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What I Learned From My Romantic Vacation Alone

Don't get me wrong, I love to travel with friends, family, or with a lover, but I am so happy I experienced a solo trip, and I'll definitely do it again (though next time I'll probably pick a spot that's less packed with honeymooners).
05/23/2016 10:11am ET | Updated December 6, 2017
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USA, New Jersey, Woman ready to go on vacations

It was a bitterly cold night in Brooklyn, late in March 2014 when, coming off a brutal winter season, I was sick and tired of the constant snow and windstorms. I sat on the floor of my teeny tiny studio apartment and curled up with blankets, pillows, and a Hot Toddy to work on the cookbook I had started writing. I couldn't get focused that night, a little because of writer's block, but mostly because I was itching to get the hell out of freezing cold New York.

While on a phone chat the night before with one of my best friends she mentioned that her coworker was starting up a side business as a travel agent. So, as my mind was wandering in my room, I got curious about where her friend might have connections, and next thing I knew I was zoning out hard to a vision of myself sprawled out on a beach chair next to a turquoise blue pool, somewhere sunny and tropical, and oddly enough, with no one else by my side. The vision was awesome, but I almost immediately started worrying about being judged for being alone.

It seemed utterly crazy to consider booking a vacation by myself, without consulting anyone or inviting someone to come along. Just me. I was scared of people judging me for going alone or not having anyone to invite. I also didn't want to tell anyone at first because I felt guilty for spending money on a vacation by myself. I've never felt like I had extra money, and it made me uncomfortable to think about how others might judge me, even though I knew in my heart I deserved a retreat and a time to rest. I remembered the promise I made to myself the summer before - the Notorious Summer of 2013 when my dad died, I got dumped, I sprained my foot, and damn near lost my mind. When I made it through that mess I promised myself I'd do more of what I wanted and less of what I thought others expected me to do.

Letting the memoirs rush over me, I suddenly I understood with my whole body, goosebumps on my arms, that it was more important to me to take care of Me, the one who knew I how hard I had worked, who knew all the bullsh** I just went through, who knew the crazy hours I'd been putting in, and who knew I absolutely deserved to go on a resort vacation. It was more important to listen to Me than to back down to the fear of judgment from anyone else, no matter if they were the people I loved the most or complete strangers. Who knows? Maybe they'd even support me?

Five minutes later I had my credit card in hand, and was dialing my friend's travel agent coworker, apologizing for calling her at nearly 10pm on a weeknight. "So...I want to go somewhere tropical for about 4 or 5 days in June. Yep, just me (nervous laugh). I need to be somewhere where I'm safe by myself because I'm not inviting anyone (another nervous laugh). The only thing I want to worry about while I'm there is if I should order another piña colada or take a nap before jumping back in the pool. You feel me?"

The travel agent seemed more excited than I was. "Wow, so you're looking to go all alone?! That's so gutsy! I would love to do that someday. Okay, let me work up a few options for you and I'll send them over first thing tomorrow morning." My reply, "um...OK...that sounds perfect."

By the following afternoon I had booked an all-inclusive trip to a resort in Montego Bay, Jamaica for 4 nights and 5 days. But, the second I saw the confirmation in my email I got very nervous. My ego took center stage with all the reasons I should turn back now: "I should have thought this through for at LEAST 24 hours first...People will think I'm a loser for vacationing alone because I'm single...My family is going to judge me for spending my money...Who the hell do I think I am?"

I took a breath and remembered the vision of myself poolside. Yes, it would all make sense once I was there, right? I buried the fear and spent the next few months working my two jobs and finishing up my cookbook. The day to leave for vacation snuck up on me quicker than I could have imagined. The morning of the trip I packed one bag full of swimsuits and maxi dresses, hopped in a cab, and headed to JFK airport to board my flight to paradise.

Within a few short hours I was in a tank top and flip flops, nervously waiting for my scheduled ride in a parking lot behind the airport in Montego Bay. I was thrilled to be far away from chilly NYC but definitely scared to be that far away from anyone I knew. Admittedly, I love going to the movies or dinner by myself, but I knew it was taboo to go on a trip alone, especially to a romantic beach resort filled with honeymooners.

I made it to the resort in less than an hour, checked in at the desk, sent a few "I'm here, safe" texts to family members, and made my way to my room right as the sun was going down. I dropped my bags and quickly flung open the curtains and sliding glass door of the room to check out my view. I let out a big sigh, grinning at the two sparkling turquoise pools below me, the ocean spread out for miles, and the salty smell of the beachy air in my lungs. Getting there took some guts, but I was so proud of myself for taking the leap. I felt a mixture of energized and exhausted.

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I spent the next 5 glorious days in Montego Bay doing sipping frozen piña coladas, reading crime thriller novels, working on my tan, eating copious amounts of passion fruit, and watching the sun rise and fall over the ocean. I felt a sense of pride for taking the time and money out to take care of my own wants and needs. I also felt more calm and present that I had in years. There were gorgeous times where I did noting for hours on end but sigh, take in deep breaths of the ocean air, and drift in and out of dreams on my beach chair.

But, there was also a healthy share of tender moments. While I allowed myself to relax on the trip, the stillness crept up on me after a couple of days, and I became intimately aware that I was alone. Not just alone on vacation, but alone in the world, about to embark on a journey as a single woman in her 30s. It was mostly hard at night, and I cried myself to sleep a few times. It wasn't that I was sad to be there, or sad that I was by myself, because I was thrilled to be on vacation at a gorgeous resort! It was that I finally had the space to be still, to be alone, and to feel my feelings, to remember and let go of more of the pain I'd just been through in the last year. On this trip by myself I didn't have to be strong for anyone, especially me. So I cried, and I breathed, and I cried again.

Some meals I felt lonely and ridiculous, and had to put on a brave face when the cute waiters at the restaurants teased and flirted at me with their favorite one liner: "Aww honey, where's your boyfriend? Oh, you're alone?! Don't you worry, I'LL be your boyfriend for the night." Couples and families sneaked glances over at me, and I imagined people feeling sorry for me, wondering if there was something wrong with me. Was I left at the altar? Was I in therapy? Why in the hell was I there all alone? I tried to avoid eye contact when I could and did a lot of staring at my food or out the window. God, I felt so awkward. It was one of the parts of my trip I knew would be tough, but it was actually harder than I had imagined. I fantasized about just going back to my room and ordering room service for every meal, but I refused. Damnit, I was on vacation and I deserved to have the nice meals in the fancy restaurants.

There were also times when no one talked to me and I ate in glorious, perfect alone-time silence, sitting at the far end of the restaurant nearest the ocean, soaking in the seductive, gentle sounds of the waves that massaged the shoreline at sunrise and sunset. In those moments I wouldn't have changed a single thing, especially the fact that I was all by myself. There was a real a mix of highs and lows, and I'm grateful for all of them. I spent 5 days with me and only me, and by bolding investing in myself, I realized I deserved to start spending a lot more of my own attention and hard earned money to heal, breathe, and love myself through my joys and pains.

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If you're thinking of venturing out alone, I commend you. It takes major guts to go on vacation by yourself. Before you leave, friends and family will probably nervously ask why you're going alone, what you plan to do all day, and plead with you to be safe. You can't seem to avoid those awkward conversations (believe me, I tried). While you're on the trip, the same questions come up. It's hilarious how many times I heard the line, "what's a nice girl like you doing in Jamaica all by herself?" or "OMG is this your version of How Stella Got Her Groove Back?!" or "So, where's your husband?" As uncomfortable as those moments were, going alone felt like a fun social experiment, and I was proud of myself for trying it. As hard as it was, I felt accomplished eating dinner, drinking, and floating around in the pool all alone. Honestly, why are we all so scared to spend time with ourselves and to spend time ON ourselves? When I could relax and let go of the fear of judgment I loved my solo company.

When you're traveling alone you get to do exactly what you want. Want to over-indulge at the buffet? Do it. Want to go to bed early instead of partying or going on planned tours or excursions? Do it. Want to read frivolous books by the pool for 8 hours with no one bothering you? Do it. Taking a trip on your own might be the first truly relaxing vacation you've ever had. I recommend that everyone go on vacation by themselves at least once, even if you're scared, even if you think you can't afford it, especially if you think you don't deserve it or don't have time.

Getting away from your everyday environment removes the distractions and comforts of your social circle and family members and reminds you of what you truly want and need. On my trip I re-discovered my diehard love for naps, remembered that my introverted self desperately needs daily pockets of quiet time, and realized that living by the beach boosts my creative energy and love of nature. It also helped me get out more of the pain and anger I'd been holding onto from the summer before.

Don't get me wrong, I love to travel with friends, family, or with a lover, but I am so happy I experienced a solo trip, and I'll definitely do it again (though next time I'll probably pick a spot that's less packed with honeymooners). My fear of going alone taught me that traveling alone was not only something I really wanted to do, but it was also guiding me to learn how to make more decisions from my gut and less from my ideas about what other people might think. My biggest lesson from the last few years has been that if I'm scared of something, it means I need to dig deeper, follow it, and find out why.

The mix of joys and discomforts on my solo trip was a beautiful surprise.

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This is an excerpt chapter from Laurel Moll's upcoming memoir Following Fear: How I Faced 30 Fears and Learned to Trust the Unknown. Find out more at LaurelMoll.com.