Share The Article I get it. When did booking a simple vacation become work? I have been traveling the world for the last 20 years and have been to over 100 countries, but times are changing, and not necessarily for the better. Did I pay that $24 tourist tax? Do I have something in my […]
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 […]
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 […]
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 […]
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 […]
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 […]
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 […]
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 […]
Share The Article Whenever I talk to people about booking a trip, the very first question they ask is always about safety. Truthfully, the Caribbean is a massive, diverse region. While there are certainly islands where you need to keep your head on a swivel and stay strictly within your resort boundaries, there are others […]
Share The Article Having spent time living in the Caribbean, I learned quickly that the postcard version of the Caribbean often skips over the logistical realities. Safety down here isn’t just about avoiding sketchy neighborhoods; it is about infrastructure, medical capabilities, and how effectively a local government manages the chaos of mass tourism. The U.S. […]