Open Road

Finding Mother-Daughter Compromise in San Juan, Puerto Rico

While I wanted to see the parts of San Juan that weren’t in the guidebooks, my mom was looking for a luxurious respite.

By Marianella Orlando May 25, 2017 Published in the June 2017 issue of Houstonia Magazine

"I think we’re in the ghetto,” my mother said as we attempted to navigate our rental car from the airport to our hotel in San Juan, Puerto Rico. We were surrounded by barren bodegas, ramshackle cars, and run-down homes, covered in graffiti and boarded up with wood. The setting, to Mom, was far from ideal. Yet I felt like jumping out to wander the streets, camera in hand.

When I was growing up, my curiosity always worried my mother. Even to this day, she warns friends and family, “Keep an eye on her. If she sees a dark hole somewhere, she’ll find her way into it.”

It wasn’t long before we emerged from our bleak surrounds into Condado, an affluent San Juan neighborhood filled with upscale beachfront resorts, restaurants, lounges and boutiques. I could see Mom’s face instantly relax, and after we passed by Starbucks, Cartier and Gucci, she even smiled. Amid the high-dollar tourist traps, I spotted a small, plain store called All White Clothing, which instantly stood out. 

“Let’s go check that place out. I bet they do Santería in there,” I joked, alluding to the white clothes worn by practitioners of the Afro-Caribbean religion. But Mom didn’t find it funny. “Are you nuts?” she said. “We’re not going in there.”

Not for the first time, I reminded myself that she was my mother and I loved her. We didn’t see each other very often (I live in Houston; she in Philadelphia), and Mom, who’s originally from Peru, rarely travels beyond the U.S. mainland. So the trip was a big deal for both of us. But while I wanted to see the parts of San Juan that weren’t in the guidebooks, she was looking for a luxurious respite.

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The coastline by Condado

Up until our pilgrimage, everything I knew about the U.S. territory I’d learned in North Philly, which has a large Puerto Rican population. During summers, reggaetón and hip-hop echo from cars roaming the area at all hours of the day, residents hang out on their front steps drinking beer and people-watching, young girls jump rope, and elderly men push carts selling quenepas (Spanish limes) and piraguas (shaved ice). The city’s annual Puerto Rican Day Parade takes place here and occasionally makes headlines for getting out of hand. Although it’s a vibrant community, North Philly isn’t what you’d call beautiful. Needless to say, my mom avoids it whenever possible.

Puerto Rico itself has been undergoing economic troubles for the last decade. With a debt of up to $123 billion, the territory filed for bankruptcy this past May. Zika fears, meanwhile, have hit the tourism industry, but the island still attracts millions of visitors each year, drawn not only to its rich culture, but also to its 270 miles of picturesque white-sand beaches.

When we arrived at our hotel and a greeter named Gustavo immediately offered us glasses of Champagne, my mother beamed with approval. The Condado Vanderbilt, built in the Spanish Colonial Revival style and overlooking the Atlantic Ocean, breathes opulence, from its marble floors to its high ceilings to its grand lobby staircase.

Built in 1919, the hotel was the first ritzy resort on the island, welcoming guests including Franklin Roosevelt, Charles Lindbergh and Errol Flynn. Through multiple closings, reopenings and remodels over the last century—including a recently completed $200 million facelift—it’s retained its hotspot status. 

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Condado Vanderbilt Hotel

Our room was breathtaking: a spacious suite with two balconies offering views of the ocean and city, where we watched the sun rise each morning, coffee in hand. At night, French macarons, soft robes and slippers were laid out for us. “This is how you should vacation,” my mother said happily, taking reams of photos and videos. It was hard to argue with her.

Mealtimes are always challenging for my mother and me, because we’re both vegetarian. But soon enough we discovered Latin Star, a quaint restaurant near our hotel. Far from fancy, this little gem is where the locals eat, but even Mom was happy here. We ordered mofongo, a mound of fried, mashed green plantains stuffed with veggies and topped with a tomato-garlic sauce—the seafood and beef versions are also popular—along with rice and beans, tostones (fried plantains), and piña coladas served in pineapples.

The next day we explored historic Old San Juan, which was once home to the territory’s military bases. Jammed with monuments and interesting architectural details—its colonial buildings are painted in bright pinks, yellows, reds and blues—the area is a window into the island’s rich past, dating back to when Juan Ponce de León founded Puerto Rico's first European settlement in 1508.

I felt transported through centuries as we walked along the cobblestone streets, past men selling fresh coconuts, tamarind piraguas and homemade coconut macaroons, reminding me of my hometown. My mom and I peeked into museums, restaurants, bars and shops—in one, I bought her an evil-eye charm bracelet, the better to protect us, I joked, if we decided to venture into the all-white-clothing store.

Soon, we found our way into the Cathedral of San Juan Bautista, the second oldest church in the Western Hemisphere and final resting place of Ponce de León, and the ocean-side Castillo de San Felipe del Morro, which was built in the 1500s to protect the city from seaborne enemies. It’s now a tourist attraction you can explore for $5; for no fee at all, you can hang out on its grassy square, take social media-worthy selfies and fly kites.

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Calle San Sebastian, filled with shops, bars and restaurants

Through the rest of the trip, my mom and I each had our small victories. Every morning, she insisted we breakfast at Ben & Jerry’s, where she ordered the same açai bowl and egg-white vegetable omelet that I’d wanted to try at a local food truck across the street. We went zip-lining through the mountains of Orocovis, hiked the trails of El Yunque, and—victory for me—hung out at a fruit stand on the side of a road in a random town, where we ate fresh coconuts that a farmer sliced in half for us with his machete.

At each place we visited, my mother found herself relaxing and chatting with the locals, who happily boasted about their island, and the tourists, one of whom was traveling alone and, over cocktails, confided in Mom and me about her recent divorce and affair. “Who would ever travel by themselves to a place like this?” my mother mused. “It’s kind of sad.”

“I think that’s pretty cool,” I said, a little defensively. “She can do whatever she wants.”

The last afternoon of our trip, we visited Luquillo Beach, an hour drive from Condado. The hotel concierge had recommended the attraction as a place unsullied by tourists. While it was pretty, and seemingly locals-only, it was seriously packed. We couldn’t even find anywhere to lay down our towels. We walked around in search of a comfortable spot, surrounded by a raucous party. “Oh wow, this looks just like Philly,” I observed. I could tell that my mom was longing for a nice cabana at the Vanderbilt, and if I’m honest, I was, too. We walked back to the car, and spent the rest of the day on our private, quiet, little beach.

In the end, we managed to find some middle ground, and we both loved the trip. If I return, though—and I plan to—I’m definitely going to find out what’s inside that all-white-clothing store.

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El Yunque National Forest

Insider Tips


  • Verde Mesa, the island’s most popular vegetarian- and pescatarian-friendly, organic farm-to-table eatery, serves up unique plates including octopus quinoa salad, ratatouille and a veggie medley over jasmine rice.
  • Both Barrachina in Old San Juan and the Caribe Hilton’s cariBar in Condado claim to have invented the piña colada. Order one at each bar, then decide who makes the island’s signature drink better. 



  • Hike the guided trails of El Yunque National Forest, a tropical rainforest located in the eastern region of Puerto Rico, offering over 28,000 acres filled with incredible flora, fauna and waterfalls. At dusk, kayak through the bioluminescent mosquito bay in Vieques, filled with glowing microorganisms.
  • Explore the 500-year-old San Juan National Historic Site, whose historic structures include the Castillo San Felipe del Morro, Castillo San Cristobal, Fortín San Juan de la Cruz, and San Juan’s city walls.
  • Tour Casa Blanca, a museum showcasing 16th- and 17th-century artifacts that was originally constructed as a home and fort for Ponce de León, who died before its completion.
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