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 want to explore …

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 try to fly …

There’s a trap with the standard tropical vacation. You spend months looking forward to it, you fly down, and you spend five days straight doing absolutely nothing but sunning, drinking cocktails, and eating heavy buffet food. By the time you get back home, you feel exhausted—you basically need a vacation to recover from your vacation. …

When most people start mapping out a Caribbean getaway, their minds immediately default to the massive, heavily marketed heavyweights. They look at sprawling mega-resorts in Jamaica or fight for a sliver of sand in the Bahamas. But if you want to skip the intense crowds and find an island with actual soul, raw jungle beauty, …

Right now, when I open my social media feeds for inspiration, all I see is a continuous, exhausting loop of people fighting for a six-inch patch of pebble beach in Positano, or waiting in a two-hour line for a mediocre $30 spritz in Santorini. The Mediterranean is undoubtedly beautiful, but the summer crowds have turned …

The first time I visited Playa del Carmen, I was absolutely hyped to finally check out the world-famous Mexican Caribbean beaches. But when I walked down to the water, the sand was totally covered in massive, rotting piles of sargassum seaweed. The smell was intense, the water was dark brown, and it completely ruined the …

There is a huge difference between just visiting the Caribbean and actually seeing it. I was recently down in St. Lucia with my wife Liz, vacationing and working on a travel feature (they’re one and the same in my line of work). Instead of cramming into a standard air-conditioned taxi at the airport, we decided …

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 hours later, the …

There is a universal travel nightmare that Liz and I face every single time we pack for a Caribbean getaway out of Louisville. It’s that frantic, twenty-minute scramble where we tear the house apart looking for our passports while our golden retriever, Lemon, watches us in utter confusion. Usually I’ve left it in the last …

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 escape, I am …

Every time my wife and I are packing for a Caribbean escape, there is always that frantic ten-minute scramble where we tear the house apart looking for our passports. It is the universal headache of international travel. But there is a massive travel loophole that completely eliminates that stress, and it’s about to get a …

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 …