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 […]
Share The Article Planning a Caribbean trip seems foolproof. You book a flight, throw swim trunks in a bag, and assume the rest will work itself out. It won’t. Liz and I have spent a big chunk of our lives in the Caribbean. We’ve made every rookie mistake in the book. We’ve been stranded without […]
Share The Article As the motorized water taxi glided to a halt and I stepped out onto the white sand, the noise and stress of the modern world disappeared. I looked out over a horizon dotted with tiny palm-fringed islands, and realized I’d found a completely untouched corner of the Caribbean. There are no mega-resort […]
Share The Article Most Caribbean marketing is purely fantasy. The brochures show you empty sand and local culture. You book the ticket, step off the plane, and get dropped off at a mega-resort with two thousand other people. Is that travel? While you’re technically in a new place, it doesn’t feel authentic. If you want […]
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 […]
Share The Article When the winter freeze kicks in, every travel publication on the internet starts pushing the same tropical destinations. But we aren’t just any travel publication. Travel experts are sounding the alarm on Caribbean overcrowding this season. No worries, we’ve got you. One of my main missions as the Editor here at Travel […]
Share The Article When winter rolls around, most travelers stick to a predictable formula. Millions of winter-weary travelers fly to the same handful of commercialized island hubs. You spend weeks dreaming about a relaxing tropical escape only to drop thousands of dollars to stand in a buffet line, fight for a pool chair at 7:00 […]
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 […]
Share The Article Finding a Caribbean island escape that doesn’t drain your bank account usually feels like a lost cause. When you factor in flights, hotels, and food, a simple long weekend can easily push into the thousands. But you do not have to settle for staying home this season. Travel experts at Kayak recently […]
Share The Article As the travel world moves its focus toward 2027, major publications are dropping their highly anticipated destination lists (keep an eye out for ours soon!). Lonely Planet just released their Best in Travel 2027 lineup this week, and they highlighted some incredible spots across Latin America and the Caribbean. They gave shoutouts […]