Chubbies models slide down a slide together

Chubbies + Kissimmee = <3

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Recently, the team from Chubbies — the popular shorts and clothing brand — decided to take a little trip to Kissimmee. They were interested in showing off their brand-new line of clothing, including swim trunks, shirts, pullovers, zip-ups, and more for the entire family. Plus, with new blazers just to wear while relaxing poolside, they knew they’d chosen the perfect location for the grand apparel line reveal! 

The Chubbies models who visited Kissimmee were winners of the Man Model Search — a competition where over 12,000 worthy candidates submitted their best photos and 10 came out on top. And what better way to celebrate being a newly-crowned model than with a fabulous photo shoot in the sun? How about a new clothing line debuting in the ultimate family-friendly destination? Sounds like a match made in Kissimmee!    

In fact, they had so much fun showing off their trending swag — they've decided to give away an unforgettable Kissimmee vacation! That's right, you and three of your closest friends and family can win round-trip airfare, accommodations, car rental, theme park and attraction passes, and four pairs of Chubbies shorts to strut your stuff in while you're here!

Our week with Chubbies can be summed up in a few fabulous words: colors galore, printed shorts, funny memes, and BIG personalities. When the Chubbies team landed in Kissimmee, they were the talk of the town, and we were there to capture every moment of their awesome adventure.

H2-Oh the Places We’ll Go

Men playing basketball together in the pool
Island H20 Live!

On their first full day in Kissimmee, the Chubbies team got their feet wet (literally) with a trip to the Island H20 Live! water park. Their mission? Gather some content sure to make a splash! Luckily, this was easy to do thanks to the park’s amazing water slides and lazy lagoons. And did we mention the Selfie Shack for sharing unforgettable moments from a fun day poolside? 

A mother and child slide down a waterslide together
Island H20 Live!

Chubbies is best known for their swim trunks, and you better believe they were styling and profiling at Island H20 Live!. Bold colors? Yup! Fun prints? They had everything from flamingos to stars and stripes. There were even shorts inspired by a galaxy far, far away. Trust us, the style Force was definitely strong during this photo shoot.

It’s Five O’Clock Somewhere

A Chubbies model at Margaritaville
Margaritaville Resort Orlando

As Kissimmee visitors themselves, the Chubbies team wanted to see as much as they could during their time here. After toweling down at Island H20 Live!, we made our way to the land of umbrella drinks, shimmering pools, and laid-back vibes: Margaritaville Resort Orlando. Of course, with a change of scenery comes a change in wardrobe (along with applying sunscreen and a little hydration), but before long we were back out for fun in the sun!

Welcome to the Crib

Men hanging out by the pool
Eagle Bay Mansion at Reunion Resort

The folks at Chubbies love to go big, so it makes sense that they enjoyed the luxury vacation home pool at Eagle Bay mansion at Reunion Resort. This location is, in a word...amazing! With 10 bedrooms and bathrooms, a pool, a home theater, and even a private lazy river for ultimate relaxation, the Chubbies crew and models loved this place so much that they made it a primary shoot location for their second day in Kissimmee.

The Chubbies team lounging on the lazy river
Eagle Bay Mansion at Reunion Resort

One of the coolest videos from the day was captured by a drone flying above the models as they floated along the lazy river at the vacation home in alligator, flamingo, and pineapple floaties! Naturally, we got in on the fun and made a video starring our very own Experience Kissimmee team member, Ty.

If you ask us, the best thing about choosing a vacation home in Kissimmee is that regardless of your budget, there’s a perfect home-away-from-home to suit your needs. Whether you’re visiting with a few friends or bringing the entire extended family, you’ll find out first-hand why Kissimmee is the Vacation Home Capital of the World®.

You Slide, I Slide, We All Slide Together

Chubbies Models Goofing Around
Omni Orlando Resort at ChampionsGate

From Eagle Bay, we made our way to Omni Orlando Resort at ChampionsGate take some epic water slide photos and videos. This resort features four pools, a lazy river, and a wave pool, so our afternoon was spent “pool hopping” and trying to make a splash in every body of water at least once (#VacationGoals)! The Chubbies models were posing, sliding, and (of course) being total goof balls.

Exploring Celebration

The Chubbies team rides their bikes through Celebration, Florida
Celebration, Florida

The next day, we ventured to Celebration, a picture-perfect town full of beautiful homes, quiet neighborhoods, and biking trails just waiting for exploration. That’s exactly what the Chubbies team did during their visit, thanks to a little help from Celebration Bike Rental. They took a relaxing pedal tour around the town, decked out in their snappy shorts, dapper daywear, stylish shirts, and playful pullovers. The models definitely turned some heads — but that’s to be expected when you’re looking stylish and having the best time ever with your friends!

Taking Chubbies Down the Old Town Road

Chubbies models enjoy an ice cream at Old Town Kissimmee
Old Town Kissimmee

For our final day with the Chubbies team, we visited one of our favorite local spots — Old Town Kissimmee. Here, we spent the afternoon and evening full of snacks, shopping, and snaps! We stopped by the local ice cream parlor for some cones, took a few photos in the classic cars, and sipped on some ice-cold drinks. To cap it all off, we took a spin on the Ferris Wheel, taking in the fantastic views to end a fantastic visit.

Island H20 Live!

Our week with the Chubbies team was full of adventure, laughs, and short shorts — and it’s a week you can easily have as well! Whether you want to hit all the spots the Chubbies team visited or branch out and explore all that Kissimmee has to offer for yourself, we can help. Check out our trip planning tool, and subscribe to our newsletter for even more awesome vacation ideas.  

And in the words of our new friends at Chubbies, “Onward to the weekend!”

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