Road Trip Blog

Best Laid Plans

Best Laid Plans

Enroute to Key West, my February excursion. Not an exotic or foreign locale, but a familiar destination where friends and the best kind of fun awaits. I could not refuse a friend’s generous offer to stay with her for a few days, after all, hot sultry breezes and blue water horizons are a life-sustaining balm to the pale-skinned Midwesterner at the end of February. Just the idea of stripping off my layers of clothes and laying this body in a halo of sunlight makes me swoon. I’m salivating thinking of fresh fish and cold margaritas and looking down to watch my pink painted toes wriggle in the sand.

My first two nights are booked at an Airbnb. I’m on a mission to find unusual places to lay my head at night and the Airbnb platform offers some interesting choices. I wasn’t having much luck in my search. Guest houses and condos in Key West are exorbitant and most of them are small and dark. When I stumbled upon the sailboat option I was intrigued. An increasingly popular overnight, they offer a way to spend a few days in Paradise for a total cost that won’t kill your bank account. As I read the reviews, I noticed a pattern. Five great reviews followed one scathing rant. Most people loved the solitude of being moored out in the harbor, having the option to snorkel off the boat, laying out on the deck, living the ‘salt life’ as the owners of these vessels opined. A laid-back attitude was mandatory, the owner insisted. Too many customers come out expecting a four-star hotel and all the amenities! He had a long list of finger pointing advice. This is Key West for Chrissakes! Don’t expect luxury. Okay. I was game. I’m not one of those ignorant fools who expects all the comforts of a world class hotel in a 26 ft sloop. I’d been on boats. I know the head is tiny and temperamental. See, I even know it’s called a head.  I know things break down. I pride myself on my ability to adapt. The photos looked adequate, cozy and clean. It would be an adventure!! Besides, the guy’s diatribe in response to those few inappropriate customer comments who hated the experience had me convinced that he was right to call them out for their uppity foolishness.

I hesitated though before I clicked the little red Book button. I would be staying out there solo. Sure, the owners offered a single ride out and back each day to where the boat was moored and if I needed to water taxis were available, but how safe was it really? I began to picture myself laying in the dark, surrounded by the inky blackness, listening to the romantic sound of waves slapping against the fiberglass, and then what was that? Voices…coming closer. And I’m alone. Are they climbing on the boat? Will anyone hear me scream? Yeah, so my imagination conjured up worst-case scenarios and I thought well maybe I’ll just a book one of those gloomy condos. Then I thought to email the owner, a guy named Chance and tell him my reservations. He answered in minutes. “C’mon down!” he boomed. (well, that’s how I imagined he spoke with gusto and assurance) He claimed he had many solo female overnighters and all would be well. He said I would be well taken care of. I imagined a nice grandfatherly type, an old salt, a Key West local, someone trustworthy and kindly. I was in.

Flash forward. I’m sitting in the GR Airport, giddy to be escaping the low ceiling of heavy clouds blanketing the area for the last few days. I realize with a start that I hadn’t heard from Chance, usually your Airbnb host contacts you a day or two prior to arrival with details. Oh well, he’s so chill and laid-back he is probably waiting to hear from me. I decide to check the reviews on a whim, just to see if anyone had posted more recent descriptions of their stay. Mistake. ‘DO NOT STAY ON THIS BOAT.’ Ok, seriously? Capital letters, is that necessary? I proceed to read the review and the guy, Greg, is vicious. Unusual for Airbnb reviews. The shower didn’t work and no one came to fix it. (ok, terrible but I could live with that. I mean, ya got a big bathtub right outside). Lots of things were broken. (okayyy.) Greg was stuck on the boat for hours and hours, Chance was MIA and he was stranded. Ruined vacation. (not good, feeding into my initial fears. Where were the emergency water taxis??) Finally, something about getting charged $220 for something. I’d stopped reading at this point due to my rising anxiety and my old Pollyanna habit of making bad things seem inconsequential. I figured that guy was just a crank pot. Old grandfatherly Chance got another bad egg. I glanced back down at the phone and saw that Chance had indeed responded. He sounded defeated. Disgusted. He said, “I’ve had enough. It’s cuz of people like you (said crank pot) that I’m not gonna do this anymore. I’m done.” Within minutes, the listing was inactive and I was left hitting my phone with my pointer finger over and over, hoping the listing would magically activate. The review disappeared along with it. Hmmmm.

Ok, I am going to pretend I never saw any of that. I email Chance, telling myself that I am the foolish one now. I’m wondering where am I going to stay? There goes the great salt life adventure.

But wait. There he is. Surprisingly prompt. “Hey Michele, let me know when you hit Key West and how you are feeling and we can go from there” Alrighty, then. Appropriately laid-back. He’s still expecting me, that’s good. Here we go then. I’m not sure what I’m heading in to but I’m going in with the intention of accepting whatever comes my way. Hey, if I’m stranded out there, I can think of worse places to be. Right?