Go to Puerto Rico to surf.
When I came to the realization that I was missing out on amazing surf, I caught a cab back to the airport to rent a car. Through a series of "unfortunate mistakes" on their part, I ended up with 2014 Jeep Wrangler - at the economy price. They insisted on cleaning the Jeep from top to bottom, not matter how many times I explained that I would be getting it absolutely filthy. I drove off in my shiny white Wrangler and picked up a longboard at the local surf shop down the road.
There was an incoming swell over the next 3 days, and I was stoked to have the transportation and board to enjoy it. Straight from the surf shop, I drove down to a spot called Wilderness. The road to get there is pretty rugged, but I saw plenty of small sedans and compact cars make the round trip. When I say road, I really mean a dirt and sand road with massive holes littered throughout. Although I would have made the trip regardless, having the Jeep made it much more enjoyable and stress free. I spent the rest of the day at Wilderness, occasionally breaking to grab some more water and apply more sunscreen.
The surf report for the next day was mixed. Depending on where you were on the island, the swell direction and wind direction was either going to make it small and fun, or slightly less small and more fun. I wanted to get in the water by sunrise, and Sarah (the hostel owner agreed to come with me). The morning of she changed her mind and I ended up going alone. I couldn't blame her - it was about 5:30am and the report said 2-3ft. Not worth getting up that early.
When I pulled up, it was glassy and 5ft, consistently. There were a few other older guys in the parking long, but not a soul in the water yet. It was about 6:10 am. The guys in the parking lot were busy putting their leashes on, waxing their boards, and putting on wetsuit tops. Yes, you read that correctly, wetsuit tops.
What I learned very quickly was that Puerto Ricans (locals and transplants) were very, very spoiled. They don't know what cold water is. It was 6:10am, the sun wasn't up yet, and the air temperature was already 82*F. The water temperature was about the same.
So of course, as my pasty white self walked towards the water with no wetsuit top, the guys began to all give me sideways looks. One of the guys was nice enough to ask me where I was from, and if I knew where to paddle out. These guys were old, and proud of it. They made a point of telling me that they were the first guys to surf in Vietnam, and frankly I think they were shocked to see a young-gun like me with a longboard.
We all paddled out together, and it turns out most of them were from New York. A few of the guys were born in Puerto Rico, moved to Long Island NY, and then moved back to Puerto Rico. They all ended up being incredibly friendly and hospitable, and they loved sharing their spot with me.
10 hours later, when I returned to the hostel, all I could tell Sarah was, "boy, you really missed it."