San Juan, Puerto Rico Was The Travel Itch Cure We Needed

The last time I set foot on Puerto Rican soil was back in 2009 while doing a shore excursion on my first gay cruise. The 8-hour stay was enough to do the touristy rum tour, self-guided sight-seeing tour of Old San Juan, and visit to the local ribbit ribbit food/bar chain restaurant and that was about it. My time there was just like that last sentence, too hyphenated.

February found me all set to go to really give PR a go, but when the newest COVID string popped up it pooped on my plans as travel was once again a little iffy and cumbersome. And at the time Puerto Rico was requiring a negative PCR COVID test before coming to the island and the US was still requiring one to get back in.

Not the case anymore. June found me setting foot in Puerto Rico for the second time and this one was to be different than the last.


Where Did We Stay?

Tons of cute and exceptional places to stay in Puerto Rico can be found, but to celebrate my true first overnight visit I would be residing at the Caribe Hilton (@caribehilton)


The historic and iconic Caribe Hilton is situated on a private 17-acre lushly landscaped peninsula with a secluded beach and is located near the Old San Juan historic district and many of the destination’s top attractions. When you arrive at Caribe Hilton, you’ll find more than just a place to stay – it’s a place to come alive. With 652 recently renovated rooms and suites to choose from, discover a vacation that is as comfortable as it is memorable.

Never did I feel that there were so many rooms or this resort-like hotel was able to accommodate so many people. Caribe Hilton was completely renovated after Hurricane Maria. I’ve been to many modern Caribbean hotels and resorts and this one has what it takes to stand tall among the best. The vacation began when the Uber door opened and you were greeted with the expansive open concept lobby and views from every spot you could stand in.

Pausing to check in, my glance could not be stopped as it went to the Caribar and then to the pools and beautiful ocean side lounging.  Soon I would be at both the bar and the beach enjoying what the Caribe Hilton was offering me. I mean, if it’s there for the taking, I must oblige.

Caribar & Caribar Terrace – Our exciting destination bar, Caribar – the birthplace of the Piña Colada – presents hand-crafted cocktails and a delicious tapas menu in an iconic setting – with panoramic ocean views, of course. Taste the evolution of the Piña Colada, from the original recipe that was created right here at the hotel in 1954 to global variations, including our contemporary version: The Clear Colada.


What To See & How To See It

One thing that I have been a fan of doing recently when traveling is either downloading a self-guided tour, (Nashville Mural Walk), or an inexpensive app tour with pics, GPS, and audio (New Orleans Garden District), or finding a tour and letting someone else take the lead or wheel (Asheville Rooftop Bar Tour, Merida Free Downtown Walking Tour, Medellin Graffiti Tour).  What to do in San Juan? The Art Walk PR (@theartwalkpr).

Since my Spanish is basically nonexistent, a guided tour in both Medellin and now San Juan was in order. The Art Walk PR brought us into the heart of the art district of San Juan.  No, not to the pricey and well air conditioned art galleries, but down to where the artists still live and create. Our tour guide Georgie Vega was a true asset for as she shared her knowledge of the history, politics, and art movements of San Juan, artists would be saying hello to her and we would be drawn into new exhibits or ones in the process.  We actually took part in one of the art exhibits, added our paint strokes to them, and it was there that I learned that artist Javier Cintron was a friend of a friend and we had a great connection to Maine where I grew up and he lived at one time.  A very small world. 

Guided art walk through the murals at La Calle Cerra (Cerra Street). Santurce has world-class street art and hosts the Santurce es Ley street art festival every year. Explore the murals in Calle Cerra, striking large-scale work by local and international artists like D’Face (London), Fintan Magee (Australia) Bik Ismo (Puerto Rico), David Zayas (Puerto Rico), Ana Marietta (Puerto Rico) Evaristo Angurria (Dom. Rep), Danae Brissonet (Canada) among others.

The emerging Santurce neighborhood is the art and nightlife nexus of San Juan. For the last 15 years, the cheap rents in the traditionally working-class neighborhood have been steadily attracting artists. Today, formerly rundown buildings are canvases for vibrant street art, house James Beard Award-nominated restaurants, and invite the LGBTQ community to dance deep into the night.


By the way, San Juan can be hot. It felt similar to Florida weather, but when the chance came up to end the tour at a bar/restaurant, yeah, that was good planning.

Guarare (@guararelacerra) supplied a cool breeze, high ceilings, my first taste of mofongo. And of course, I ordered the drink that involved lavender smoke and a great presentation.  I didn’t know, felt bad, but it was worth it on my end, but of course I didn’t have to make it.


Letting Someone Else Lead Us Through The Night

For one of our nights in Puerto Rico, dinner and drinks were combined in another San Juan tour offering. The Spoon Experience (@thespoonexperience) took over our plans for the evening. It wasn’t just the great restaurant we started off at, but the overall evening was just a nice stress-free experience.  Someone else took over the pace, the planning, and payments as tours will let you know what is included or not and we were happy with the package.  If you don’t like any tour’s offerings 100%, ask them and most tours will cater to your needs and alter what needs to be changed to make you happy.

We were very happy to see that San Juan does have a restaurant week and we happened to be there for this joy. SUMA MESA + BARRA was the first stop on our spoon experience. Rooftop dining provided an ambiance and breeze that set the mood for a great night, and our waiter was a pleasure.

We were lead around a couple bars on Calle San Sebastian, enjoying adult libations, looking at the pretty people, meeting Joedh the manager of Cafetín (@el_cafetin_1)and Joey, a manager at La Factoría (@lafactoriapr).  Cafetín was a very mixed bar from grandmas almost knocking the doors off the place to the shy little “OMG they look so you, but I’m so old” boys. Transgender patrons, hot bartenders, and everyone and anyone showed up in wave after wave. I could have stayed there all night, but La Factoria is a place that we’ve heard so much about with its 6 different venues under one roof, from a wine room to a back end brick bar that was uncovered during some renovations. Packed, hip, fun, definitely straight, but open for everyone.  Give the bars on Calle San Sebastian a try as it is the hub of the San Juan touristy bar scene and it was enjoyable.


Last Day Of Fun & Frolic

The previous night out at the bars was a fun night hence the brunch and not breakfast the next day. We popped over to Condado area of San Juan, a beach area and where we heard the gays go. Don’t hold me to that, but there were a ton of rainbow umbrellas (that everyone was using) and some men, male couples, and other men to look at. It was a little rainy and overcast day so it was not too busy, but it was a good time to eat at Wicked Lily(@wickedlilypr)


We had massages back at Caribe Hilton, oh yes, we did, which might have caused a nap time to occur. But rest up we did as we had reservations for La Central by Mario Pagan (@lacentralbymariopagan) located in DISTRITO T-Mobile (@distritotmobile). Yep, the phone company has sponsored an entertainment and dining center that I would love to see near me. We became fans of La Central by Mario Pagan. There was salad for some us that tried to be a little healthy, as well as cheese, steak, old fashions, and a dark country western ambiance that fit the mood and offerings well.

Afterward, we wandered around, watching families hang out, kids having fun, couples dancing, all around pride decorations. We know T-Mobile is a great ally and they showed it at DISTRITO T-Mobile.

DISTRITO T-Mobile – A unique five-acre experiential complex that combines the best in global retail, destination dining, art, entertainment, music, technology, and hospitality.

 Destined to be the most vibrant and popular setting for events, conventions and performances of all types in the Caribbean region, offering a multisensory, audiovisual, and technologically advanced experience, including an exhilarating urban zipline and a variety of restaurants, bars, lounges, featuring authentic and local rum, beer and cuisine.

I’m not a public salsa dancer but more of a singer so we ducked into Arena Medalla (@arenamedalla)for a Karaoke Night Experience that I had not had the likes of in a long time.  We were joined by native Puerto Ricans, fellow Americans, and a Brazilian. English, Spanish, and Portuguese was sung at varying volumes and quality, but was much more than a good time. Friends were made and new words were learned.


Do It All Again?

This visit to Puerto Rico was umpteen times better than the last as I saw more than a rum bottle, a fort, and a frog bar. Caribe Hilton was the great home base for this enhanced discovery of San Juan.  We did other things that were not mentioned, walked and saw other things. We did not take part in the other well-known Kweens Klub, Oasis, SX, or Toxic as many of the gays were in the beach town of Boquerón in Cabo Rojo, Puerto Rico celebrating Pride when we were there. Actually, some of the San Juan bars were closed so their workers could be on vacation and go to the west coast and celebrate.

A visit to Puerto Rico should be on your list to soon do. We were only there from Thursday to Sunday but the amount of decompression, relaxation, and just time to pause and reflect, so worth the journey. The money is the same and no passport is needed. There really is no language barrier and it’s an easy flight from many major east coast cities. I will return to San Juan and the next trip will include more of San Juan but also some of the beauty outside of the city.  Booking soon.

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