4 Days in San Juan: More Than Just a Pretty Beach (At Christmas!)

I’ve been to Puerto Rico several times now. It’s quick, beautiful, relatively affordable and incredibly easy to visit from the mainland U.S. Unlike most other islands in the Caribbean, because Puerto Rico is a U.S. territory, getting there is domestic travel—no passport or international border control required.

From DC, you can be in Puerto Rico and on the beach in under five hours. But one of the reasons we keep going back is that Puerto Rico gives us something I find harder to get on a Caribbean vacation—plenty more to do when we’re ready to get off the beach.

When my kids were younger, that mattered a lot less. We would typically stay about an hour outside of San Juan at one of the big resorts in Rio Grande, where we spent most of our days swimming at the beach and pool and eating at the resort restaurants. We occasionally ventured out for an organized excursion to El Yunque or a half-day catamaran ride, but generally, the kids were happy to stay at the resort, and I was happy to keep the kids happy.

As they’ve gotten older—and become more seasoned travelers—they’re generally looking for more to do than just lie in the sun. And I definitely am. On our more recent trips to Puerto Rico, we’ve stayed closer to Old San Juan, where we can have the beach trip we want without making it the entire vacation.

That was especially appealing when we decided to sneak away for four nights just before Christmas in 2024.

Christmas, Caribbean Style

We stayed at the Condado Vanderbilt Hotel on Condado Beach, about a mile outside of Old San Juan. It gave us exactly the mix we were looking for: warm Caribbean mornings, afternoons by the pool, a little adventure, a little culture, and Christmas trees glowing against a backdrop of palm trees and blue water.

As always, on arrival day I prioritize getting to the hotel and getting settled. But Puerto Rico is a much quicker and easier trip from DC than an overnight flight to Europe, so I don’t mind having a couple of loose plans for that first day.

We arrived before check-in, and the hotel happily held our bags while we explored. After checking out the pools, lobby and restaurants, we eventually perched ourselves at the outdoor bar overlooking the Atlantic, where we ordered drinks and shared a few appetizers while we waited for our room.

Not a bad way to kill time before check-in.

Once we were settled, we didn’t venture far for dinner. That night we had reservations at STK, one of the hotel’s four full-service restaurants.

STK is a chain steakhouse with locations in major cities around the world. The steaks are good, the atmosphere is chic and trendy, and it is expensive. Very expensive.

But for night one, I was willing to splurge. I liked the ease of eating right at the hotel, the familiarity of a brand-name steakhouse after a travel day and, perhaps most importantly to my daughters, a little Instagrammability.

Sometimes arrival night doesn’t need to be more complicated than that.

Sea Turtles Before Christmas

On day two, I woke up early, before my girls, and headed out for my usual morning walk. The hotel already had coffee waiting in the lobby with all the trimmings, and it was good. Each morning, I added a little cinnamon to my typical unsweetened coffee with a dash of milk—a tiny reminder to myself that I was on vacation and should enjoy the little things.

Coffee in hand, I slipped out of the hotel and walked along Condado Beach in the sand.

Condado Beach is a long stretch of sandy coastline lined with large hotels, restaurants and plenty of places catering to beachgoers. In some ways, it might remind Americans of many other East Coast beach towns, with souvenir shops, seafood restaurants, ice cream and people everywhere on foot and bike.

But early in the morning, it’s different. The beach is quiet, the sand is mostly empty and a walk along the water can be wonderfully meditative. By 10 a.m., you’ll be dodging umbrellas and families. At 7 a.m., I practically had the place to myself.

Eventually, my girls woke up and we spent the rest of the morning stuffing ourselves at the hotel’s wonderful breakfast buffet before heading out for our anchor activity of the day: snorkeling with sea turtles!

Our snorkeling spot was only about a mile and a half from the hotel at Parque Acuático del Escambrón. If we had been in Europe, we probably would have walked the mile and a half. Here in Puerto Rico, we Ubered.

At the park, we met our guide and fellow snorkelers for some quick instructions and equipment fitting before trudging through the sand in our flippers and into the calm waters of the cove.

For the next 90 minutes, we followed our guide through the warm, clear Caribbean water looking for sea turtles and colorful tropical fish.

We saw them all.

There is something pretty incredible about floating in the Caribbean while a sea turtle swims by below you. And as a bonus, our guide took photos and videos throughout the excursion and transferred them to us afterward, so we came home with some pretty awesome digital keepsakes.

Back on the beach, families were suntanning and playing in the sand while vendors sold coconuts and fruit bowls sprinkled with Tajín. We got one of each and sat in the hot Puerto Rican sun enjoying them while we waited for our Uber back to the hotel.

Not exactly how I usually spend an afternoon a few days before Christmas.

That evening, we ventured out a little farther for dinner—but not much. Condado sits on a narrow strip of land with the Atlantic Ocean on one side and the much calmer Condado Lagoon on the other. We crossed over to the lagoon side and ate outside at a little sushi restaurant overlooking the water.

Unfortunately, when I checked recently, the restaurant had been replaced by something else. But Condado is packed with restaurants within easy walking distance, so rather than send you somewhere I can no longer personally recommend, I’d suggest checking current reviews and choosing whatever sounds good to you.

My only recommendation? Sit outside.

You’re in Puerto Rico in December. You might as well make your friends and family back home a little jealous.

Christmas Trees, Cobblestones and Cats

Day three started with my now-established morning ritual: coffee, walk, pitter-patter around until the girls woke up.

One thing that can make or break a hotel for me is morning coffee access. And I don’t just mean a coffee maker in my room. I want decently brewed coffee, prepared and waiting for me at an early hour, preferably in a to-go cup so I can take it on my walk.

If there’s no coffee out by 6:30 a.m., I’m annoyed. If there’s no coffee by 7 a.m., that is unacceptable.

I don’t need a barista preparing me a matcha latte or a flat white. I just need a decent cup of coffee that I don’t have to make myself. The Condado Vanderbilt had a nice coffee and tea setup ready by 6 a.m.—plus cinnamon for sprinkling!—and I was a very happy camper.

Day three was also our least beach-centric day. We had booked a guided group tour of Old San Juan, and our tour bus picked us up right from the hotel lobby. After circling through Condado to collect guests from several other resorts, we made the short drive into Old San Juan and set off on foot for our three-hour tour.

We’ve done a lot of walking tours in cities around the world, and I’ll admit my expectations for this one weren’t particularly high. But I was pleasantly surprised.

Old San Juan is colorful, compact, walkable and packed with history. We wandered through local markets where vendors sold food, produce and handmade goods, and we picked up some of my favorite kinds of souvenirs—the things you’re unlikely to find in an airport gift shop. We bought handmade soaps and a leather belt that the shop owner measured and cut to size right in front of us.

From there, we walked the cobblestone streets past monuments, rows of brightly colored colonial buildings and along the old city walls, now part of a UNESCO World Heritage Site, with huge views of the Atlantic stretching out beyond them. It’s hard to walk very far in Old San Juan without being reminded just how old the city is.

Our tour stopped at the Catedral de San Juan, which dates to 1535 and is one of the oldest cathedrals in the Americas. We also visited Castillo San Felipe del Morro, better known as El Morro, the massive Spanish fortress whose construction began in 1539 to protect the entrance to San Juan Bay. Standing among centuries-old stone walls with the Atlantic stretching out below felt worlds away from the resort and pool we had left behind that morning.

And because it was December, Christmas followed us here too.

The colorful houses were dressed up with lights, garland and holiday decorations. There was something slightly surreal about seeing all those familiar signs of Christmas surrounded by palm trees, bright sunshine and the blue Caribbean sky. For a girl whose Christmas weather conversations usually revolve around, “Do you think we’ll get a white Christmas?” it was a pretty dramatic change of scenery.

And then there were the cats.

So. Many. Cats.

Maybe as many as Athens! I might have taken as many pictures of cats climbing trees and lounging around Old San Juan as I did of the incredible ocean views.

Eventually, our tour dropped us in the center of town for some free time and lunch.

By then, the girls and I were hot and ready for two things: a seat and air conditioning.

We found a local Puerto Rican restaurant and ordered a table full of specialties, including croquettes and mofongo—a classic Puerto Rican dish made from fried green plantains that are mashed with garlic and other seasonings and then often served with meat or seafood. I ordered mine with skirt steak.

And, for me a mojito.

After lunch, we met back up with our group for the ride to Condado. Looking out the bus window, I noticed Christmas trees glowing inside the windows of high-rise apartments overlooking blue water and sandy beaches.

Christmas trees. High-rises. Palm trees. Beach.

There was something about the combination that I loved.

Maybe because it was exactly why we had come.

We wanted Christmas—but we also wanted a little break from Christmas as we normally knew it.

Back at the hotel, we spent the rest of the afternoon doing absolutely nothing ambitious, lounging by the pool, reading and listening to music. I can’t remember exactly what I was reading, but knowing me, it was probably a copy of Condé Nast Traveler or Travel + Leisure, already inspiring next year’s holiday trip.

Even being on vacation does not stop me from thinking about my next vacation.

Doing Plenty, and Absolutely Nothing

Our fourth and final full day was devoted almost entirely to relaxation.

We spent a slow, sunny morning by the pool and beach before heading to the hotel’s spa, where each of us had booked a treatment. And because my girls and I may love a good adventure, but we are also always ready for a day of pampering, we made sure to take full advantage of the spa facilities included with our treatments too.

The spa was tranquil, quiet and exactly what I wanted after a few days of sun and exploring. Before my massage, I settled in with a cup of hot tea amid low lights and quiet music. Afterward, I took my time in the sauna and enjoyed a long, hot shower with all of the spa’s luxurious products.

There was nowhere we needed to be. Nothing left on the itinerary that we needed to check off.

And that was the point.

We capped off our relaxation day with dinner at the hotel’s oceanfront Tacos & Tequila restaurant, eating seafood tacos overlooking the Atlantic without ever having to leave the property.

Later that night, I sat out on our balcony feeling the warm island breeze against my saltwater-sticky skin.

And I purposely looked around for Christmas.

By then, I had gotten used to seeing it in unexpected places. Holiday lights decorated restaurant patios. Christmas trees glowed through apartment windows. Festively-lit balconies twinkled above palm trees, and somewhere beyond them was the dark Atlantic Ocean.

Four days earlier, sitting outside in a bathing suit and sipping a mojito had made it easy to forget it was December. Now, I found myself noticing all the little reminders that Christmas had been there all along.

This trip had been exactly what I wanted it to be. We had snorkeled with sea turtles and wandered centuries-old streets. We had eaten mofongo and seafood tacos, spent hours by the pool, explored Old San Juan and devoted an entire afternoon to the spa. We had done plenty—and also absolutely nothing.

And somehow, Christmas had woven itself through all of it.

I don’t think a warm-weather Christmas will ever replace the version I love at home. I still want the cold air, the familiar traditions and, yes, I’ll always wonder whether we might get a white Christmas.

But for a few days, it was fun to trade all of that for palm trees, blue water and mojitos.

Sitting on that balcony, surrounded by Christmas lights and warm Caribbean air, I felt completely content.

And ready to go home for Christmas.