Pop2000 in Paradise

Date: September 27th - October 4th 

Location: The Fives Resort, Playa Del Carmen, Mexico

Pop2000 in Paradise was my first trip to Mexico. This trip, organized by Vacation Jams, was definitely the 2023 MTV Spring break for grown adults in Playa Del Carmen, Mexico. 

The Pop2000 in Paradise is an all-inclusive package containing 5 hotel overnight, food, drinks, hotel/airport transfers and access to all the Pop2000 events.The multi-day event featured O-Town, NSYNC’s Chris Kirkpatrick, Billy Gilman,  LFO, Ryan Cabrera, David Cook, Carl Wockner and comedian Marcus Monroe.


The Fives Beach Hotel and Residences

The prime location of Pop2000 in Paradise was at  the Fives Beach Hotel and Residences, approximately 40 minutes from the Cancun airport. 

The Fives Resort is a beautiful exclusive location situated between the beach and the jungle. The hotel had multiple pools including an infinity pool near the beach and an adult private pool near our villa. The resort also provided gym and spa services. I definitely took advantage and  got myself a full massage and aromatherapy treatment. 

The property is just massive with a sprawling jungle! We definitely got our steps in walking around the resort.  

Moreover, the Fives staff provided great hospitality. The staff were willing to help guests with anything they needed to better their stay. 

My friend and I booked a one-bedroom suite with a kitchen and living/dining area with a balcony facing the jungle. The suite was definitely the perfect size for two people staying in a one-week stay in Mexico. From our suite, we could see monkeys and possums moving about in the trees. One possum, whom we called Poppy, occasionally claimed our balcony as his resting spot. 

We definitely lucked out with the weather too. During our stay, we had clear sunny skies the majority of the time. It only rained either overnight or for 5 minutes in the early morning. 

Pop2000 Theme Days


I was grateful that Vacation Jams organized a well-spread out program schedule with the day activities starting at 12 pm and ending at around 4 pm.Then the night activities starting between 8-9 pm. Definitely provided ample time for guests to rest (recover), go to the gym, take some personal time, relax, eat and get ready for the next event.  Each event was DJ’ed by DJ Xcel.

Each day contained a different party theme where guests were encouraged to dress up in costume.

For example, on the fourth night,  Pop2000 hosted a 90s/2000s theme night. People dressed up in the overalls and bright colored clothes popular of that era. On top of that, the pool was filled with foam and bubbles. People were either chilling by the bar area or swimming/getting lost in the foam. During the night, Carl Wockner played an acoustic set and Dan joined in on a song or two. 

On the following night, Pop2000 hosted a White-Out party where guests dressed up in full white outfits and danced all night.  Ryan served as the guest DJ.

The last night was Superhero night where everyone dressed as their favorite Superhero. I dressed up as Spiderwoman. That night, Billy Gilman debuted his upcoming single, “Delta Queen”. Trevor, who is in the process of pursuing acting, tried out his comedic stand up routine. He was actually quite funny especially when he talked about his upbringing as a mixed race kid. Later, comedian Marcus Monroe performed his hilarious stand up. He even juggled random objects.    

Karaoke Night

One of my favorite nights was definitely the first night in Mexico. We had a “Dress up as your favorite Boyband” theme night. Certainly one of the easier theme nights. I figured I could get by dressing up in double denim and a NSYNC t-shirt and hat. And coincidentally Trevor and I matched! 

Trevor definitely was the life of the Karaoke night. He kicked off the party with singing Nelly’s “Ride with Me” and energized the audience. He and Dan karaoke’d to Jagged Edge’s “Where The Party At”. He even dressed up with an umbrella and wig and danced to “It’s Raining Men!” with two other fans. 

I ended up going up to sing “What Makes You Beautiful” with Trevor. Never in my wildest dreams that I would karaoke a One Direction Song with a member from O-Town! Trevor’s energy and motivation definitely made me more comfortable and confident to sing that song on stage. It was super fun! 

I also did not expect to see Billy, Ryan and Jacob to  karaoke at the Village People’s  YMCA. The sight was ludicrous to watch. 

My favorite part of the night though was watching Dan’s daughter, Navy sing Olivia Rodrigo’s Traitor. The girl can sing with so much heart and emotion for someone who may have not experienced teen heartbreak yet. It was just a very special and sweet moment of Dan singing with her. Navy definitely inherited her parents’ talent! 

Finally, what made that night extra special, Chris Kirkpatrick played a preview of the new NSYNC song, “Better Place” off the third Trolls movie. The room was definitely filled with nostalgia and excitement finally hearing a brand new NSYNC song after 21 years! Everyone was dancing and feeling giddy. The song is amazing, especially hearing JC’s beautiful voice. The best part was 8 hours after the “Better Place” release, the song went to number one on iTunes! That morning, I ran straight up to Chris and gave him a big hug! 


Acoustics Pool Party

My other favorite day was the Acoustic Pool Party on the afternoon of Day 4. It was just a relaxing day by the pool. The weather, though very hot, was sunny, bright and clear. 

We mostly chilled on the beach chairs while David Cook and O-Town each performed a setlist of songs. Both sets were stripped down performances with just the artists and a guitar accompaniment. 

David sang his songs “Fire” and “Lie” as well as his American Idol victory song, “Time of My Life”. This was the first time I saw David perform live and he definitely delivered. He has such a strong and deep voice. I also felt the emotion during his performance. He can clearly connect well with the audience. David also joked it was his first time performing in an all white outfit and shorts directly under the sun. 

O-Town appropriately performed “We Fit Together”, evoking the feeling that we are in that 2001 music video on the yacht. David joined them playing on guitar. They also performed “Suddenly”, “The Joint” and “Been Around The World”. Despite the heat, the boys’ harmonies and voices truly shined. It was nice to see them relax, enjoy the atmosphere and just sing and engage with the crowd.  


Pop2000 in Paradise Beach Concert

The biggest highlight of the whole trip was the Beach Concert on the second night. The concert was a full four hours, clearly one of the longest concerts I’ve ever been to. And it was the first time I’ve ever danced to live music barefoot on the sand! 

The show kicked off with David Cook’s performance. He sang his own rendition of Mariah Carey’s “Always Be My Baby”, one of his American Idol performances. I remember watching him on the TV back in 2008. I can say the in person live version is obviously better. David also sang a wonderful version of Prince’s “Purple Rain”. 

After David, Billy came onto the stage. He first sang his song, “Good Life”. Next, he delivered a beautiful version of Michael Jackson’s “Man In The Mirror”. My favorite, though, was his Voice winning performance of “I Surrender”. Billy really showcases his vocal range within the song. Billy mentioned that he spent days convincing his voice coach, Maroon 5’s Adam Levine, to perform “I Surrender” on the show up to moments before the Voice Finale. 

Ryan Cabrera performed next. In addition to his classic songs, “True” and “On The Way Down”,  and “Wherever, Whenever”, Ryan debuted his upcoming single, “Prescription of You”. He closed his set by playing his rendition of One Direction’s “What Makes You Beautiful”. Definitely better than my Karaoke version! 


Finally O-Town performed, kicking off the show with “Liquid Dreams”. The boys were dressed up in Pirates baseball team uniforms. They followed up with “Off”, “We Fit Together” and “These Are The Days”. Later, Brad joined them onstage to perform to celebrate the LFO legacy with songs like “Westside Story”, “Girl On TV” and “Summer Girls”. O-Town continued the show with their song, “Giants”. 

Similar to their Pop2000 tour format, Chris joined the boys onstage for an NSYNC medley, starting with “Bye Bye Bye”. They also performed “It’s Gonna Be Me” and “Pop”.

O-Town definitely showed their exhaustion as the show progressed. At some point, David Cook had to bring out a big bowl of ice for Jacob to dunk his head in. Despite their burnout, the boys still carried on and their harmonies still stayed consistent. 

The O-Town boys finally closed the show with their major hit song, “All Or Nothing”. They made the performance extra special by inviting Chris, Billy, David, Brad, and Joe onstage to sing with them. It was the perfect way to end the night. You can definitely feel the brotherhood and camaraderie amongst the group of guys. 
Overall, I truly had a wonderful vacation. Pop2000 in Paradise was definitely the escape I needed. I’m so glad I went and savored every moment of it!  I am thankful I made new friends during this vacation. I definitely will state that the vacation is totally worth the price. The majority of the O-Town members came to all the scheduled events as well as Ryan, Billy, Chris and David and Marcus. Overall, I saw the boys every day since we were all staying in the same resort. In fact, Dan and his family stayed in suite two floors above me and my friend. We jokingly called Dan our house mate.

The vacation was a great mixture of music, fun and relaxation. I’m excited that Pop2000 in Paradise will happen again this year! Shout out to Ryan Trenn and Joe Bachman and the Vacation Jams team for making Popo2000 in Paradise a success!














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