I wasn’t supposed to be traveling to Anguilla alone. Two other women were originally part of the plan, but they bailed, leaving me with a decision: Should I go on the trip alone or cancel?
At 52, I’m not a natural solo adventurer. I’m the type of person who is nervous about approaching others to take my picture or ask for directions. I’ve never eaten at a sit-down restaurant by myself. Sure, I’ll grab a quick sandwich alone, but a “table for one” that requires admitting my status to a hostess? No, thanks.
I only began to waver when I realized that Anguilla would be my 12th Caribbean island. Apparently, I am the type of person who will endure social anxiety for the sake of a good travel statistic.
But there was another reason I wanted to go. With my youngest preparing to fly the coop for college next year and her two older siblings already halfway through their degrees, the reality of an impending empty nest was looming. My house was about to get very quiet, and I realized I had no idea if I knew how to be alone. This trip was a test drive for my next chapter.
I felt the freedom before I even made it to the island
Once I decided to go, I started packing. It was shockingly easy.
For the first time in two decades, my mental checklist didn’t involve anyone else’s survival. I didn’t have to track down my kid’s Dramamine — a mistake I’ve made before.
I didn’t have to hunt for my husband’s favorite hat, the absence of which once left him with a sunburn I had to hear about for the rest of the vacation.
Dare I admit that it was fun to pack by myself — and liberating?
That same sense of freedom followed me onto the plane. Usually, my flights are spent acting as a high-altitude IT department or a concierge. Not this time. I didn’t need to worry about anyone’s hunger or dying iPads. I also definitely didn’t miss lugging five suitcases through the airport.
Courtesy of Cheryl Maguire
Instead, I sat back and watched “The Real Housewives.” For the first time, I could enjoy drama on the screen without having to manage any in the seat next to me. As we hit cruising altitude, I realized that this solo trip wasn’t just a bold move; it was a game changer.
I sat down at a table for one
By the time I checked into my hotel, it was already dark, which meant the beautiful turquoise Caribbean water was hidden from view. Disappointing, sure, but after escaping the Boston snow, the warm tropical air was enough to keep me from complaining. I reminded myself that the view would still be there in the morning.
For dinner, I ventured out to a local restaurant. As I approached the hostess, I braced myself for the dreaded question I knew was coming.
“How many in your party?” she asked.
“Just me,” I replied.
To my surprise, I didn’t feel awkward or sad. But after I ordered, the anxiety crept in. I glanced around at nearby tables, seeing families or couples conversing, and for a moment, I felt that pang of loneliness.
But then my meal arrived. Once I took a bite of the duck fillet, my discomfort dissipated. When you aren’t busy talking with others, you actually taste the food. The meal was so incredible that I stopped worrying about how I looked to the other diners and enjoyed the experience.
I also enjoyed my alone time on a small island
While in Anguilla, I took a day trip to another island — a tiny sliver of sand with a grill and a few chairs. It’s so small that you can take in the entire coastline without ever having to leave your seat.
During my three-hour stay as a voluntary castaway, there were only four other guests plus the kitchen crew. If I had my husband or kids as a social crutch, I would have stayed planted in my lounger.
Instead, I talked to the other people on the island. I even worked up the nerve to ask them and several others I met throughout the trip to take my picture. Normally, I would rather go without the photo than endure the awkwardness of asking a stranger, but traveling alone had forced me out of my comfort zone. Who knew being a castaway could make me more social?
I’m now ready to be an empty nester
What happened on that trip surprised me. Traveling solo helped me realize that I enjoy being alone and that I can strike up conversations with strangers.
My house is about to become noticeably still, and I’m going to miss the constant singing of my youngest echoing through the rooms.
But thanks to those solo days in Anguilla, I know that when the music stops and the last suitcase is packed for college, I’ll be OK. Instead of fearing the silence, I now find it peaceful.
I might even book a table for one.
