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 …
Every time my wife Liz and I lock our front door, give our golden retriever Lemon one last goodbye pat, and head to the airport for a Caribbean escape, the goal is always the same: find a place that feels wildly authentic. If you are exhausted by the massively paved, flat, all-inclusive beach traps that …
Safe. Uncrowded. Affordable. Finding all three in the modern Caribbean usually feels impossible. But if you are willing to bypass the major tourist hubs and trade the mega-resorts for a tiny commuter flight, there are three breathtaking, untouched islands still hiding in plain sight. It is getting incredibly hard to find islands that haven’t been …
It is official: the golden era of low-bureaucracy travel, where you could simply grab your passport, throw some swimsuits in a carry-on bag, and board a flight for a tropical getaway, is rapidly coming to an end. Across the globe, incredible destinations are completely tightening up their borders and introducing brand new digital hoops for …
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 getaway, only to …
Who says travel has to be expensive? Well, lots of people actually, especially as airfare has reportedly shot through the roof, shuttering Spirit Airlines and driving fares higher for those still taking to the skies. Fortunately for you, we’ve found some of the best deals happening this summer so you don’t have to skip your …
Whenever I’m back home mapping my next trip, my inbox is constantly flooded with the exact same question from travelers: “Where can I go in the Caribbean that is actually safe, totally uncrowded, and doesn’t feel like a giant tourist trap?” It is getting increasingly difficult to answer. Mega-resorts are expanding rapidly, and finding an …
When I am mapping out a Caribbean getaway, my absolute biggest nightmare is ending up on a beach where I have to fight 500 cruise ship passengers just to secure a plastic lounge chair. For decades, the islands have been building massive mega-resorts and giant deep-water ports to pack in as many tourists as humanly …
Trying to map out the perfect off-the-grid Caribbean trip used to end in a massive headache. Historically, if an island was actually safe and totally undiscovered, getting there involved a brutal itinerary… we’re talking multiple layovers, terrifying tiny commuter planes, or sketchy ferry rides. On the flip side, the islands with easy, direct flights from …