What to Wear in Puerto Rico

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.

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.

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.