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 […]
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 […]
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 […]
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. […]
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 […]
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 […]
Share The Article Whenever I’m stuck in the States for too long, I start dreaming of the Caribbean. But after years in the travel industry, I have realized that not all islands are created equal. Some are essentially just giant, flat sandbars designed for mega-resorts, while others possess a deep, layered culture that makes you […]
Share The Article If you have ever stood on a pier in the Caribbean, you’ve probably witnessed the ultimate vacation nightmare: a massive cruise ship slowly pulling away from the dock while a frantic passenger waves their arms from the shore. It’s brutal to watch. When Liz and I plan our trips, we usually just […]
Share The Article A couple of months ago, Liz and I were standing in the TSA line at SDF in Louisville, holding nothing more than our standard driver’s licenses. If you looked at us, we could have easily been catching a quick domestic hop to Chicago or Atlanta for the weekend. But just a few […]
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 […]