Puerto Rico really is the vacay gift that keeps on giving, with its lush green tropical forests, landscapes, and mountains, world-class surfing, vibrantly colored colonial architecture, quaint cobbled streets, white sandy beaches, sparkling blue sea, rich culture, buzzing nightlife, and fantastic food.
Added bonus? Despite the island being in the Caribbean, if you’re a USA citizen, you don’t even need a passport to visit. You can just skip past immigration and customs like you own the place. Which you kind of do — since Puerto Rico became a U.S. territory in 1898 following the end of the Spanish-American War.
Puerto Rico measures just 37,835 sq feet, making it about 1,080 times smaller than the United States. You can actually drive around the perimeter of the whole country in just one day. But what the “Island of Enchantment” lacks in size, it more than makes up for in substance.
Ready for some travel again? Then plunge into Puerto Rico with our ultimate guide to the USA territories’ Caribbean treasure.
Sweeping views and soaring walls
Puerto Rico’s capital, San Juan, is a great starting point to explore the island’s many treasures. And the city itself could keep you occupied for weeks at a time.
Suppose you want to get orientated while also taking in some breathtaking views of the metropolis and its sweeping oceans. In that case, your best bet is to head to Castillo de San Cristóbal. The fort is located in Old San Juan. It was built in 1634 to protect the Spanish from rival European colonizers, desperate to get their grubby hands on the island’s potential riches. The historic citadel is pretty imposing and monumental, standing tall and majestic on 27 acres. Given its size, it’s no surprise that the fort dominates the streets below, and it’s impossible to miss while strolling around Old San Juan.
If you like Piña Coladas……
Piña Coladas were invented in Puerto Rico, and it’s widely believed the cocktail originated in the restaurant and bar, Barrachina. Even if you’re not into creamy, sickly coconut, fruit, and rum concoctions, it’s still worth your time to stop by the historic Old San Juan eatery.
The restaurant’s 200-year-old colonial-style courtyard brims with tropical plants and trees, providing a gloriously shady respite from the heat and the hustle and bustle of the city streets. The interior is equally splendrous, with brightly painted walls, fabulous air conditioning, yummy food, perfectly mixed drinks, and even live flamenco shows several nights a week.
Stroll and shop
If you’re a person who likes to combine your strolling with some shopping, then Calle Fortaleza is the place for you. The colorful cobbled street is lined with fabulous little shops selling wares from local artisans, jewelry, antiques, paintings, clothing, cigars…. the list goes on.
The surrounding area, fringed by the city’s old ancient walls, also provides a plethora of perfect photo ops courtesy of its wealth of beautiful, pastel-colored Spanish-colonial buildings, the flower-packed balconies of Paseo de la Princesa, stunning views of San Juan Bay, the spectacular Santa María Magdalena de Pazzis Cemetery and buzzing busy weekend outdoor market.
Following in Bourdain’s footsteps
Anthony Bourdain was a huge fan of Puerto Rico, for the food as much as the people, culture, and vibe. The late great chef visited the island numerous times, writing multiple articles and filming episodes of his “No Reservations” and “Parts Unknown” hit TV shows.
On one of his trips, Bourdain drove for nearly two hours from San Juan to the tiny barrio of Isabela in Jobos beach. The purpose of his journey soon became apparent after he pulled up a rickety old barstool to a simple wooden counter inside of a dilapidated-looking beach bar.
The decidedly understated eatery, Sonia Rican, had a decidedly limited menu — with just a few choices of freshly caught seafood and fish dishes, ice-cold beers, and mofongo rellenos — a Puerto Rican specialty.
Mofongo is a staple dish of the country, comprised of unripe fried mashed green plantains, mashed garlic, and small pieces of crunchy chicharrón. Mofongo rellenos take it up a notch though, stuffed with either a seafood or shrimp stew, beefsteak, or shredded chicken.
Sonia Rican would likely fail any USA FDA standard health and safety checks, but, hey — Puerto Rico, and double hey —muy muy delicioso.
Puerto Rico is famously lacking in any kind of street signage, and GPS satellite can be sketchy, to say the least. So, when I decided to follow in Bourdain’s footsteps and visit the off-the-beaten-track beach shack, it took me over FIVE hours of driving around and around in circles before eventually finding it.
However, for the record, let me say it was worth every single minute. Perhaps it was the endless driving, boiling heat, mounting frustration, and ever-increasing hunger, but, I swear to god, beer has never tasted so good and been quite so icy cold — and the mofongo rellenos pollos were totally off the charts amazing, for real.
So yeah, just do it.
Totally tropical
Puerto Rico has the only tropical rainforest in the United States (unless I guess you count those shitty Rainforest Cafe theme-restaurants that pollute the mid-west, Vegas and New Jersey with their faux tropical jungle schtick.)
El Yunque National Forest is located a 45-minute drive from San Juan and covers over 28,000 acres of tropical forest, with waterfalls, hiking trails, breathtaking views, picnic areas, swimming holes, rare trees and fauna, birds, coqui frogs, and even Taíno petroglyphs.
Now that beats an order of greasy $15 cheese sticks and a $19.79 “Rainforest Burger” and fries any day of the week.
Get your beach on
Condado is just a ten-minute drive from Old San Juan, but it can feel like a different universe. The seaside strip is a veritable Puerto Rican paradise with the Caribbean sea’s turquoise-colored waves breaking on pristine white sand beaches.
The neighborhood is also packed full of boutique hotels and high-end resorts, cool bars, shops, pulsing clubs, and a slew of eclectic restaurants, including more than its fair (and bizarre) share of Wendy’s.
Fun/useless factoid of the day: Puerto Rico is home to over 70 Wendy’s franchises, spread across the Island, with the majority located in and around San Juan. Think Starbucks in Manhatten, but with crappy square burgers for sale on every street corner instead of iced mocha frappes.
Surf’s up!
Rincon, located on the west coast of Puerto Rico and around a three-hour drive from San Juan, is a surfers’ paradise, with beautiful beaches, incredible waves, good vibes, and even better ocean rides.
Rincon is the perfect locale for every level of surfer, from total beginner to consummate pro. Maria beach is the place for hang ten novices, with many surf schools and teachers available, a gentle rolling break, and no judgment regarding the inevitable (multiple) tumbles that every learner experiences.
Tres Palmas is the sweet spot for seasoned surfers on the other end of the scale, with a sometimes dangerous and deceptive rip tide and swell that can cause waves up to 20ft high. Note to tourists and visiting surfers: Don’t even think about dropping-in; always paddle smart and follow the right of way rules. Ignore the basics of surf etiquette, and shit can get gnarly out there, for real cabrone.
Black & blue
One of the (many) Puerto Rican must-sees is Vieques Island’s bioluminescent bay. The island is around a three-hour drive from San Juan, and it’s home to one of the most beautiful natural phenomenons on earth.
There are numerous excursion trips you can sign up for, or you can go all “Deliverance” style (minus the banjo music and “squeal like a pig, boy!” and hire your own glass-bottom canoe to self-navigate your way through the mangrove channels.
It all happens at night when the stars light up the sky above, and the Caribbean seawater turns inky black before being lit blue by literally millions of spectacular, glowing bioluminescent organisms.
Simply breathtaking.