Old San Juan is my favorite destination in Puerto Rico. The history, tropical pastel hues, colonial architecture and incredible cultural offerings are simply incomparable, not just in Puerto Rico but most of the region. And it's all the more remarkable considering how small this city is, just seven square blocks partially encircled by an ancient wall. I've lost count of the number of times I've been here, but every time I go back, I experience yet another small sense of wonder.
Sightseeing, dining, nightlife, culture... it's all at your fingertips here. And to enjoy it to the fullest, I'm going to give you a few tips on what not to do when you visit Old San Juan.
Anyone who has been to Old San Juan will agree with me on this one. Actually, anyone who has ever rented a car in Puerto Rico might be nodding their heads. There are many ways to get around the island, but while you're within the confines of Old San Juan, I recommend you leave the car at your hotel. For one, there is a free trolley that shuttles passengers to every major site. For another, the roads are narrow, and parallel parking will be an adventure for all but the most seasoned parallel parkers (I speak from experience).
And finally, traffic can be brutal. And finally, this city is best experienced on foot. And if you do need wheels, you'll find taxis at the central Plaza de Armas, near Plaza Colón, and at the pier by the Sheraton Old San Juan.
Now, the one exception to this rule is if you want to rent a car to get out of Old San Juan and explore the rest of Puerto Rico. In that case, a car is your friend. Just not while you're in the city.
Don't Wear Heels
Ladies, this is an important corollary to point #1 above. Comfortable shoes are a requirement to enjoy this city. If you don't believe me, try making the uphill trek from Castillo San Cristobál to El Morro in heels. I can't imagine it would be a fun trip.
And then there are the adoquines, those beautiful blue-tinged cobblestone streets. I imagine they must be like negotiating a minefield for anyone in heels.
El Jibarito, The Parrot Club, Dragonfly and so many other eateries in the old city, your taste buds will thank me.
Don't Stay Indoors
There are some hotels in Old San Juan that will invite you to stay right where you are. Whether it's the boutique comforts of Chateau Cervantes, the historic beauty of El Convento or the casino at the Sheraton (the only one in Old San Juan), you may be tempted to linger indoors. Many of the old city's hotels have a unique charm and capture the essence of the city.
But you do yourself an injustice if you don't spend as much time as you can out and about. The museums, monuments, plazas, promenades, cafes, and shops await. Even a walking tour like mine will keep you outdoors all day.
Dont Go Swimming
This one might surprise those of you who aren't familiar with Old San Juan, but it doesn't have a beach. At least, nothing like these stunning beaches of Puerto Rico. If you must get into the water while you're in the old city, your best bet is to walk along the Paseo del Morro, where the water is calm beyond the San Juan Gate. But honestly, you're much better served to take a taxi or renting a car to get out and explore the shores beyond Old San Juan.