My First Solo Trip
My First Solo Trip
Location: The Gloucestershire Hotel, Montego Bay, Jamaica
In early April of 2004, I found myself burnt out and desperate for a proper get-a-way. My requirements were simple: unchartered territory, warm and, most importantly - affordable! I started my search on the internet looking for last minute deals to destinations with open inventory and deeply low prices. I wasn’t looking for a 5 star hidden gem, but a practical location that permitted me to escape when I needed to. I should also make note that at this very time I was crushing on a guy who was not that into me and I needed a break from the dance of unrequited infatuation.
During this time of my life I was single, my friends were busy with heavy work schedules and new relationships and I found myself struggling to find a travel partner, especially one who was willing to be as spontaneous as I was, and able to haul off last minute on an adventurous trip.
Committed to get away, I decided to submit a couple vacation days to work, take the Thursday and Friday off to have a long weekend away, leaving my trip up to the fates. With only a week to spare before my committed dates, it happened! On my searching for any last minute excursions - an all inclusive resort, flight included, appeared! Total cost was less than $1,000. The Gloucestershire Hotel in Montego Bay, Jamaica it would be. Booked and ready for action.
The purchase was made and the first thought to cross my mind was, how my friends and family would react to my solo travel outside of the country at 23 years old. My desire for time away was to great. A hot beach out-weighed all my negative thoughts or perceived judgment from my friends and family. The best part? Booking a trip within a week of leaving, you don’t have a ton of time to worry about other’s feelings on your life.
I packed my little carry-on and headed to Newark Liberty International Airport, Jamaica-bound. I arrived at Sangster International Airport near Montego Bay, to the balmy island air and made my way to customs. As I cautiously slid my passport over to a large, serious, dark, female customs agent, her eyes traveled back and forth to my passport and to me. With immense focus and eye contact she asked and our dialogue began.
Agent: “Are you travelin’ alone?”
Me: “Yes.” I replied quickly and careful not to make any sudden movements.
Agent: “Yah nah gon’ be bored?”
Me: “I sure hope not.” She slides my passport back to me.
As I walked away from the booth I thought to myself, will I be bored? It was the first time in a long time, far away from home, I would be spending quality moments with myself.
On the hotel shuttle I climbed and alone with the driver we made our way to the little humble yellow hotel situated across the street from Doctor’s Cove Beach in Montego Bay. I made it! I couldn't believe it. I was so psyched and proud of myself. After reviewing my documents and checking in, I immediately dropped off my bags and ran to find a bathing suit. In all of the hurried planning I forgot to buy one and ended up with a hot pink Brazilian style little two piece. You will note there are no photographs of me in this number and I no longer have it in my bathing suit collection. But at the time I was thrilled to have something appropriate for the beach. I couldn’t wait to change and hit the sand. Of course at this age, before anti-aging and skincare was anywhere on my mind, sun worshipping was everything to me.
Between laying in the sun, browsing the local shops and merchants’ goods, reading, writing, getting my hair braided, taking photos and making friends with the locals, it never crossed my mind the doubt the customs’ agent shared with me about my chances of becoming bored. Weaved in with time with myself, I made friends through very creative and bold ways. Making friends on a solo trip, in a foreign country... deserves it’s own blog post.
With all of the back and forth from my room to the beach to the buffet to the pool, I made many trips through the lobby area which allowed me to become acquainted with the hotel security guard on duty. For the sake of this tale, let’s call the security guard, Kirby. Kirby was young with a kind face, a native of a small town called Dumfries. Kirby granted me the opportunity to explore non-tourist sites on the island - the key to a successful trip are hidden gems. Kirby’s willingness to spare his afternoon to show me his home was the icing on the top. He instructed me to attempt to blend in. I wore my hair down, tied up my sneakers and buttoned my jeans. Humidity was at an all time high - like 1,000%.
We started our journey towards Dumfries filled with local customs and music while passing miles and miles of sugar cane. After arriving to town, we pumped water from a well as I has grown thirsty, walked the streets of dirt roads lined with shacks, ate stew from amazing cooks in long red aprons in a shanty town and let the melodies of reggae music float around my ears. It reminded me of the island life I grew to know while visiting my mom’s family in Puerto Rico. Different customs, traditions and languages, but similar energy and community dynamics on the islands.
After a long afternoon of exploring, night began to fall and Kirby drove me back to the Gloucestershire. On our ride home, I distinctly remember how dark everything was around me. As we made our way back, passing the fields of sugar cane, I decided to open my window and stick my head out to stare at the night sky. Time stood still. It was the most magnificent night sky I’d ever seen and holds that title to this day. The lack of light pollution allowed the most perfect view of each and every star. Each one had a twinkle and celestial dance. My eyes teared from the wind whizzing over my face. I didn’t want any of it to end. I prayed it wasn’t a dream.
When Kirby dropped me off at the hotel he gave me his phone number, asked me to stay in touch and let him know when I returned to the island. I told him I would, but to date I still haven’t been back to the Gloucestershire or anywhere in Jamaica.
That night, my last night, I had some the best sleep of my life and when I arose the next morning, my last morning, I was thrilled to enjoy endless cups of Blue Mountain coffee. Recommendation: Drink Blue Mountain coffee. Amazon and online shopping exists for this exact reason. Don’t deprive yourself. If you haven’t had it, I want to let you know it's some of the best coffee in the world.
As I returned to NJ, sadness fell over me as though I left a part of me back on the island. I needed time to mourn the loss of the most special discovery. After time and reflection, my sadness turned to gratitude. I never left anything behind, but took with me an experience that was unparalleled and all uniquely mine.
My only wish was to return to the customs agent and let her know I was never bored and remind her spontaneity is the spice of life and travel is whatever you make it to be. Once she rolled her eyes at me, I would continue with reminding her to never hold back, feel fear of the unknown, or wait for the perfect time. It may never come. Life is waiting for you to make it happen and requires you to prioritize a goal or dream you have for yourself.
Incidentally, while I was away that second to last weekend of April, that I guy I had a crush on ended up on a date with a woman who today is his wife. It’s amazing how the fates work. It always seems meant to be.