I’ve long said that my favorite authentic island experience to date has been the small island of Lanai, which some may be surprised is actually a Hawaiian island, just off the coast of Maui. With no stoplights, only a couple franchises, and many more miles of unpaved roads than paved roads, Lanai was a welcome experience for this off-the-beaten-path traveler. However, it now moves into my favorite authentic island experience in America, as its rank worldwide has now been supplanted by most recent island experience, Cayman Brac, one of the sister islands of Grand Cayman.

Though familiar with the Caribbean, I didn’t even know that Cayman Brac was a destination until I was invited to be hosted by the Cayman Islands. And that term, “destination,” may be subjective being there’s only one hotel on the entire island, which can be driven from one end to the other in 30 minutes. There are no stoplights, no franchises, no high-rises, and no nightlife. But it’s for these reasons that it is a destination. Most of the island is undeveloped since a bluff covers a majority of it. Local food menus change daily based on local seafood availability. And yet the waters around it are considered some of the best diving waters in the world according to the Cousteau family (and many others). But while you can read more about its food, history, and culture in my article for Travel Mindset, below I feature some of my favorite photos from my recent trip to Cayman Brac.

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I grew up in North Carolina, lived in South Carolina, spent a season in Costa Rica and South Africa, traveled all around Europe, and have called Seattle, San Francisco, and now Los Angeles, home, yet there’s one place that I get more questions and requests about: Big Sur. And it’s for good reason, due in part because of the place it holds among the best drives in the world, but also because I talk about it so much. I believe every traveler wants to see the world, but I also believe that there are one or two destinations that every traveler gravitates toward more than others. One of those places for me is Central California, and more specifically, Big Sur.

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How many countries have you been to? That’s the question I’m most frequently asked. When I lived in the south I was repeatedly asked who my family was (or when I was getting married or having kids). When I moved out to the west coast I was asked what I did for a living. And now when I tell people what I do, I’ve been increasingly asked how many countries I’ve been to. All of these questions, however, seem to be a question of status. I live amidst a generation that is the first to have the accessibility it does to travel. A person with the desire and means could travel to every single country if they wanted to. And people have, like author Chris Guillebeau, who recently visited every single country (193) in the world, using frequent flyer miles and RTW tickets to travel to more than 25 countries per year before reaching his goal. And what a milestone. It wasn’t long ago that it was simply impossible to visit every country in the world. Now that’s possible.

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