Like all members of the Greater Antilles squad these days, Puerto Rico has suffered a few hiccups: a crippled economy, a post-hurricane mop-up still in progress and riots in the streets over allegations of high-level government corruption and ex-Gov. Ricardo Rosselló’s not-so-woke chats.
But on the bright side, its bangin’ Daddy Yankee-graced beaches are still open for biz — and the island needs tourist bucks more than ever.
All the recent headlines swirling around Puerto Rico may be intimidating, but they shouldn’t be frightening — a trip there is about 1/1,000th as scary as a typical SantaCon.
The vibe is back to positive on the pastel streets of Old San Juan.
San Juan’s protests earlier this year — largely led by women and held in the cobblestoned, rainbow-buildinged, historic streets of Old San Juan, the island’s oldest European settlement — resolved themselves quickly and peacefully. (Last week, flaxen-haired legal beagle Wanda Vázquez Garced was sworn in governor, but she’s more than a tad divisive, so keep updating your Indeed resume for the job!)
Bottom line: Don’t sweat the summer’s unrest and get prepped for a visit. Here’s how to enjoy Old San Juan now that the ever-fun, ever-sunny, ever-surfable coast is clear.
Where to shack up
The boys don wrinkle-free tuxes looking so fresh and so clean, their black hair scrupulously gelled and slicked back. Their female companions are florally perfumed and glammed out to the max, rocking thousand-dollar silk and satin dresses with trains rivaling New York Times Vows brides (it’s tricky not stepping on them in the elevators).
The newly reopened and historic Caribe Hilton (from $245) — which closed just under a year and a half ago and poured $150 million into fully renovating itself after being walloped by Hurricane Maria — is hosting prom/grad night for the elite all-boys Colegio San Ignacio prep school.
At the newly renovated Caribe Hilton, say buenas días to that hardy San Juan sun.Caribe Hilton
In Puerto Rico, prom is no joke. Along with their dates, seniors invite their moms, dads, sisters, brothers, grandparents — the whole dang family tree and whatever other sprigs they can find. You might think that would kill the usual birds-and-the-bees vibe the night is supposed to promise — but in zesty PR, young love is alive and well and openly fueled (the drinking age is 18).
Good PR: Their booze is safe!
This night exemplifies the perfect motif for 2019’s Puerto Rico: transition. For the students, it’s adolescence into adulthood, love, college life and beyond. For this iconic septuagenarian, just-reopened hotel — whose Caribar claims paternity over the piña colada, birth date 1954, thanks to OG mixologist Ramón “Monchito” Marrero — and the island writ large, they’re moving on from myriad hardships to renewed prosperity and hope.
For guests of the 17-acre beachfront property — whose sheets have been crinkled by the likes of Barack Obama, Liz Taylor and Gloria Swanson over the years — Caribe Hilton offers 652 fresh new rooms. Recreationalists will delight in the Monica Puig Tennis Center pro seminars (and if you’re not a vomitous heat-stroke sufferer like yours truly, you might actually learn a thing or two and not almost die). Also, scuba and snorkeling needn’t be a Sophie’s choice: 1-hour snuba sessions are available for $70 through on-site Aqua Adventure (unless it’s raining out, which it usually does in this part of the world, every day, for like 10 to 15 minutes).
After all that, piña coladas at the swim-up pool bar are off-the-record mandatory. No prom date required.
Do something, why don’tcha?
Old San Juan is for the birds — and they’re more than human-friendly, when bribed with food.
The best tour of Old San Juan is organized by the lovely Leslie Padró — a three-hour, guided walking food/booze tour through the storied, Hitchcockianly pigeoned streets of Old San Juan (89.99).
A Georgia-born, UGA-educated, self-proclaimed “sorta Rican,” the maverick Flavors of San Juan Food founder will provide a pilot (mine was the delightful Nadia) who’ll introduce you to coffee and ham+cheese croissants at Cafe Cuatro Sombras; passion fruit popsicles that’ll permanently sticky-fy your hands from Senor Paleta; alcapurria infused (or, more honestly, nuclearized) with pique hot sauce at Café El Punto; DIY mofungo at The Old San Juan Parrot; capping it all off with hot chocolate and cheese (Nadia’s grandmother’s favorite — trust us, the pairing somehow works) at Casa Cortes Chocobar.
A little light exercise on Condado Lagoon.
The freaks come out at night — especially in Condado Lagoon. That’s when and where the young crew at Night Kayak will guide tandem teams of paddlers with clear bottomed, LED-lit craft over the water and under bridges where you’ll (their disclaimer: maybe) hover over bait fish, lobster, starfish, turtles and stingrays ($49).
Don’t worry, after an hour of verbally sparring with your kayak-mate/“accidentally” hitting him or her with a paddle, you’ll find your mutual rhythm. Solo SUP is an option, too.
Where to eat & drink
If you can’t bear one more friggin’ piña colada, mojito or any other drink ending in a vowel — good as they may be! — there’s hope. Probably the most doesn’t-belong, out-of-place, misfit watering hole in all of the city is Murphy’s Law Irish Pub, in New San Juan, which serves up Guinness and Duck Fart shots (Kahlua, Bailey’s Irish Cream, whiskey) along with chalkboard-written modern Gaelic-inspired quips about drunken texting and whatnot.
For lunch, head to the rough-around-the-edges Old San Juan ‘hood of La Perla (whose mean streets, fun fact, served as the venue for the “Despacito” music video). There you’ll find scenery-spoiled La Garita, a small, somewhat bathroom-challenged, open-air (and mercifully breezy) restaurant whose wait staff definitely operates on island time and whose Spanglished menu is equally surfed and turfed.
And speaking of, the views of the actual surf, a quick hike down below you, and the surrounding, narrowly streeted turf (with cement-block homes still roof-tarped from the especially severe lashing Maria gave to this coastal part of Old San Juan) are mind-blowing.
Good tunes always aid and abet good digestion. Head back to San Juan proper and into Sabrina (named for the Hepburn flick), a never uncrowded bistro offering live music to cut a Boricua rug to between bites of tropical cuisine.
We had a great time with Hector! He was a great tour guide!
Fantastic tour - great historic and cultural insights by fun, knowledgeable and easy-going guide, Leslie Ann!
While all the food is still fresh in my belly let me take the time to give a shout out to my boy Hector for being such an amazing guide!! He was super friendly and knowledgeable about the area. We had wonderful conversations about history, culture, places to go and of course food! This is well worth the price and you will be full afterwards. Our group was so fun and the weather was perfect! I’d recommend this tour for everyone (because of course we all need to eat) because now you know where to go back to eat and you’ve walked by various restaurants and can get your tour guide’s opinions about them. Oh and make sure to wear comfortable shoes!
Pablo knows his country. He gave us all the history we could possibly wants. A very knowledgeable young man. We would definitely recommend this tour to anyone who visit PR.
Thank you for a great experience.
Great guide. Fun tour. Definitely recommend it!
Marjorie was the BEST! Our group of 8, including 4 kids, thoroughly enjoyed our food tour of Old San Juan with Marjorie. She was friendly, upbeat, and shared tons of interesting information. We loved learning from her and tasting so many San Juan delights. Highly recommend Marjorie and this tour. It was the perfect kick off to our week in San Juan.
This was such a wonderful introduction to Puerto Rican food, history, and culture. Our guide, Marjorie, was a delight and made this tour so fun!
Fabian was a great tour guide. The food was delicious and information helpful.
Marjorie was a very knowledgeable and enjoyable guide!
Google rating score: 4.9 of 5, based on 451 reviews
Flavors of San Juan® knows the island is so much more than its beaches and invites visitors to progressively dine with us in a safe, sustainable and environmentally responsible manner.