This trip was a surprise birthday present for my boyfriend Leland. We'd been frustrated with our plans to travel to the French island Guadeloupe by infrequent and expensive flights that didn't fit our schedule or budget. After plotting dozens of ways to get from San Juan, Puerto Rico, to Pointe-à-Pitre, Guadeloupe, all of them portentous of travel disaster, I thought, "Why not just stop at San Juan, since it's so easy and cheap to get to?" I have a friend from the island who would be there the weekend before the birthday—things just fell into place. Two days later, the secret plans were made. Two weeks later, we were on a plane.
I had reasoned that with only three days on the island, we would be wise to stay around San Juan. I knew nothing of the island and figured that renting a car would be at least as much of a task as in Europe. (And I doubted the existence of a rail line!) So I booked three nights in a cheap Old San Juan hotel I had found on IgoUgo. The hotel, we discovered on our arrival Friday night, was rather disgusting (more later!), and my Puerto Rican friend booked a room elsewhere for her Saturday evening arrival. She also reserved a rental car for a bit of Sunday driving.
After a few minutes in the car, which we learned had cost about the same as a rental in Tampa (for example), we realized that our plans to remain in San Juan only were a mistake. While the city has some historical neighborhoods, it doesn't have the European (or shall I say un-American?) charm we were expecting. And compared to the natural beauty of the surrounding island, San Juan feels downright drab. Finally, though the nearby mountains reassure you that you haven't landed in Tampa by mistake, the roads and freeways are almost perfect copies of those in the U.S. If you're 25 or older and can drive, there's little reason not to rent a car.
We added my name to the car rental and cancelled our remaining nights at the dumpy hotel. Liberated, we embarked on a trip first to the rain forest, then the beach, and eventually circled the whole island. The beaches, which are gorgeous, are practically deserted in winter months. Don't worry, though; it's plenty warm enough (80ºF on our trip) to sunbathe and swim.
Culturally, things continued to feel pretty American wherever we went. Spanish? Sure, just like the Bronx. With a few exceptions, most people we came across spoke to us in good English or bad English, and ignored our attempts at Spanish. Lest we sound too naive, I should say that we've visited Madrid, Barcelona, and San Sebastian (all in Spain) and spoken nothing but Spanish there. But unless your Spanish is tip-top (and, ideally, you look it), don't expect too much practice time on this island.
When we flew out Monday evening, we felt like we'd been in Puerto Rico for much longer than three days. We saw lots, spent little, and got a mild sunburn. If you're looking for a three-day winter escape and you live near a big East Coast city, book a flight (and a car) for San Juan.