Old San Juan

Old San Juan offers historically and culturally significant experiences including a walk through 500-year-old forts, visits to UNESCO sites, historic churches, museums, the second oldest cathedral in the Americas and Ponce de Leon’s mansion. Cobblestone streets and pastel buildings are perfect for exploration during the day and variety of restaurants and shops make for a complementary evening.

Old San Juan is much like the villas of of other Spanish Caribbean islands/ lands but there is a local peace to Old San Juan that makes it special. High and low end vendors, colorful buildings, stray cats hanging out and music playing from the restaurants through out the area make it a place to spend a long afternoon of eating, walking and taking it all in.

RENDEZVOUS. A great hangout! I love the streets of Old San Juan, there is something magical about the history, the architecture, the music, the culture! I just love to get lost, there is something different on every street.

Old San Juan has a decadent color palette straight from Willy Wonka. The Spanish architecture of its seven-square-block enclave dates back hundreds of years. Conflicts, invasions, and natural disasters have not kept this city down, and it is often referred to as NYC’s Second City. No trip to Puerto Rico is complete without a stroll through Old San Juan.

My wife and I visited Puerto Rico in October of 2010. The first place we visited was Old San Juan. The fortress of El Morro is not to be missed. You could literally spend a half day there alone. The rest of Old San Juan is full of historic buildings, cobblestone streets, street vendors offering arts and crafts, and great restaurants. We spent a full day in Old San Juan and enjoyed just walking around taking in the sights, shopping, and eating at a Cuban-style restaurant . An arts and crafts fair near the cruise ship docks had great offerings.

At Pr Tea Co. in Old San Juan, you can sip 100 percent Arabica coffees, healthy looseleaf teas, and the most innovative product, CafTea. CafTea brings together the health benefits of high-quality tea with the energy boost of coffee for a delicious hot beverage. No artificial ingredients are added, and the drink actually contains 33 percent less caffeine than regular coffee—for a boost without the jitters. Ask the manager to tour the small production space in the shop and take in live entertainment while you sip. Additionally, each cup of CafTea comes with a whimsical design drawn into the foam. Some flavors to sample include French Vanilla Bean, Toffee Hazelnut, Coconut Truffle, and Coconut Chai.

If you’ve had enough of the tropical beaches and feel the need for a bit of a cultural city experience, Old San Juan is a drivable day trip or overnight stay, about two hours east of the popular surf town of Rincon. The colorful streets and architecture, along with the history of the city, make this a worthwhile visit. With everything in close proximity, feel free to walk up and down each street. EAT AND DRINK Stop in the home of the very first piña colada at Barrachina restaurant and sample classic Puerto Rican food. Afterward, walk down to play a round of pool and add your name to the graffiti walls of El Batey bar. For a sample of gourmet Mexican fare, La Madre is a must. Order a side of elote corn and sample one of the incredible margaritas made with fresh fruits. You can’t go wrong with anything on the menu. STAY A great go-to for a reasonable price and perfect location while offering a true feel of Old San Juan is Da House. It’s a quaint four-story building with an art gallery in the lobby, communal areas with Wi-Fi, and a rooftop view. SHOP With shops on each corner, simply explore the streets. Calle Fortuleza and Calle San Francisco are a few main drags. Stop in the local cigar and hat shops and find familiar favorites like Coach and Louis Vuitton. SEE Tour the 16th-century fort Castillo San Felipe del Morro. The old lookout towers have one of the best views of the ocean by far.

If you’re looking for a place to visit that seems to blend perfectly, parts of Europe, the Caribbean, Africa and the Americas, look no further than Old San Juan. The people are incredibly engaging and warm, and the city, visually stunning. It seems to ooze it’s rich history between each of the street’s cobblestone blocks. Explore the intimate streets and take in the amazing vistas from high atop the fortress walls of the centuries old Castillo de San Cristobal and del Morro. Think high Pacific coastline or possibly Madeira, with that wonderful azure hue of the surrounding sea that is, the Caribbean. There are a ton of amazing places to stay, dine and drink, and the city has a youthful vigor that felt contagious. And, the fact that Puerto Rico is a U.S. territory wasn’t overtly noticeable.. or even vaguely so, with perhaps the exception of the plentiful English that is spoken by nearly everyone. Take in the El Yunque rainforest, Luquillo beach and the food/vendor kiosks that border this beach area, all a short drive from San Juan. Oh, and I’m going back.. that’s for certain.

The streets of Old San Juan are filled with beautiful vibrancy

Vibrant, candy-colored buildings set against sunny, bright blue skies and outlined by the sparkling sea; walking through Old San Juan feels as if you’re in a make-believe city. You can easily spend a day wandering the narrow streets, which are filled with cafes, restaurants, boutiques, and touristy shops. The city sits on a hill, and making the hike up to the top is definitely worth it. I spent a full day in the city walking up and down every street, taking in all of the life, color, character, and architectural details of the city.

Still a high school student at the time, I was thrilled when my cousins invited me to spend a night out on the town in San Juan. After a few rounds of tequila, an adventurous friend invested $75 in an oversized box of fireworks. We found a deserted alley just outside of the city center, and took turns setting off the fireworks and keeping an eye out for anyone who might discourage our antics. It wasn’t until my family was selected for additional screening at the airport that I realized the consequences!

Ben and Jerry’s in Old San Juan

Wandering through Old San Juan, I found this spooky figure hanging from a balcony overlooking La Perla and its ancient, beautiful cemetery. It was Halloween, or “Dia de Brujas” in Spanish, and this decoration portended the wildest Halloween night I’ve ever celebrated in my life.