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 […]
Tag Archives: Caribbean
Travel Guide
This Caribbean Island Is the ‘Little England of the Tropics’—With a UNESCO Downtown, a Historic Steam Train, and Rugged Atlantic Views
21
Aug
Aug
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 […]
20
Aug
Aug
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 […]
Travel Guide
These Are The Top 5 Caribbean Beaches Americans Can Visit Without A Passport, From Puerto Rico To The Virgin Islands
04
Aug
Aug
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 […]
30
Jul
Jul
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 […]
10
Jul
Jul
Share The Article The U.S. State Department has just rolled out a major security update for American travelers heading down to the Caribbean this season, and it is something you absolutely need to pay attention to if you have a tropical vacation on the calendar. When you are busy packing your bags and counting down […]
05
Jun
Jun
Virgin Voyages has revealed an exciting new programme of 38 Caribbean sailings aboard the Resilient Lady for 2028. These voyages, now available for booking, will operate from Miami between May and October, focusing on four and five-night itineraries. Destinations include Key West, Grand Turk, Grand Cayman, and Puerto Plata, alongside the exclusive Beach Club at […]
02
May
May
Puerto Rico is a territory of the United States in the northeastern Caribbean Sea. The island of Puerto Rico is famous for its … source
28
Apr
Apr
Share The Article Planning a Caribbean escape in 2026 feels a lot different than it did just a few years ago. Even the island I used to live on has recently gone from Level 1 to Level 2. While we’re all chasing that perfect turquoise horizon, the reality is that the “safety” of an island […]
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