If you've ever fantasized about being washed up on a Caribbean island for a week or two, the Corn Islands off the coast of mainland Nicaragua look like a dreamy postcard come to life. Despite their allure, they're still considered off the beaten path and tick all the boxes for crystalline waters, white-sandy beaches, warm locals, freshly baked coconut bread, and plenty of seafood dinners caught that morning. You'll have the distinct feeling of being in a place like Tulum or Thailand decades ago before the developers arrived and paved paradise.

Charter your megayacht and brush up on your French—we're heading to Saint Barthélemy. Known as St. Barts for short, this stunning nine-mile island east of Puerto Rico is the famed playground for celebrities and no-budget travelers alike. From the plethora of five-star resorts and Michelin-star restaurants to the swanky beach clubs where you can dance on the tables, cocktails in hand, St. Barts is a prized tropical getaway for those with more than a little cash to burn. This celebrity-dotted paradise is well known for its laid-back attitude and French-Caribbean fusion (the Euro is even the official currency), attracting famous jet setters like Jeff Bezos, Jennifer Lopez, Beyonce, Marc Jacobs, Madonna, David Letterman, Heidi Klum, Mike Tyson, Elon Musk, Leonardo DiCaprio, and Paul McCartney.

While the postcard-perfect beaches and teal waters will draw you into Trinidad and Tobago, it's the rich culture and warm locals that will keep you coming back for more. This dual-island nation off the coast of Venezuela is famous for its music scene, mouth-watering cuisine, and an annual festival that rivals Carnival in Rio de Janeiro, Brazil. Spend enough time here, and you won't help but develop a love of fetes (slang for parties) and liming (hanging out with friends). With its colonial past, rebellious spirit, and melting pot of cultures, this Caribbean destination has a cultural heritage unlike anywhere else.