Share The Article I’ve spent years living in and traveling around the Caribbean. I’ve covered tourism conferences like CHTA, sat down with tourism boards, and made lifelong friends from island to island. When you spend that much time on the ground, you quickly realize there’s a huge difference between a beach that looks great in […]
Tag Archives: Caribbean
01
Aug
Aug
Share The Article There is a growing epidemic in the travel world right now: algorithm fatigue. You see a stunning, secluded beach on your social feed, book a flight, and arrive only to find three cruise ships docked in the bay and a two-hour wait for a mediocre lunch. When I am plotting my next […]
Travel Guide
The World’s Safest Country To Visit In 2026 Is A Caribbean Beauty With Year-Round Perfect Weather And Stunning Turquoise Waters
26
Jul
Jul
Share The Article There is a specific, sinking feeling you get when you have to constantly check your pockets in a crowded tourist trap or nervously navigate dimly lit streets trying to find your hotel. When my wife Liz and I are plotting our escapes from the unpredictable weather in Louisville, we want to trade […]
Travel Guide
Americans Can Now Fly Nonstop To This Caribbean Paradise For The First Time Ever From These 3 Cities
20
Jul
Jul
Share The Article Sure, everyone knows the Bahamas, Aruba, and Jamaica, but not everyone has discovered the unspoiled vibe of one of the absolute best destinations in the Caribbean. While the classic hotspots are currently dealing with overcrowded beaches and massive mega-resorts, there is one tropical haven that has managed to keep its pristine, upscale […]
05
Jul
Jul
Share The Article As someone who spends half the year living out of a suitcase and the other half obsessing over our next trip, I get this question constantly: “Where can I splurge on a Caribbean vacation without feeling trapped on the resort property?” There is nothing worse than dropping five figures on a luxury […]
31
May
May
Share The Article Planning a summer beach trip shouldn’t give you gray hair. When you finally get the time off work to pack a suitcase, the only thing you want to worry about is whether you packed enough sunscreen. You want to sip a cold drink in the sun, not stress out about walking back […]
29
May
May
Share The Article It seems everyone’s got their eyes set on an Italian or Greek island summer this year, but you know what we’ve always said: when those turquoise-water and piña colada cravings hit, there’s nowhere better to switch off and kick it back than the good ol’ Caribbean. Now, we get it if you […]
Travel Guide
Aruba Was Just Voted The Safest Destination In The Caribbean: Here’s Why It’s My Go-To Escape
25
May
May
Share The Article When you travel as much as I do, peace of mind stops being a nice-to-have and starts being the whole deciding factor. We all want the crystal-clear water and the white-sand beaches. But do you actually want to relax, or do you want to spend a week with one eye open? Because […]
30
Mar
Mar
Share The Article I spend a massive chunk of my year flying around the Caribbean, and I’ve noticed a huge shift in what travelers are actually looking for right now. For decades, the standard playbook for a tropical vacation was to book a flight, shuttle to a massive, walled-off all-inclusive mega-resort, and never leave the […]
28
Mar
Mar
Share The Article In this day and age of information overload, it’s a tall task to find true off-path destinations. When it comes to the Caribbean and South America, there are only so many left to unveil, but one better known for its dreamscape rainforests over its coastline isn’t trying to become the next big […]