I Went to Jamaica for Country Music and Got Too Relaxed

You know what else people just do? Go to Sandals resorts. You know the ads on television, with the sparkling bright blue water and swim-up bar and the promise of more, more, MORE? Where you're encouraged to do absolutely as much of nothing as possible, just swim in water and drink a lot of differently colored drinks that are mainly rum-based, sometimes doing both at the same time? In real life it's exactly like that, like Margaritaville on quaaludes, and the only difference between the two is, in real life, pretty much all the people there are in their 50s and thoroughly middle class. This is a Sandals Resort, a romantic retreat for adults only. If you have kids, you take them to Beaches resorts, so that they can also relax, I presume. But I wasn't there to relax, or at least I didn't plan to be.

CMT had flown me there to check out "Story Behind the Songs," a series in which both established and new major label country artists travel to various Sandals and Beaches resorts and perform intimate, acoustic sets for guests. Most have paid anywhere from $45 to $125 for the experience, on top of however much it cost to get there, while others were there after winning a contest, and the rest of us were mostly radio or online media. Once I arrived at the airport, I was swept straight into a Sandals Resort receiving bay, which looks more like someone stuffed a furniture showroom into a bodega and provided free Red Stripe. The wifi password, "time2relax!" ended up being more of an order than permission. There was a lot of focus on relaxing. Relaxing is a big thing at Sandals.

Country music has maintained a close relationship with islands and their beaches for at least 40 years, ever since Jimmy Buffett's "Margaritaville" helped guide people into a soft rock, nautical-themed retirement. Everyone from Florida Georgia Line and Blake Shelton to Kenny Chesney, Toby Keith, and Zac Brown Band have sung about the healing effects of islands and their waters. George Strait has even been known to sing about it a time or two. This focus on island destinations is thoroughly rooted in middle-class escapism, making a place like Sandals a perfect partner. This event seemed by far to be the "freshest" of its kind. It featured three acts—the James Barker Band, Lauren Alaina, and Kip Moore—two of which have found chart success thanks in no small part to the path set down by Florida Georgia Line and their bro-country brethren. Alaina, on the other hand, seemed to be the tomato on the salad inclusion for the trip, though her performance would prove to be the best of the three.

As soon as I arrived at the resort after an hour and a half of my driver Grant navigating winding mountain roads and passing semi-trucks, I was offered a cold towel. For whatever reason I decided that would be a step too far, that I would cross some kind of line because I wasn't technically there to enjoy myself, so I declined with a smile that probably looked like a grimace. Grant must have used my distracted state as a getaway because when I turned to look at him for some sort of behavioral cue that being handed an ice cold towel is a totally normal thing that happens here, he was gone. For a fleeting moment I wondered if it he was thinking about me what I was thinking about all the other guests.

It was time to relax. I was given a glass of champagne by one woman while another woman checked me into my room. A young man gave me a tour of my room which I think he and I both silently agreed was completely absurd since I was there by myself. He made a point to tell me all of the food and alcohol was provided free of charge. All of it, he repeated. "All of it?" I asked, not totally believing him. Yeah, all of it, he said back.

At this particular Sandals resort there were three different living experiences which are known as "villages:" French, Dutch, and Italian. My room was located in the French Village. There is a "main piazza" and a "beach piazza" where the food and fun portion of relaxing happens. There's a pool with a swim up bar, a jerk chicken shack, a French cafe, Italian restaurant, a Caribbean place, and a sushi restaurant with its main claim to fame being that it was on the sand. I was booked in a smoking section but they didn't seem to be enforcing it, because Dan and Linda, my neighbors and huge Linkin Park fans, were smoking when I went to try to bum a cigarette. (This was my plan for the next three days: Bum as many cigarettes as I could as an excuse to talk to people. Either Dan and Linda noticed this plan right away or Canadians are in all actuality kind people because 20 minutes later I returned to my room with half a pack of unsmoked Canadian cigarettes.)

My room was incredible. Definitely way too small for a couple, but just big enough for one person. It was on the ground floor with a private deck opening directly onto a jacuzzi that could hold ten people at a time. When you opened the sliding glass doors doors, the A/C stopped running. When you closed them again, the A/C turned back on. It was awesome.

Around 7 PM, only an hour from the performance, it began raining harder than I've ever seen, but it only delayed the show an hour. Within five minutes of it stopping, the resort staff had replaced—not just flipped or toweled off, but replaced completely—around 20 wet couch cushions and at least 100 white plastic lawn chairs. Wet floor signs were erected and the plastic tarps covering the bars were taken off, making the area look almost as if the weather had never happened. While headliner Kip Moore played "Plead the Fifth" off his then unreleased album Slowheart, lightning lit the sky all around him.

Joining Moore at this event were Canada's James Barker Band, who just broke several records on the Canadian country charts previously held by none other than Shania Twain with songs like "Chills" and "Lawn Chair Lazy," the latter of which features an annoyingly catchy chorus that repeats the word "beer" three times in a row. When introducing the song, lead vocalist James Barker showed his Canadian heritage saying he didn't think they could write a song for the country music genre that contains the word "beer" three times in a row.

Lauren Alaina followed the guys, prompting host Cody Alan to comment on her body and introduce her with a resounding, "The great thing about Lauren is she's more than booty!" The Georgia native who made her public debut as runner-up on American Idol in 2010 seemed to be the performer most comfortable in front of a crowd. Where Kip Moore claimed he didn't think anyone wanted to hear the story behind his songs, Alaina shared stories of her struggle with an eating disorder, growing up in Georgia, and a crazy family—one of her recent singles "Doin' Fine" starts with the line, "Daddy got sober, Mama got his best friend," which if that ain't country I don't know what is.

The next day, as I nursed a hangover the likes of which I'd not experienced since college while enjoying a frozen rum drink at the swim up bar in the main piazza, a DJ led some of my fellow relaxation heads in a round of the electric slide. At Sandals South Coast everyone is so relaxed, they just do that! I had a full day of unregimented relaxation ahead of me, and baby I was going to take advantage of it. I ended up sleeping on a beach chair for most of it. The complimentary wifi was slow, and didn't work outside my room really, so I couldn't be online if wanted to (I wanted to). It was as if the moment I walked in the rest of the world sort of stopped existing. I considered this for a brief second while a guy explained to me what he did for a living—he owns a construction company with offices in three states or something—but before I could take myself seriously one of the staff members showed up to ask if I needed anything and if we were OK, eyeing my empty glass. I thought about it. What, in this literal paradise, could I possibly ever need? Was I OK? Could I ever, here, really need anything? I declined and went back to my room, ordered room service, and took a nap. The next day, when the plane landed in New York, everyone clapped again.

Annalise Domenighini has no idea what relaxin' is. Follow her on Twitter.