I am not an obsessive worrier, and one glance at my mopboards confirms I’m no compulsive cleaner. Yet my approach to planning and scheduling screams OCD. I write a detailed to-do list every morning and every night. I compile lists of lists. I jot down completed items I forgot to originally note, just so I can literally cross them off. And, before I head out on a vacation, I plot every minute.
Clearly, I would never consider getting up one day and driving an hour to the airport, booking the next available flight out to wherever it was going, and then hopping aboard—with no hotel reservations, no car rental, and no itinerary. Until the day I did.
I wouldn’t allow myself to plan specifics of this new life experience, yet a few details did require forethought. I needed to hire a pet-sitter, schedule a couple days off work, and pack. But how does one pack for a weekend trip to a totally unknown location, especially in mid-March with its infamous lamb-and-lion split-personality? Considering I could land anywhere from Miami, to Denver, to Fargo, North Dakota, I made a packing list (thank God, this one list was allowed), covering all my bases with a bathing suit, cover-up, and a pair of Sperry boat shoes—but also a winter coat, gloves, and boots.
I also had to ponder how exactly I might pay for the trip. I had no idea how much this last-minute flight might set me back. When I posted my plans on Facebook the night before, readers began quoting me disturbing estimates. In a panic, I threw out a half-joking request for donated air miles. An hour later, a long-time friend offered me enough unused points for my entire flight. Score!
I called Delta and was assured I could simultaneously transfer the miles and book a flight at the Detroit Metro counter the next day.
For the first time ever, I was able to take my time that morning heading to the airport. Forget my usual race through the terminal, praying I didn’t miss my flight. This time, I knew I’d be right on time for some flight—I just didn’t know which one.
I wandered into the terminal, both excited and nervous about the possibilities of my weekend. I could wind up somewhere like Hopeulikit, Georgia or maybe Hooker Corner, Indiana (which I recently discovered are totally real towns). I was sure both these places were lovely. Still, I hoped I’d end up in a big city I’d never visited or even better, a warm beach somewhere, especially after the sadistic Ohio winter that kept roaring in my frostbitten face.
I approached the Delta counter and explained my long story to the attendant. She gave me a somewhat confused smile and said she’d love to help me. However, she had no way at all of knowing which departing flights had available seats, let alone which ones were eligible for SkyMile points.
I readjusted my dropped chin and plopped onto a bench in the terminal. I called the phone number on my SkyMiles card and explained my dilemma. My new best friend at Delta loved the idea of The 52/52 Project, but didn’t seem to fully comprehend the idea of that day’s mission.
“OK,” she said. “So, where exactly do you want to go?”
“I don’t care. See, I’m not allowed to choose,” I explained again. “Just tell me the next flight out from Detroit—wherever it is going—which hasn’t begun boarding yet and still has an available seat that is eligible for SkyMiles.”
“Oh.” She paused. A very long pause. “So, I have to choose a flight for you?”
“Exactly,” I said. “Hey, I’m really sorry. Am I putting too much pressure on you?”
“Um, yeah. But, alright, if you truly just want the next available flight, it’s… well, it looks like it’s Fort Myers, Florida.”
I did a happy dance around the terminal.
My celebration was premature. She told me she couldn’t book the flight until the miles were transferred. And that could only be done online.
Did these people not understand my planning anxieties? I needed a boarding pass pronto, so I knew where I was going and when, and could then at least check those rather significant items off my mental list! While I was at it, I also wanted to make a list of every person who had lied or misinformed me about this whole fiasco of a process, so I could file a formal complaint.
I plopped back down on the bench. Sure, I had both my iPhone and my laptop with me, but I knew my best bet was to call Son #2, the techno-geek in the family. He was surely sitting in front of a computer and could manage the entire thing faster than I could even look up the web site. But he kept getting error messages, and a half-hour passed with no progress.
Just as I began to feel certain the flight would begin boarding before I was booked and I’d end up on the next flight instead (it would inevitably be Fargo), my confirmation flashed across my phone. Happy dance resumed! I collected my boarding pass and raced through the airport.
Next up: Finding a hotel. As I rode through the terminal’s seemingly endless series of moving sidewalks, I searched on my iPhone. Huh. Apparently, Florida in March was a popular destination. Thanks to spring breaks, most hotels were either full or charging prime rates.
Finding I still had 30 minutes left before boarding time, I stopped for a Bloody Mary. Did I mention my deep-seated fear of flying? One Bloody Mary generally took the edge off just enough to get me through any turbulence and fears of faulty-engine crash landings. I glanced up at the TV in the airport bar and watched a breaking news report about a missing Malaysian plane. Maybe I’d suck that drink right down and order another.
Meanwhile, I called my sister, DC, a travel guru. Within minutes, she texted back with information about a single room available at an oceanfront hotel in Fort Myers Beach. Although I’d stayed there years ago and knew it was terrific, the nightly rate was definitely more than I planned to spend. But, my airfare was covered and only a few decent hotel options remained. I decided to splurge. Wasn’t I worth it? Besides, I wouldn’t have to pay for a single night after my plane crashed enroute.
Thankfully, the flight was smooth and proved eventful only because I found myself seated directly across from a co-worker, and I discovered the woman next to her followed The 52/52 Project. What were the odds? She bought me a Bloody Mary. Between our conversation and the vodka, I never noticed if the plane—or my legs—were shaking.
My hotel balcony overlooked the pool, the tiki bar, and the ocean. It was sunny and 80 degrees in Fort Myers. As I unpacked, I gleefully tossed aside my coat, mittens, and boots.
I spent the next day with old high school friends who drove over from Naples, where they happened to be vacationing when they read on Facebook about my final destination. I hung out that night at the hotel’s tiki bar. The crowd, not particularly warm and fuzzy, was disappointing. After the bar closed, I wandered back toward my room to sit on the balcony.
After a while, I heard a group of people talking and laughing by the pool. The introverted and unmotivated part of me felt compelled to sit tight. But through the past several months, I’d learned that pushing myself and taking a chance often paid off. So, I headed back down and invited myself to their little group.
Out of everyone I talked to that weekend, these six guys and the one young man’s girlfriend—all of whom were twenty-something and Muslim—were the best folks I met. Much like the Stranger Party I hosted a few months back, this evening proved that new friendships don’t always require having a whole lot in common.
Other than these couple of social outings, I spent the weekend simply walking the beach and gorging on seafood. But was there really any better plan of action for a Florida vacation? Besides, I figured how I spent the trip was far less important than how I’d planned—or more specifically hadn’t planned it.
Although I had originally expected to return home on Sunday, as soon as I learned I’d been blessed with a warm and sunny setting I scheduled my return flight for Monday. It never crossed my mind that this would be St. Patrick’s Day, and that a St. Paddy’s parade would be marching down the street right in front of my hotel.
My taxi waited for me about a mile up the blocked-off road, yet I figured I was nearly obligated to watch the parade. I stopped along my walk to the cab to take some photos with the crowd and mingle with the crazies. The morning could have only been more delightful if I’d had time for a green beer or two. I’d settle for a Bloody Mary on the plane home.
When I made my list of potential 52/52 experiences, this impromptu adventure appeared to be my most half-assed idea ever.
For the new me, who has learned to let so much roll off my shoulders, that made it the best—by a sky mile.
Maybe the very best plan is no plan at all.
Are you a planner or an off-the-cuff sort? What's the last vacation you took and loved? If you headed out on a mystery trip, where would you hope to land?