There is a very specific travel nightmare that I actively avoid at all costs: waking up at 6:30 AM on vacation just to play the “towel game” so I can claim a plastic lounge chair at a crowded mega-resort.
When my wife Liz and I are plotting our escapes from our hometown in Louisville, we aren’t looking for sterile all-inclusives or massive buffet lines. We want the authentic, slightly rugged, undeniably gorgeous pockets of the Caribbean where you can actually hear the ocean instead of a booming poolside DJ.
I prefer slinging my Sony camera over my shoulder, lacing up my hiking boots, or throwing on my scuba gear. I want to feel like I’ve discovered something that the massive cruise ships haven’t ruined yet.
If you are willing to embrace a little bit of travel logistics—taking a tiny puddle-jumper flight or catching a local ferry—you can unlock some of the most pristine, crowd-free islands on the planet.
Here are 5 of my absolute favorite underrated Caribbean escapes.
1. Saba
The Vibe: A lush, vertical fairytale in the clouds.
The Ground Experience: I always tell people that Saba’s absolute best feature is actually what it lacks: sandy beaches. Because this striking volcanic peak rises straight out of the ocean without miles of white sand, the massive resort developers completely ignored it.
When you fly in and land on the world’s shortest commercial runway, it really feels like you are landing on the island from Jurassic Park!
Instead, you get immaculate, tiny historic villages connected by a single, dizzying mountain road. As an avid scuba diver, Saba is my personal paradise.
Dropping into the protected marine park to dive the submerged volcanic pinnacles—often without another dive boat in sight—is an incredible, solitary experience. If you want a moody, dramatic, jungle-draped escape, this is it.
2. Dominica
The Vibe: The ultimate rugged eco-adventure.
The Ground Experience: Not to be confused with the Dominican Republic, Dominica is fiercely nicknamed the “Nature Island,” and it demands that you get off the couch.
Liz and I aren’t exactly “sit completely still for seven days” travelers, and I do a lot of rock climbing and hiking, so the intense verticality of this island is a playground.
You spend your days hiking through dense rainforests to find hidden waterfalls or trekking out to the Boiling Lake. (NOTE! If you like to wear gold or silver like me, make sure to leave it behind for this adventure. The sulfur can irreversibly tarnish your jewelry.)
When you need to cool down, you snorkel the Champagne Reef, where underwater volcanic vents create thousands of tiny, warm bubbles that rise around you.
My biggest tip: Leave the flip-flops in your suitcase and pack actual, high-traction hiking boots. You will absolutely need them.
3. Vieques, Puerto Rico
The Vibe: Unpaved, passport-free perfection.
The Ground Experience: There is something incredibly freeing about landing on a tropical island and having to immediately brake your rental Jeep for a herd of wild horses crossing the dirt road. Located just a few miles off the eastern coast of mainland Puerto Rico, Vieques is wonderfully unpolished.
Because much of the land was a former U.S. naval reserve, the shorelines were protected from commercial overdevelopment. You get sweeping, empty beaches completely to yourself.
The absolute must-do: Book a clear-bottom kayak tour through Mosquito Bay. It is the brightest bioluminescent bay on earth. Try to time your trip around a new moon—when it’s pitch black, the glowing blue water looks like pure magic. And the best part? U.S. citizens can fly here without a passport.
4. Bequia, St. Vincent & the Grenadines
The Vibe: Classic, slow-paced yachting culture.
The Ground Experience: Getting to Bequia (pronounced Beck-way) is a bit of a mission, and I am incredibly grateful for that. Because you usually have to fly into St. Vincent and catch a ferry across the channel, the casual, crowd-loving tourists simply don’t bother.
Measuring just seven square miles, Bequia is the quintessential old-school Caribbean hideaway. You won’t find massive cruise ships here, just independent sailors and colorful boutique guesthouses. The move here is to drop your bags, walk down to the totally uncrowded Princess Margaret Beach, crack open a cold local Hairoun beer, and completely decompress.
5. Anegada, British Virgin Islands
The Vibe: A flat coral atoll with the best lobster on earth.
The Ground Experience: Most of the British Virgin Islands are towering and mountainous, but Anegada is a complete geographic anomaly. It is a totally flat coral atoll resting just a few feet above sea level, completely surrounded by a massive horseshoe reef. Because it sits so far out in the BVI chain, it feels entirely secluded.
Pro tip: the local spiny lobster on Anegada is a religious experience. The ultimate itinerary is renting a beat-up motor scooter, riding across the flat island to Loblolly Bay to swim in the electric blue water, and then eating fresh lobster grilled over an open beach fire for dinner.
