Share The Article The first true cold front just blew through my hometown of Louisville, and my mind shot straight to the Caribbean. But I’ve been craving a more ‘off-path’ vacation without the hassle. Trying to map out the perfect off-the-grid Caribbean trip used to end in a huge headache. Historically, if an island was […]
Tag Archives: Caribbean
Travel Guide
10 Most Beautiful Beach Towns Across The Caribbean With Island Charm and Postcard-Worthy Views
11
Oct
Oct
Share The Article I hate seeing what is happening to the Caribbean right now. Every time I fly down, another quiet beach is gone. Some developer paved it over to build a giant concrete resort. You know exactly what that kind of trip looks like. You can do better, I promise. My wife Liz and […]
Travel Guide
5 Of The Safest Popular Caribbean Destinations To Visit This Fall And Winter According To U.S. Authorities
03
Oct
Oct
Share The Article As the temperature starts dropping in the states, the urge to book a flight south becomes impossible to ignore. But with unpredictable weather patterns and shifting global security, choosing the right island requires a bit of strategy. If you want to escape the cold this fall and winter with total peace of […]
Travel Guide
This Undiscovered Caribbean Island With Pink Sand, 85°F Winters, And $15 Local Seafood Dinners Is Breaking Tourism Records
21
Sep
Sep
Share The Article If you think the golden age of discovering an untouched, fiercely authentic Caribbean island is over, think again. As holiday decorations hit the shelves and the damp winter chill settles over the U.S., the urge to escape to the tropics becomes undeniable. When most travelers think of The Bahamas, they immediately picture […]
Travel Guide
This Safe English-Speaking Caribbean Island With Uncrowded Beaches, 84°F Winters, And $5 Rum Punches Is Breaking Tourism Records
20
Sep
Sep
Share The Article When the cabin doors open on the tarmac at Maurice Bishop International Airport, you aren’t hit with the smell of exhaust or generic terminal air—you are hit with the faint, warm scent of sea salt. You step down the metal stairs, look up at the lush island surrounding you and immediately realize […]
Travel Guide
The 5 Safest Undiscovered Caribbean Destinations Where You Can Still Travel Comfortably For Under $100 A Day
16
Sep
Sep
Share The Article Budget-friendly does NOT mean you have to sacrifice on safety, especially in the Caribbean. Way too many people I’ve met think that to stay safe in the tropics you have to pay $500+ a night to stay in a walled-off resort with security. That is so far from the truth, and you’d […]
Travel Guide
This English-Speaking Caribbean Island With 33 White Sand Beaches, 82°F Winters, And $8 Beach BBQ Is Breaking Tourism Records
15
Sep
Sep
Share The Article The second the high-speed boat cuts its engines and pulls into the dock at Blowing Point, the frantic pace of the outside world completely evaporates. You step off the wooden pier, look down at water so clear it looks like liquid glass, and immediately realize you have arrived somewhere genuinely special. There […]
13
Sep
Sep
Share The Article When you spend enough time jumping between Caribbean islands, you quickly realize that the region’s true soul is rarely found inside the guarded gates of a mega-resort. It lives in bustling markets, weathered colonial alleys, and quiet fishing harbors where daily island life unfolds. If you want a vacation that actually feels […]
Travel Guide
5 Best Underrated Towns To Visit In The Caribbean According To Locals and Travel Experts
09
Sep
Sep
Share The Article I’ve spent years traveling around the Caribbean for fun, for travel conferences, and I even lived there long-term twice. When you spend that much time there, you quickly realize there’s a huge difference between a town that looks on great Instagram and a local community that blows your mind in real life. […]
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Sep
Sep
Share The Article Stop defaulting to the same overcrowded resorts where the most strenuous activity of the day is fighting for a pool chair. I know it’s tempting, but travel is sometimes about more than leisure! For decades, the Caribbean has been marketed exclusively as a place to lie on the sand with a frozen […]
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