72 Hours in San Juan, Puerto Rico

There is no better time than now to embrace Puerto Rico’s culturally rich landscape

Photo courtesy of Caribe Hilton
Photo courtesy of Caribe Hilton

For those of us in South Florida, traveling to Puerto Rico might be one of the best vacations around if you’re still hesitant about booking long-distance travel. For starters, the U.S. territory is a mere two-hour flight away on several airlines, including American, JetBlue, Spirit, and Southwest. And let’s not forget you don’t need foreign currency or a passport to enter—even better for those in renewal limbo. Despite the island dropping most travel restrictions surrounding COVID-19 in recent weeks, Puerto Rico is home to the most vaccinated population in the U.S., according to Centers for Disease Control and Prevention, making health concerns far from top of mind.

Old San Juan. Photo courtesy Discover Puerto Rico
Old San Juan. Photo courtesy Discover Puerto Rico

Aside from its relatively safe appeal and power nap-worthy distance from Fort Lauderdale International, PR has continually drawn in crowds from across the globe for its rich cultural scene, ample historical sites, tropical landscape rife with idyllic beaches (we’re talking some of the clearest water), and natural wonders worthy of exploration.

A recent first trip to San Juan, Puerto Rico, left me enamored with the tiny-but-mighty island’s cultural landscape and friendly locals. I’m due back to rent a car and explore more of PR’s hidden gems, but in the meantime, here are some of my picks for what’s worth exploring if you’re booking a quick stay on the northeast side.

Caribe Hilton pool. Photo by Bronwyn Knight
Caribe Hilton pool. Photo by Bronwyn Knight

Stay & Play: While I did a bit of hotel hopping during my week-long adventure, I ended the last leg of the trip at the iconic Caribe Hilton, nestled on a 17-acre peninsula near the Old San Juan historic district—complete with its own secluded beach. This Caribbean landmark has been hosting guests since 1949 and recently undergone a $150 million renovation following the aftermath of Hurricane Maria in 2017. There is much to appreciate (from dining at nine restaurants, playing a round of tennis, and booking multiple treatments at the Zen Spa Océano), but one of the resort’s defining factors is being the inventor of the piña colada, thanks to Ramón “Monchito” Marrero. As an homage to the famed bartender, piña colada­–making demos take place daily at the resort’s Caribar for guests to sample one of the world’s most popular tipples in its natural form. (Try it yourself with the hotel’s recipe below!) You could quite literally plan a vacation at Caribe Hilton and never feel the need to leave, but there is much to see and do on the island. Put on your walking shoes and let’s explore!

El Yunque Rainforest. Photo courtesy Discover Puerto Rico

Adventure Abounds: No matter if you’re staying in the upscale, touristic neighborhood of Condado or farther east in Isla Verde, it’s a must to plan a day to explore Old San Juan (aka “Viejo San Juan” if you want to sound like a local). Walk cobblestone streets lined with OSJ’s notorious pastel-hued houses and discover colorful murals on building facades. You can spend serious time walking historical landmarks like the Castillo San Felipe del Morro, originally designed to defend the Spanish colonial port city from seaborne enemies. OSJ’s architectural allure and hidden haunts beckoned me time and again.

For the more adventurous type, book a tour to El Yunque National Forest, which is less than an hour from San Juan. There are more advanced hiking trails to reach awe-inspiring mountain views and tours for a leisurely experience to discover natural waterfall-fed pools and embrace the glorious scenery. Some of my fondest memories include rope swinging into the lagoon and finding the courage to go down a natural rock water slide at Las Paylas, just on the outskirts of the forest. (It’s seriously such a rush!) There is something special about the tropical landscape—and refreshingly cold waters—that make you feel born again.

Culebra Beach. Photo courtesy Discover Puerto Rico
Culebra Beach. Photo courtesy Discover Puerto Rico

Go Beach Hopping: One of the most obvious reasons to visit PR is to discover some of its most pristine beaches. Depending on who you ask, locals each have a favorite like San Juan’s picturesque El Escabrón beach, ideal for snorkeling, swimming, and catching a beautiful sunset. Do yourself a favor and catch a ferry ride to PR’s crown jewel islands like Culebra and Vieques. White sand beaches and vibrant turquoise waters await for an epic day trip.

Casita Blanca in Santurce. Photo courtesy Discover Puerto Rico
Casita Blanca in Santurce. Photo courtesy Discover Puerto Rico

Culinary Gems: Local vendors and food trucks line up daily in Old San Juan near the waterfront serving up dishes like the tripleta, a sandwich made with ham, sliced or shredded pernil (roast pork), and marinated and pan-seared cube steak. Another favorite in OSJ is La Vergüenza, a chinchorro (casual restaurant) located in the neighborhood La Perla. It boasts a rooftop vibe perfect for people watching and soaking in the local scene while noshing on mofongo and fried fish bites and sipping on the locals’ favorite Medalla beer. For something more sophisticated, don’t miss Santaella in Santurce, serving tapas and creative cocktails in industrial-style digs. Be sure to book your dinner resy ahead of time—tables fill up fast.

Find the Fiesta: Discover why Puerto Rico is known as the rum capital of the world with Flavors Food Tours San Juan. Sample three craft rum drinks on this walking tour while discovering local watering holes. Later, visit La Factoría, where you’ll enter via an unmarked door to find six curated bars, each with its own ambience and drink menu. My favorites included Shing A’Ling, the main dance hall known for playing live salsa, and La Cubanita, one of Old San Juan’s original corner stores-turned-Havana-centric bar. If it’s your first-time visiting San Juan, you’ll want to plan at least one night to discover the neighborhood La Placita. The scene really picks up Thursday-Sunday when lively crowds gather in the street, and PR’s own reggaetonero Bad Bunny can be heard blasting from every bar.

Caribe Hilton’s Original Piña Colada. Photo by Bronwyn Knight_1
Caribe Hilton’s Original Piña Colada. Photo by Bronwyn Knight

Caribe Hilton’s Original Piña Colada Recipe


2 oz. rum

1 oz. coconut cream (Coco Lopez is recommended)

1 oz. heavy cream

6 oz. fresh pineapple juice

½ cup crushed ice


Mix the rum, cream of coconut, heavy cream, and pineapple juice in a blender. Add ice and mix for 15 seconds. Serve in a 12-oz. glass and garnish with fresh pineapple and a cherry.

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