I never planned to live in Puerto Rico. Not when I was growing up, not when I was building my business, and not even when I sold it. But just after that, a dear old friend of mine told me he’d seen a video about Puerto Rico and not only did it seem breathtakingly beautiful, it was also one of the great tax havens on the planet for Americans. I moved there a week later, and I haven’t regretted it one bit.
I checked into the Condado Vanderbilt with the idea of staying there until I found a permanent place to live. The service is impeccable. I would give it a sixth star if I could. It was built in 1919 by yes, the Vanderbilt family. Grandson of family founder Cornelius Vanderbilt, Frederick William Vanderbilt to be exact. He hired the same architects who designed Grand Central Station in Manhattan. No expense was spared. No detail too small. And over time, the hotel has been magnificently restored and maintained. I still go there quite often. It is one of the first places I bring friends to help them reset their expectations of the US territory. And we still hold all of our Trunk Shows there when we are on the island.
While the Vanderbilt has a classy and elegant timelessness, it is also home to the absolute best Latin food beach bar in San Juan; maybe on the whole island. I blame the twenty pounds I’ve gained since my move, squarely on the fried tostones and empanadilla
s I fell in love with here. (Truth be told, it could also have been the Mojitos). Regardless, they are indulgent and excellent. I’ll be ringing in the New Year there on water because they throw the best party around. I will be decked out in elegant velvet and tartan plaid and can’t wait to be the best-dressed guy there. Again.
When I wasn’t eating fried something or other over the course of that first month, I was exploring the island and every day was more eye opening than the last. I have never seen so much geographic diversity in such a small place. It’s about 100 miles across, and on the West coast there is jungle, on the East, a desert with cacti and appropriate critters. In between the two, there are rivers, caves, beaches and coves to explore. Zip-lining. Surfing. Even hang-gliding are all available and popular. I haven’t done them all, but I’m checking them off one by one. I have spent a good deal of time in the town of Esperanza on Vieques, an island off the east coast of Puerto Rico’s mainland. It is a bohemian playground for backpackers, dune buggy enthusiasts and those who admire wild horses, which are everywhere, including on the beach.
I think though, that with everything there is to do in Puerto Rico, my favorite thing is pretty simple. Put on a pair of shorts and a white linen shirt. Pour a double shot of Zacapa 23 rum in a highball. Then walk down to the city square, the fort, or the harbor-front around sunset with one of my favorite cigars, say a Partagas Lusitania or a Nat Sherman Sterling, or if I’m really feeling good, a Cohiba Behike. It’s relaxing. And beautiful. And a long, long way from Indiana in more ways than I could ever explain.