Puerto Rico
Puerto Rico is the 100-mile-long island for you if you have a taste for historical sites and cultural calendars filled with spirited events. Most adventures on the “Island of Enchantment” begin in San Juan, the delightful capital with pockets of intrigue on every corner. Night owls should waste no time making a beeline to the hip Santurce neighborhood. Here, you can enjoy street murals, street food, and street parties on breezy nights while sipping piña coladas, Puerto Rico’s gift to the world that was created at the Caribe Hilton hotel in 1954.
Nature lovers and adventurers will want to head to El Yunque National Rainforest to dip in natural pools and spot coqui frogs in the presence of orange-fronted parakeets, yellow-bellied sapsuckers, and red-tailed hawks. Beach bums, meanwhile, will be pleased to know that the island boasts almost 300 beaches, each of which promises sparkling waters and orange-tinted sunsets.
Advertisement
Santa Catalina Island, California
Make like Marilyn Monroe—and a host of other Hollywood notables—and call Santa Catalina your temporary home. Eternally popular for day trips, this laidback island is a hop, skip, and jump from Los Angeles, with ferries regularly departing from Long Beach, San Pedro, and Dana Point. After the hour-long ferry ride, you can explore Catalina's two towns—Avalon and Two Harbors—by bike, golf cart, or foot.
At this Mediterranean-style getaway, water thrills include parasailing, glass bottom boat tours, and expeditions to spot sea lions, dolphins, and whales during their migratory season. On land, you can perch under swaying palms or speed through the sky on a zipline. Or, have a sweet time brunching at Mt Ada, the former home of chewing gum tycoon William Wrigley Jr., who previously owned the island.