San Juan, Puerto Rico’s capital, is a city where cobblestone streets lead to centuries-old forts and pastel-colored buildings overlook the Atlantic. The district of Old San Juan is a UNESCO World Heritage Site, known for its Spanish colonial architecture and thick stone walls that once defended the city from pirates and naval attacks. The city hosts regular events such as La Campechada, which celebrates Puerto Rican art and literature with live performances and open-air exhibits.

Vieques Island is found in the northeastern Caribbean, roughly 8 miles east of the Puerto Rican mainland. Its beaches are commonly acknowledged as some of the Caribbean's best. The Bioluminescent Bay is especially alluring given the undeveloped nature of the island.