by Matthew Allison | Mar 15, 2026 | Caribbean
Puerto Rico: The Island That Was Missing After visiting every independent country in the Caribbean and numerous other unique islands, I felt like I couldn’t say my journey in the Caribbean was complete without visiting one of its largest islands — the U.S. territory...
by Matthew Allison | Nov 29, 2025 | Caribbean
November 2025: Thanksgiving on the Pirate Island of Tobago Why We Chose Tobago With a free week over Thanksgiving, Paula, Indie, and I decided to spend the holiday on a Caribbean island I’d been wanting to visit for years. My first trip to Trinidad—where I watched...
by Matthew Allison | Jul 26, 2025 | Caribbean, North America
From Timbuktu to Bermuda July 2025: Over the past year, I was fortunate enough to visit two locations with legendary names that I had always heard of, but never truly imagined I would visit. These are places that, for many, almost seem fictional and are often believed...
by Matthew Allison | Jan 26, 2025 | Caribbean, North America, Default
New Year’s in Cuba: A Journey Back in Time December 2024: Cuba has long been one of my favorite countries in the Americas. Despite enduring over 60 years of communism and crushing sanctions, its people remain kind, resilient, and full of life. There’s a timeless...
by Matthew Allison | Feb 22, 2024 | Caribbean, North America
February 2024: For years, I envisioned this exact moment—visiting my final United Nations-recognized country, completing my journey to all of the world’s 197 countries. I wanted this special milestone to coincide with my six-month-old daughter Indie’s very first...
by Matthew Allison | Feb 18, 2024 | Caribbean, North America
February 2024: On this two-week, five-country journey to visit my final five sovereign nations, my nephew, friend Jimmie, and I found ourselves in Saint Vincent and the Grenadines—a place that felt less touristy than the other islands we visited. Our main goal here...
