Old San Juan, Puerto Rico
Second in size to only Santo Domingo, San Juan is a big Caribbean city. From the moment your foot touches Puerto Rico's rich, fertile soil, its scale becomes apparent. Three-lane highways surround San Juan's city limits, meandering streets fill dense districts within. Amongst the most popular quarters are Condado, Isla Verde and Old San Juan.
The southern half of Old San Juan is distinctly more commercial. The cruise ships land in this part of town. If you start in the southern half of the city, head north on the west side. Following this route, you will pass landmark sites including Pigeon Park, La Fortaleza and Cathedral San Juan Bautista. Take a moment to catch your breath at Pigeon Park (a.k.a. Parque de las Palomas). The views over the south side of the city are pretty and Capilla del Cristo, which sits right at the park's entrance, is an architectural marvel.
When you emerge on Old San Juan's far northern side, you will know. All cobblestone roads and rustic buildings with colorful, wooden doors, this part of Old San Juan is perhaps the most charming of all. Home to two attractions integral to San Juan's history, this area lives and breathes Puerto Rican tradition and values. Straddled by Castillo de San Cristóbal and San Felipe del Morro Fort, the northern half of Old San Juan is one part of the city that can't be missed.
History lives here, and the setting is most majestic. Open to the wild Atlantic Ocean and the beach community La Perla, stand here at sunset and watch the waves roll and the surfers come in. While the sky glows and the day fades, behind you, the rest of Old San Juan buzzes and comes alive.
Within the streets that are set back from the promontory that overlooks the ocean and the forts, you will find a warm, local community. Between restored buildings, there are still many that have not been touched up, lending a certain authentic feel to the streets. Walk through these northern parts on a Sunday and catch a local band playing for city dwellers.
Lined with bars and tapas lounges, and peppered with high-end restaurants and charming hotels, there are plenty of cozy nooks and crannies to tuck into on the north side. And, almost everywhere you go you're reminded of the history that makes this spot to special. Even sitting table-side in St. Germain's tapas lounge, there's markings showing that historic figures lived in this building. Downplayed, it all feels real.
Puerto Rico, you sure do it better!