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 influencer at My Darling Passport, where she covers colorful adventures, feminie escapes and bucketlist destinations. Caitlin started My Darling Passport as a way to share her passion for traveling to faraway lands and inspire other 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 Caitlin’s adventures on My Darling Passport and on Instagram at @MyDarlingPassport.

Beachtastic Facts:

How many times have you traveled to the Caribbean? So many times! Definitely over 20!

What is your favorite Caribbean locale? This is such a hard question, but if I had to pick one, I’d say St. John in the USVI.

How many years have you been covering travel? I’ve been passionate about travel my whole life and have been covering the industry for the past three years.


Hannah Rheaume is a travel blogger at The Sunny Side of Things. She has been traveling full time since leaving the comforts of her full time public relations job in November 2016. Hannah highlights topics such as luxury adventure, destinations and lifestyle. She loves discovering off the beaten path places like Malta to the faraway lands of Chiang Mai, Thailand to the skyscrapers of Hong Kong and the beaches of Australia. Hannah is always on the hunt for discovering new perspectives all over the world, as seen here. When she is not traveling she calls Maine home.

Beachtastic Facts:

How many times have you traveled to the Caribbean? Not enough! 2 times.

What is your favorite Caribbean locale? I’ve always disliked this question. Every destination is so unique! I loved Havana but I also really loved exploring the islands of Puerto Rico.

How many years have you been covering travel? Going on 3 years now!


Kana Imamura is an established Travel Instagrammer & Blogger at Life in Wanderlust from sunny Los Angeles, California. After 8 years as a director in corporate hospitality and earning her master’s degree in Hospitality Management, she closed her office doors to travel in 2015. Following her love for photography and writing, she quickly gained followers and readers from all over the world and now has almost 100k in social reach. Kana currently balances travel photography & writing, advising new Travel Bloggers and running her consulting company for hospitality & restaurant businesses. Follow her adventures on Instagram: @lifeinwanderlust_ and blog:

Beachtastic Facts:

How many times have you traveled to the Caribbean? 5 times.

What is your favorite Caribbean locale? Bahamas (Nassau) and the Cayman Islands!

How many years have you been covering travel?  3.5 years as a blogger and Instagrammer and over 10 years in the travel industry!


Natalie Anastasia is a travel and lifestyle blogger based in San Francisco, California. On her blog, Pastels & Passports, she writes about all of her adventures in San Francisco, as well her domestic and international travels. In her travels, she consistently tries to find those particularly hidden gems. Her favorite and most memorable travel experiences have always been the super unique and hyper-local one. For instance, getting a fish pedicure in Venice or staying at a hotel on the edge of the earth. She says travel is important to her because it keeps her curious, energized and passionate. You can follow her on Instagram at @PastelsandPassports.

Beachtastic Facts:

How many times have you traveled to the Caribbean? I’ve traveled to the Caribbean somewhere between 10-15 times! I have been fortunate enough to explore many differnt Caribbean islands.

What is your favorite Caribbean locale? Gosh! Each island is so special and unique, but my favorite would have to be Turks & Caicos for nostalgic reasons.

How many years have you been covering travel?  I have been covering travel on my blog since the fall of 2016 when I moved across the country from Florida to San Francisco.