The Caribbean Island has it all: beautiful beaches, an impressive cocktail culture, a tropical rainforest—and you don’t even need a passport.
Puerto Rico Outfits
There’s a lot to do in Puerto Rico, from relaxing on the beach to strolling the cobbled streets of historic Old San Juan to sipping cocktails under the stars. Embrace the tropical vibes of the island by bringing colorful prints, bold hues, and breezy fabrics into your vacation wardrobe. What to wear in Puerto Rico? Here are Caribbean-ready outfits to pack for your holiday in the sun.
1. Tropical Chic
Rio Printed Bandeau Bikini Top
Rio Bow-Detailed Printed Bikini Briefs
2. Easy Breezy
Olympia Oversized Cotton Cropped Top
Formentera Tiered Cotton Maxi Skirt
3. Date Night
Tropicana Asymmetric Midi Dress
Valence Metallic Leather Sandals in Gold
1. From Sightseeing to Swimming
Navy Cuba Terry Shirt
7″ Breaker Stretch Board Short in Golden Sunset
2. Night Out
Rag & Bone
Avery Viscose Printed Shirt
Traveler Pant Stretch Linen Chambray in Khaki
1. Fun in the Sun
Kids’ Garment-Dyed Pocket T-Shirt in Crisp Endive
Kids Bayberry Trunk in Red Tropics
2. Bold Colors & Prints
Smocked Sun Dress-Multi Colourblock
Tropicana Floral Bikini
If you want to explore some of the island’s local beaches, pack eco-friendly bug spray and sturdy shoes.
Top 8 Must Have
Joanna Hat – Honey
Insect Repellent Spray
Woven Straw Market Tote
Calm Movements Eye & Cheek Mask
Women’s Bondi 7
Coffee Run Waterbottle Sling
One Luxe Dri-FIT Stretch Leggings
The Perfect Day
Start the day at Sabrina, a sun-soaked cafe on Calle Loíza serving the usual brunch favorites with a tropical twist plus punchy cocktails. Spend time afterwards strolling the streets of Santuce—the neighborhood is filled with coffee shops, cocktail bars, and boutiques. Don’t miss Moni & Coli for locally-made candles and jewelry, and Nude for sundresses and unique accessories.
Spend the afternoon on the beach. The island has plenty of places to find a perfect patch of sand, including Condado Beach in Santurce not far from the shops of Calle Loiza. The public beach has sun chairs for rent and waiters taking orders for piña coladas, first created in Puerto Rico.
Before dinner, take a walk through the cobblestone streets of Old San Juan and make time to stop in La Factoria for a drink at the world-famous cocktail bar. (Try the Lavender Mule, made with ginger beer and a homemade lavender infusion!) Make a late reservation for dinner at Jose Enrique, where you should order everything on the wildly delicious menu at this local gem.
Kick off the day with a hike through the lush trails and waterfalls of El Yunque National Forest, the only tropical rainforest in America’s National Forest System.
Spend a few hours on Playa Piñones, where you’ll find kiosks with fried conch and cold beers or a drink in a hollowed out coconut. Follow it up with swimming and reading on a nearby secluded beach, like La Pocita or Vacía Talega.
When it’s time for dinner, head for Vianda, helmed by a husband and wife team, and order local produce-infused dishes in low key but lovely environs. Before turning in, schedule an excursion to visit one of Puerto Rico’s bioluminescent bays. Single-celled organisms produce a glowing effect when disturbed. A night time kayak tour is a memorable end to a perfect day.
Fuel up for a day of adventure with fresh coffee and plates of Mallorca—ham and cheese on sweet bread dusted with powdered sugar—at Kasalta, the cafeteria-style island favorite. Afterward make your way to Old San Juan to hike around San Felipe del Morro Castle. The 16th-century fortress offers both a history lesson and prime views of the surrounding skyline.
For a lunch that everyone will love, visit Lote 23. The collection of food trucks and kiosks cater to every taste, with standouts that include mofongo (a local dish made with mashed plantains, shrimp or meat, and sauce), tacos, and ice cream.
In the afternoon, seek out the perfect family-friendly beach. Balneario de Carolina, located on the north shore, is about a 20 minute drive from Old San Juan toward the airport. This beach features calm water, a small waterpark for kids, and restroom facilities.
In the evening, splurge on at Restaurant 1919, inside the Condado Vanderbilt Hotel. The waterfront spot has a menu of carefully-sourced local ingredients and a noteworthy wine list, but it also caters to kids with a special menu and each guest gets some banana bread to-go as you walk out the door.
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