Puerto Rico has all the makings of a fantastic tropical getaway — beaches galore, snorkeling and scuba diving right off the coast, plus a hot dining scene with lots of cultural influences and a vibrant nightlife — but there are a few things that push this Spanish-speaking destination into bucket-list territory.
It may be only 100 miles long and 35 miles wide (a three-hour drive from east to west), but you’ll find the world’s most beautiful bioluminescent bays (including one you can swim in), an island where horses roam free and a historic district lined in colorful homes and grounded in iconic blue cobblestones.
As always, check for travel restrictions and closures before planning your trip.
Friday: Visit the Iconic Sites of San Juan
Most travelers start and end their trip in the metropolitan section of the island, where San Juan, the capital of this U.S. territory, is found. This is a great area to get your bearings and start to dip your toe into this rich, vibrant destination and its Latinx culture.
Pick up breakfast from Spiga, where the bread is made fresh daily, and grab your coffee from Finca Cialitos — the coffee beans are grown locally on the owner’s land. It’s a great opportunity to taste Puerto Rico’s terroir.
Finca Cialitos puts you steps away from the San Juan National Historic Site, which includes Castillo San Felipe del Morro — better known as El Morro — and Castillo San Cristóbal, which was built by the Spanish to protect the island from impending attacks on land.
You can book a guided tour with a local operator or explore the area on your own. Don’t miss the old walls, which protected the island’s fort, castle and riches. Climb to the top of Castillo San Felipe del Morro for stunning views of the San Juan Bay and spend some time taking in the San Juan Gate.
All of those steps will build up an appetite, so listen to your stomach’s cue and get ready for the island’s most treasured local dishes, including mofongo, deep-fried green plantains; tostones, double-deep-fried plantain wheels; and lechón, a spit-roasted pork dish.
Comida criolla is a Puerto Rican cuisine that blends local ingredients used by the Taino Indigenous people with Spanish and African influences, and it’s best experienced at Deaverdura. The menu is heavy on the meats, but the staff is always willing to accommodate vegan or vegetarian requests.
Part of San Juan’s charm is its walkability. Allow yourself time to roam the streets and really admire the colorful scenery as you move from place to place. As the sun sets, start the night at Antiguo 26, a Prohibition-themed eatery serving up ceviche and steak.
From there, pop in to Casa de Montecristo for a post-dinner cocktail. The cigar lounge boasts some of the best mixologists in the city. The Wanderlust — made with Montelobos mezcal, Campari, lime and passion-fruit foam — is one of several dreamy cocktails on the bar menu.
Saturday: Wind Down and Relax in Vieques
Head to Vieques for your second day in Puerto Rico, an island 7 miles off the coast. This destination is a beloved getaway destination for locals: The small island is only accessible by ferry or small plane. But first, breakfast: Head to Café Playero in Fajardo, a 55-minute drive east from San Juan, a restaurant lauded for its home fries and huevos rancheros.
From there, you’re water-bound. You can catch a 30-minute ferry to Vieques from Ceiba — a 20-minute drive south from your breakfast stop — aboard the Puerto Rico Fast Ferry. Once you’re back on land, a number of secluded beaches can be found in the Vieques National Wildlife Refuge.
If napping on the beach isn’t quite your speed, hike to Playa Negra, a black-sand beach surrounded by the ruins of the Playa Grande Sugar Plantation. There are no restaurants or vendors within the refuge, so be sure to pack a hearty lunch, or simply visit one of the food trucks located outside its limits.
If you want to see another side of the island, head to Mosquito Bay — the brightest bioluminescent bay in the world — for snorkeling during the day. You can also kayak around the bay at night to see its glow in action. Hurricane Maria damaged the area and disturbed the microorganisms, but they have thankfully since made a return.
Fill up at Coqui Fire Café for an early dinner alfresco in downtown Isabel Segunda. The last ferry leaves for the mainland at 8 p.m., so don’t miss it. If you’ve got some time to kill after dinner, grab a namesake drink at Bilí, made with rum and fermented Spanish lime.
After your quick boat ride back to Ceiba, make the drive to the Condado neighborhood for a different side of Puerto Rico’s nightlife. This ritziest neighborhood in Puerto Rico is home to a ton of cocktail bars and rooftop lounges.
Start at the Bar.C.Lona Rooftop bar at the AC Hotel and barhop until the party starts at Kali, a late-night tapas spot and lounge that doesn’t really get going until the wee hours of the morning.
Sunday: Gear Up for a Day of Exploration and Adventure
Start your morning at Café Mimosa in San Juan. Known for its — you guessed it! — mimosas, this breakfast restaurant covers the classics: French toast, breakfast sandwiches, yogurt parfaits and a separate frittata menu will fuel you up for the adventures to come.
For a quieter scene, make your way to Toro Verde Nature Adventure Park. This eco-park is nestled in the mountains of Orocovis, a town in the central mountain range that’s considered by locals to be the heart of the island. Heads up: Toro Verde is an hourlong drive from San Juan, but experiencing this contrasting environment is completely worth the time on the road.
If you’re looking for an adrenaline rush, you’ll be happy to learn that it’s also the largest aerial park in the Western Hemisphere, with miles of zip lines. If flying over the treetops isn’t your idea of fun, you can also hike the park’s mountainous trails or take a ride on a world-class mountain-bike trail on Marla Streb’s Singletrack Jungle, an adventure camp.
On your drive back toward San Juan, stop in Bayamón — about an hour away from the park — for lunch at Doña Ana. This spot’s self description is all you need to hear to get you in a seat: Your Puerto Rican aunts’ and grandmothers’ restaurant.
You may have guessed, but it serves up some can’t-miss traditional fare. After the bill is paid, pick up a piragua, or sno-cone, for dessert from one of the surrounding street vendors. And if any of the fútbol teams have matches on the schedule, consider sticking around for a game: Cheering on the home team is what Bayamón is known for and where you can find most locals on game day.
If all the teams are away, make your way back to San Juan for a hot shower and a poolside nap.
After freshening up, head to Vianda for dinner. The restaurant features a rotating cast of local chefs for a vegetable- and seafood-inspired menu featuring island-sourced ingredients. You could call it a night, but we recommend living it up like a local and heading to La Placita de Santurce for your last night in Puerto Rico.
This 100-year-old marketplace transforms from an outpost selling meats, fruits and vegetables during the day to a meeting spot for drinks and salsa dancing once the sun sets.
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