Meet The Judges

During October, all entrants will be judged by an internal panel at CheapCaribbean. They will review all submissions for completeness, then narrow to the top 3-5 resorts in each category. The top resorts in each category will then be judged by 4 external travel and lifestyle bloggers.


Caitlin Palumbo

Caitlin Palumbo is a travel blogger and photographer at My Darling Passport, where she features colorful adventures and bucket list destinations in the U.S. and abroad. She started My Darling Passport as a way to share her passion for travel and adventure, and to inspire others to get out and explore the globe. Caitlin lives in New York City and holds a master’s degree in journalism from Columbia University. You can follow her adventures on My Darling Passport and on Instagram at @MyDarlingPassport.



Hannah Rheaume is the content creator behind her travel blog, The Sunny Side of Things. Her home base may be Portland, Maine but she’s been traveling around the world, full time, since 2016. Hannah’s main focuses are luxury adventure, exotic destinations, wilderness escapes and storytelling.



Lauren Meeker is an avid outdoor adventurer and travel photographer on a never-ending exploration of her surroundings, both locally and abroad. Her passion for photography drives her to explore unique destinations, capture awe-inspiring views and eternalize epic experiences. She hopes to inspire others to live a life of adventure and curiosity. Featuring a myriad of beautiful destinations, both at home and abroad, Lauren hopes to encourage her followers to get out and explore the world around them. Whether they’re trying to figure out which trail to hike, hotel to stay at, gear to bring along, or clothing to pack, Lauren’s fans turn to her content to find inspiration for living an adventurous lifestyle. You can follow her adventures on Instagram at @splorin.lauren.



Leah Shoup owns the travel website, is a content creator and Spanish translator. She has a knack for finding colorful places wherever she goes (see for yourself on Instagram: @leahshoup) and will never say “no” to gelato while traveling. She currently splits her time between Atlanta, Georgia and Santiago, Chile, but is always looking for the next up-and-coming destination to explore! Her favorite adventures typically involve sunshine, mural hunting and maybe even a piña colada.