The Caribbean Island has it all: beautiful beaches, an impressive cocktail culture, a tropical rainforest—and you don’t even need a passport.

★ Best time to travel: Dec – May

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.

Women

1. Tropical Chic

1. Tropical Chic - Outfit Items
PatBO - Rio Printed Bandeau Bikini Top

PatBO

Rio Printed Bandeau Bikini Top
Shop at Net-a-Porter
PatBO - Rio Bow-Detailed Printed Bikini Briefs

PatBO

Rio Bow-Detailed Printed Bikini Briefs
Shop at Net-a-Porter
Charo Ruiz - Claire Guipure-Lace Cotton-Voile Kaftan

Charo Ruiz

Claire Guipure-Lace Cotton-Voile Kaftan
Shop at MATCHESFASHION
Staud - Women’s Maya Ruched Espadrille Slide Sandals

Staud

Women’s Maya Ruched Espadrille Slide Sandals
Shop at Bloomingdale’s
Bottega Veneta - Cat-Eye Acetate Sunglasses

Bottega Veneta

Cat-Eye Acetate Sunglasses
Shop at Moda Operandi

2. Easy Breezy

2. Easy Breezy - Outfit Items
Ciao Lucia - Olympia Oversized Cotton Cropped Top

Ciao Lucia

Olympia Oversized Cotton Cropped Top
Shop at Moda Operandi
Ciao Lucia - Formentera Tiered Cotton Maxi Skirt

Ciao Lucia

Formentera Tiered Cotton Maxi Skirt
Shop at Moda Operandi
Johanna Ortiz - 24K-Gold-Plated & Mixed-Media Drop Earrings in Flame Orange

Johanna Ortiz

24K-Gold-Plated & Mixed-Media Drop Earrings in Flame Orange
Shop at Saks Fifth Avenue
Binge - Island Bowl Mini Bag in Yellow Hues

Binge

Island Bowl Mini Bag in Yellow Hues
Shop at Shopbop
Larroudé - Helen Flat Sandal in Caramel Leather

Larroudé

Helen Flat Sandal in Caramel Leather
Shop at Larroudé

3. Date Night

3. Date Night - Outfit Items
Zimmermann - Tropicana Asymmetric Midi Dress

Zimmermann

Tropicana Asymmetric Midi Dress
Shop at Mytheresa
Cult Gaia - Valence Metallic Leather Sandals in Gold

Cult Gaia

Valence Metallic Leather Sandals in Gold
Shop at Saks Fifth Avenue
Stella McCartney - The Falabella Vegetarian Brushed-Leather and Raffia Shoulder Bag

Stella McCartney

The Falabella Vegetarian Brushed-Leather and Raffia Shoulder Bag
Shop at Net-a-Porter
J.Crew - Raffia Hoop Earrings in White

J.Crew

Raffia Hoop Earrings in White
Shop at J.Crew
Laura Lombardi - Adriana Recycled Gold-Plated Anklet

Laura Lombardi

Adriana Recycled Gold-Plated Anklet
Shop at Net-a-Porter

Men

1. From Sightseeing to Swimming

1. From Sightseeing to Swimming - Outfit Items
OAS - Navy Cuba Terry Shirt

OAS

Navy Cuba Terry Shirt
Shop at OAS
J.Crew - 7″ Breaker Stretch Board Short in Golden Sunset

J.Crew

7″ Breaker Stretch Board Short in Golden Sunset
Shop at J.Crew
Orvis - Stowaway Packable Panama Hat

Orvis

Stowaway Packable Panama Hat
Shop at Orvis
Mulo - Suede Espadrilles in Beige

Mulo

Suede Espadrilles in Beige
Shop at Mr. Porter
Oliver Peoples - Forman L.A Round-Frame Tortoiseshell Acetate Polarised Sunglasses

Oliver Peoples

Forman L.A Round-Frame Tortoiseshell Acetate Polarised Sunglasses
Shop at Mr. Porter

2. Night Out

2. Night Out - Outfit Items
Rag & Bone - Avery Viscose Printed Shirt

Rag & Bone

Avery Viscose Printed Shirt
Shop at Rag & Bone
Onia - Traveler Pant Stretch Linen Chambray in Khaki

Onia

Traveler Pant Stretch Linen Chambray in Khaki
Shop at Onia
Mr P. - David Suede Sandals in Dark Brown

Mr P.

David Suede Sandals in Dark Brown
Shop at Mr. Porter
Warby Parker - Robbie Polished Gold

Warby Parker

Robbie Polished Gold
Shop at Warby Parker
Marathon Watch Company - Navigator Watch in Sage Green

Marathon Watch Company

Navigator Watch in Sage Green
Shop at J.Crew

Kids

1. Fun in the Sun

1. Fun in the Sun - Outfit Items
J.Crew - Kids’ Garment-Dyed Pocket T-Shirt in Crisp Endive

J.Crew

Kids’ Garment-Dyed Pocket T-Shirt in Crisp Endive
Shop at J.Crew
Fair Harbor - Kids Bayberry Trunk in Red Tropics

Fair Harbor

Kids Bayberry Trunk in Red Tropics
Shop at Fair Harbor
Janie and Jack - Braided Straw Fedora

Janie and Jack

Braided Straw Fedora
Shop at Janie and Jack
Sea Star Beachwear - Beachcomber Espadrille, Dark Navy

Sea Star Beachwear

Beachcomber Espadrille, Dark Navy
Shop at Maisonette
Gap - Kids Recycled Sunglasses in Clear

Gap

Kids Recycled Sunglasses in Clear
Shop at Gap

2. Bold Colors & Prints

2. Bold Colors & Prints - Outfit Items
Boden - Smocked Sun Dress-Multi Colourblock

Boden

Smocked Sun Dress-Multi Colourblock
Shop at Boden
Zimmermann Kids - Tropicana Floral Bikini

Zimmermann Kids

Tropicana Floral Bikini
Shop at Mytheresa
Janie and Jack - Crochet Straw Sun Hat

Janie and Jack

Crochet Straw Sun Hat
Shop at Janie and Jack
Sam Edelman - Vita Kids Braided Sandal in Lt Cuoio Brown Leather

Sam Edelman

Vita Kids Braided Sandal in Lt Cuoio Brown Leather
Shop at Sam Edelman
My Little Sunnies - Round Vintage Sunglasses, Pink

My Little Sunnies

Round Vintage Sunglasses, Pink
Shop at Maisonette

Pro Tip

😎

If you want to explore some of the island’s local beaches, pack eco-friendly bug spray and sturdy shoes.

The Perfect Day

Girls Trip

MORNING

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.

DAY

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.

EVENING

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.

Romantic Getaway

MORNING

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.

DAY

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.

EVENING

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.

 

Family Trip

MORNING

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.

DAY

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.

EVENING

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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