For the 50+ Traveler

Lush, tropical, and utterly charming, Puerto Rico is a delight for travelers looking for a beach break with a hefty side of history. The island, a territory of the United States since 1898, sits in the northeastern Caribbean and has been a center of commerce and shipping for centuries.

Its capital, San Juan, sits right on the Atlantic coast. It’s an old city -- founded in 1521 by Spanish colonists, the port is a melting pot where Taino (the island’s native culture), African, and Latin influences can all be found.

Here are some of the best things to do in this Caribbean capital.

View from the fortress of El Morro.
Erika Ebsworth-Goold

1. Explore The Fortresses

The massive gates that define San Juan’s shoreline -- Castillo San Felipe del Morro (El Morro to the locals) and Castillo San Cristobal -- are part of a U.S. National Historic Site. San Juan was under near-constant threat by other European forces, not to mention pirates. Both of these stone fortresses were built by Spain to protect the city, which was an important strategic entryway into the Caribbean.

El Morro provides a high vantage point over San Juan Bay and was well fortified with weapons and soldiers. San Cristobal, just east of Old San Juan, provided defense from land attacks; it was here where the first shots of the Spanish-American War were fired. Both fortresses are maintained by the National Park Service. While you can freely climb and explore most of El Morro, you must pay a $10 park fee to access San Cristobal.

2. Light A Candle At San Juan Bautista Cathedral

The beating heart of Catholic San Juan, San Juan Bautista Cathedral -- built in 1540 -- is the second-oldest cathedral in the Americas (and the oldest on U.S. soil).

This is where San Juan’s founder, Juan Ponce de Leon, one of the most famous Spanish colonists, is buried. According to tradition, he was the first European to reach Florida. He was searching for the mythical fountain of youth, but he clearly didn't find it -- he died in Cuba and was brought back to the city he founded to be buried. You’ll see his ornate tomb in the cathedral, as well as the body of Saint Pio, a Roman martyr who was killed for his faith. His remains, covered in wax, rest in a glass box on the left side of the cathedral.

There isn’t an admission fee to access the cathedral, but donations are accepted.

The writer with her family at San Juan's tiniest home.
Erika Ebsworth-Goold

3. Take A Selfie At San Juan’s Tiniest Home

As you wander San Juan in the area near El Morro, you might stumble upon what some say is the world’s narrowest house. Called La Casa Estrecha, or the Narrow House, this petite dwelling, sandwiched between two much larger structures, is just 5 feet wide! Once a small alleyway, it was converted into a functional -- yet quirky -- living space by a local architect. You’ll know it when you see it, thanks to its diminutive width and bright yellow paint.

Tours of the interior can be arranged in advance for $5.

4. Pray For A Miracle At Capilla Del Santo Cristo De La Salud

Looking for a miracle? Head to Old San Juan’s Capilla del Santo Cristo de la Salud, a tiny iron-gated chapel overlooking the sea.

Legend has it that in the 1750s, during an annual horse race, a rider plunged down the nearby cliff but somehow survived… and that this little chapel was built to celebrate his good fortune. While we hate to let reality get in the way of a great story, the truth is that the young man died, and the chapel was built here to prevent future tragedies.

No matter its origin story, this is the place the people of San Juan still go to pray for miracles. The tiny chapel is only open on Tuesdays. It’s next door to a large, pigeon-filled plaza where people go to feed the massive flocks of birds. (We skipped it in an attempt to avoid getting dive-bombed!)

Architecture in San Juan, Puerto Rico.
Erika Ebsworth-Goold

5. Admire The Architecture

San Juan is a beautiful mash-up of all sorts of architectural styles and designs. While this shouldn’t be surprising, given the city’s age, it's a marvel to see it all blend together. Spanish Colonial, Gothic, Renaissance, and Baroque styles mesh seamlessly with Art Deco and Arabesque window arches and tilework. Pay attention to the building facades as you meander by; you’ll spy little surprises and delights in most, even if you’re not an architect by profession.

6. Take A Trip Back In Time At Casa Blanca

To get off the tourist trail and take in some San Juan history, put Casa Blanca on your itinerary. This home was built for Ponce de Leon’s family in 1521 and also served as the city’s first fortress. Today, the 500-year-old compound is a museum full of 16th- and 17th-century artifacts maintained by the Institute of Puerto Rican Culture. While the furniture isn’t original, it does give visitors a feel for what life was like for colonists during San Juan’s early days. The gardens are gorgeous and well worth a stroll.

Casa Blanca is free to visit, and it’s open Wednesday through Sunday.

A piña colada from Barrachina in San Juan.

7. Grab A Pina Colada At The Spot Where The Drink Was Invented

When you’re ready for a cocktail break, head to Barrachina. This restaurant, tucked into a courtyard off of Fortaleza Street, was originally famous for its paella. But back in 1963, as the plaque out front explains, bartender Don Ramon Portas Mingot created the sweet concoction now known world over as the pina colada.

Barrachina still serves up the classic rum, pineapple, and coconut drink in frozen form, complete with a cocktail umbrella garnish. It’s kitschy, touristy fun to stop in and enjoy a frosty pina colada -- and perhaps a quick snack -- before continuing your San Juan adventures.

8. Enjoy A Paleta In The Plaza -- Any Plaza

The people-watching in San Juan is absolutely terrific. So, when you’re ready to take a quick break, we recommend stopping into any paleta shop, grabbing one of the frozen fruit pops (mango was our favorite!), and plopping down on a bench in any of San Juan’s numerous tree-shaded plazas. Rest your feet, enjoy your treat, and take in the views -- of the bay, the overall scene, and the people who make this city their home.

9. Check Out The After-Hours Arts And Culture Scene

San Juan has a rich tradition of performance arts -- especially music -- and you can easily experience that tradition when you visit.

For some of the best flamenco dancing in the city (and yummy small plates), Triana Tapas is a terrific stop. It offers authentic live performances six nights a week. On Sundays, El Callejon de la Tanca comes alive with bomba y plena, traditional percussion music. Locals and tourists flock here to dance along to the music. Jazz aficionados know all about Carli’s Fine Bistro & Piano, located on the first floor of the historic Banco Popular building. This swanky spot has a club-like feel, with great dinner options and live jazz.

Poets Passage, a charming coffee shop and boutique on Calle Cruz, hosts open-mic poetry nights every Tuesday evening. It’s certainly a pace and scene set apart from the rest of the area, and it’s worth checking out.

10. Take A Culinary Tour Of Old San Juan

Something we tried -- and ended up loving -- was the eating/walking tour of Old San Juan. It was easy: We met our guide at a central location, and from there, we let her lead the way!

We had a small, fun group, learned all about the old section’s best-loved landmarks, and -- the best part -- we stopped at five different restaurants and cafes along the way. On these breaks, we sampled some of the city’s best food and snacks, including mofongo, empanadas, and of course, rum and chocolate.

This was some of the best money we spent on our trip. The 3-hour excursion cost about $100 per person, and we came away with both bellies and minds full. We booked through Flavors of San Juan, and we can’t say enough about the experience.