You might as well call us Mr. and Mrs. Puerto-Retersik—we recently slipped away for a few days to celebrate our 10th wedding anniversary in Puerto Rico. Puerto-Retersik does roll right off the tongue if you try hard enough. Promise.
As we mentioned on last week’s podcast, we wanted to share pictures and details from our anniversary trip to San Juan because we absolutely loved it and highly recommend it. Below is a concise guide to where we stayed, what we did, and what we ate—useful if you’re considering a trip to the area.
Why Puerto Rico?
After taking an “adventure honeymoon” to Anchorage, Alaska in 2007, for our 10th anniversary we wanted somewhere beachy and relaxing. Puerto Rico fit the bill: short flights from the East Coast meant more time away and less travel, and as a U.S. territory there were no passports or currency exchange hassles. Spanish is the primary language, but English is widely spoken and locals were extremely kind. Aside from deciphering a few street signs, we had zero language trouble.
Where We Stayed:
We followed the “get a modest room in a nice hotel” tip and stayed at the Condado Vanderbilt Hotel in San Juan, about five minutes from Old San Juan. We found a package deal with flights and hotel during low season that made the trip very budget friendly. The hotel offered multiple pools, restaurants, and plenty of amenities, so you could stay on property the whole time if you wanted to fully unwind.
We had 3.5 days and spent at least one day entirely relaxing—lounging poolside, reading, and ordering food directly to our chairs (the servers walked into the shallow pool area with tacos—yes, really). Mango tacos = Sherry’s happy place.
The property also had deck space, hammocks, a small lagoon, and an adjacent sandy beach. One memorable spa surprise: I booked a couples massage for us—small throwback to our honeymoon—and the spa included a private lounge to relax in afterward. We enjoyed admiring the outdoor furniture and planters while we unwound.
What We Did – Adventure Day:
We spent two full days exploring. Our first “adventure day” involved renting a car, driving about an hour east to Fajardo, and combining hiking with a nighttime kayak tour of a bioluminescent bay. These bays contain microscopic organisms that glow when disturbed—stir the water and it sparkles.
On the way, we stopped at Luquillo beach and the famous food kiosks—open-air stalls offering authentic Puerto Rican dishes. There we tried mofongo (mashed plantains topped with chicken and peppers), which was fantastic.
Next we visited El Yunque National Forest, the only tropical rainforest in the U.S. National Park System. With limited time, the visitor center recommended the La Mina Waterfall hike, which delivered lovely scenery and an enjoyable hike even without swimming at dusk.
We also stopped by an observation tower area for views, and took a playful recreation of a wedding-hand photo we took on our honeymoon—all nice little moments along the drive.
For the bioluminescent tour we used Kayaking Puerto Rico, a professional and reassuring operator that many on our tour recommended. We timed the trip for maximum darkness; a full moon made the paddle beautiful but slightly reduced the visibility of the bioluminescence. Guides sometimes used a tarp to enhance the effect, and when you stirred the water it truly looked like glitter in the dark. Paddleboarding and kayaking through tree-canopied channels at night was an unforgettable experience.
We returned late but found energy for the hotel’s 24-hour hot tub—quiet and relaxing after a long day.
What We Did – Culture Day:
Our “culture day” focused on history and Old San Juan. A short Uber ride took us to Castillo San Cristóbal, where part of the fort happened to be used for a film shoot. Despite some areas being closed off, the fort offered plenty of fascinating sights and atmosphere.
The forts’ iconic sentry boxes, or garitas, are a must-see and make for great photos. We also spotted iguanas wandering the grounds—perfect for kids and quirky photo ops.
We walked between the two forts instead of taking the trolley and loved strolling Old San Juan’s streets—colorful buildings, ornate balconies, and charming doorways at every turn. The neighborhood is ideal for meandering, taking photos, and discovering outdoor cafés and tapas spots.
We toured Castillo San Felipe del Morro next, which is expansive and impressive. Wear comfortable shoes—there’s a lot of walking, stairs, and ramps—and make sure you have room on your phone for photos.
After the forts we enjoyed a tapas lunch in a courtyard and kept exploring, grabbing treats and wandering through lively plazas with pigeons and street life. Random moments—like feeding a friendly bird—made the day feel spontaneous and fun.
Squeezing In One More Adventure:
On our final morning we ate at a food truck near the hotel (the best taco I’ve ever had—crispy tortilla heaven) and then stood-up paddleboarded in the lagoon behind the hotel. To our surprise, there were manatees in the lagoon—yes, we paddleboarded with manatees. It was a gentle, joyful way to end the trip.
In short: we loved celebrating our tenth anniversary in Puerto Rico. The trip was relaxing, easy to plan (we booked a flight-and-hotel package and only reserved the kayak tour in advance), and full of memorable activities. It made us more excited about future family travels—if we can do a low-fuss getaway like this, bringing the kids feels a lot less intimidating. Happy travels, amigos!