the night, I was wishing for one of those Island Dog tanks myself. 

The night closes out with ice cream, key lime pie, and cookies the size of your face at Mattheesson's. (I'm still dreaming of that soft peanut butter cookie "iced" with their house-made fudge. I see a test kitchen project in sight!)  

Sunday, 7:30am

No rest for the weary. Even though we fell asleep around midnight, the girls are up and at 'em early. Quietly we sneak around the hotel room getting ready without waking anyone else. We pop open the door, step outside and Catherine squeals, "Too bright!" It's a gloriously sunny Sunday. 

After breakfast and a swim, we pack up the car and head back to Mallory Square. In the dreary rain the day before, the Square was something of a dismal prospect, with a strange mix of stray roosters and cats skirting around. Today, the pavement is bright, the skies clear, the water blue, and those roosters don't appear just so random. They fit the quirky, cheery landscape. 

We hit up the Hemingway Home first thing. The tour is strange, yet informative. Our guide through the home seems to relish the more lurid aspects of Hemingway's life, and wonders openly when we fail to laugh. I myself feel torn throughout--fascinated by the the architecture and design of the home (built in the mid 1800s), interested in the history, obviously in awe of the writer's genius, but musing on the sadness of his life, and failing to see the humor of a man working through four wives, battling depression and eventually taking his own life. 

I stand in his study and feel, more than reverence, pity. Here was a man, really a "macho" man, tall, dashing, daring and a celebrity to boot -- by all earthly measures a man to be admired and adored -- but what a tragic mess.

Conflicted, I descend the steps from his garage study, overhearing another tour guide inform a group that the base of the fountain at their feet is really a urinal Hemingway pulled from a renovation of the famous Sloppy Joe's on Duval Street, where he could reliably be found drinking any day after noon. That's bizarre. 

The mixture of high and low throughout Key West is certainly a puzzle. 

1:00pm

We continue exploring the city on foot, grabbing tropical mixed drinks to go at a sidewalk bar. Standing in line for my Pina Colada, with a weed shop to the left, I joke how this is the college experience I never had (I was pretty studious in college). Walking down the sidewalk in Key West, sipping a drink with a baby on my back. 

After a delightful lunch at the Banana Cafe (a real Key West experience -- there wasn't even air conditioning where we sat!) we walk down to the Southernmost Point Buoy. There's a long string of people stretching down the sidewalk waiting for their turn to take a photo with the buoy.  Looking out at the ocean, with Cuba roughly 90 miles south, we spot land jutting out to the right that looks a lot more southern than we are. Turns out, this land is property of the U.S. Navy and not publicly accessible. Hence, no tourist buoy. There's actually yet another point in the Florida Keys that is more southern, Ballast Key, but that's a privately held island and not open to the public. 

Well, we do our obligatory homage to the Southernmost Point Buoy anyways, even if it's a fake. 

Slowly, with tired feet, we make our way back to the downtown area. In our wanderings, we happen upon Margaritaville, which proves to be a shock: clean, sterile, manicured, impossibly nice. It's like walking onto the set of the Truman Show. This is where the cruise ships dock (no surprise there!). It reminds us of our home in the Napless area.

When we first arrived in the Keys, coming from Naples, everything appeared so...dingy. In Naples, everything is just so. We have miles and miles and miles of beautiful white sand, meticulously maintained and kept clean. The wilderness of Florida is constantly kept at bay. 

Don't get me wrong--I love living in the Naples area. But, stumbling into Margartiville, where everything familiar was made foreign by our brief stay away,  I realize just how much I have come to enjoy the quirky character of the Keys, with its "hear comes everybody!" attitude. 

5:00pm

We kiss Key West good-bye and hit the road for home. We had originally planned to stop at the Florida Keys Brewing Company in Islamorada on our journey back, but since we were making good timing we decide to press onwards, stopping for dinner just after we cross from Key Largo to the mainland, closing out our 36-hours on the Florida Keys. 

if we had another 36 hours...

We definitely would go back! In a heartbeat! Here's what we'd do: 

• Spend more time in/on the water. Because of the weather, we didn't plan on it our first trip. I'd also have to do more research on what you can do with children, but the Keys are really famous for the boating, fishing and snorkeling opportunities. (Not really for their beaches; Key West is a deep sea port and so all the beaches are man-made.)

• Plan a trip to the Dry Tortugas, a national park accessible only by water, complete with camping, snorkeling, and a 19th century fort used as a prison during the Civil War.

• Visit the Truman Little White House, which was originally constructed as naval officers housing in the late 1800s, and which served as Truman's Winter White House during his presidency.

• Take a boat out to the deserted Pigeon Key and tour the abandoned buildings. (Driving past on the Seven Mile Bridge, it reminded me of the DHARMA compound from Lost!)

• Eat at Azur or Bagatelle (both options had good reviews and I had hoped to squeeze them in on this trip).

• Stop at the Florida Keys Brewing Company.

• Get another peanut butter-fudge cookie from Mattheesson's.