Why did you choose this adventure?
Cuba has a mystique unlike anywhere else on the planet. I’d always read and been told that going to Cuba was like stepping back in time to a place where people still rode by horse and buggy or drove classic 60-year-old cars, and socialist propaganda billboards stood in place of commercial ads. With the implications of a thawing U.S.-Cuba relationship, I wanted to see it before it started catching up to the 21st century.
Packing Essentials: What did you use most?
Lightweight, breathable clothing. Light wool tanks, a synthetic long-sleeve shirt, and boardshorts are great multi-purpose staples. If you pick the right colors/patterns, they’ll also help conceal sweat.
A good daypack. Suitable for any daily adventure to house the essentials. Don’t forget sunscreen.
Reusable water bottle and SteriPEN. I’m a big fan of being able to make any water safe to drink. It’s convenient, cost-effective, and good for the planet.
What were your trip highlights?
Hiking to pristine waterfalls and pools in the lush hills outside of Trinidad. Horseback riding through yucca, tobacco, and sugarcane farms along the striking limestone monoliths of Viñales. Wandering the vibrant streets of magical Havana, with its crumbling elegance and steady pour of live music. Scuba diving near the Bay of Pigs, with its warm water, amazing clarity, and pristine reef teeming with colorful sea life. Plus, it’s uncannily affordable, with a 2‑hour session only running you $40 per person.
What makes this place special?
What makes Cuba special is its timeless antiquity, the diverse beauty of its terrain, the fascinating mix of Latin and African culture with former Soviet influence, and the indomitable strength and spirit of the Cuban people. To say they’ve endured a lot is an understatement, and they’re still incredibly warm, generous, and always looking to crack a joke.
What was the craziest thing that you saw?
On the drive from Trinidad back to Havana, I saw an old man riding a bicycle while holding the reigns of a trotting horse, all on the side of a six-lane highway.
Where do you want to go next?