So what, exactly, is Puerto Rico’s relationship with the United States? You could ask every person you meet and get a different answer -- and a different answer, too, about what Puerto Rico’s future should hold. Should Puerto Rico claim independence and officially incorporate as the 51st state, or continue with its current status as a “free associated state” of the United States? The island’s future is cause for intense debate among its fiercely loyal inhabitants, and they’ll likely be happy to discuss their opinions with you -- Puerto Ricans love talking politics.
Yet more Puerto Ricans live in the continental US than on the island itself. The island’s shrinking population results from an enduring crisis of unemployment and debt, which, while decades in the making, came to a head with the recession and has not yet reached its end. Then came Hurricane Maria, which lashed the island in September 2017, leveling its already-fragile electrical grid and devastating the island’s crops.
Today, parts of the island’s electrical system and roads are still being repaired, and a handful of attractions, including parts of El Yunque National Forest and the Río Camuy Caves, remain closed. Yet the huge majority of the island has bounced back and is eager to welcome visitors. Hurricane Maria, in many ways, left a blank slate for Puerto Rico, and the islanders who remain have seized the opportunity to rebuild, refortify, and reimagine their futures.
When to go: Puerto Rico is beautiful year-round, tropical, rainy, and warm. The high season runs from mid-December through mid-April, when the waves are at their best for surfing, and crowds and hotel rates go up. (TRAVEL TIP: Consider visiting in May when hotels are 10% cheaper than average). Puerto Rico isn’t exactly a budget destination -- hotel taxes range from 7-11%, parking is expensive in San Juan, and gas tends to be costly as well. Since most food is imported, restaurant prices are on par with big cities in the States. You can sometimes score discounted hotel packages during hurricane season (June through November). After Labor Day, flight and hotel prices drop off steeply. September and October have some of the cheapest airfare rates to the island.
Speaking Boricua: You’ll hear plenty of people speak English, and among those speaking Spanish, you’ll hear lots of words that sound like English: wikén (for “weekend”) and parking (pronounced “parkeeng” for, well, “parking”), and more. Boricuas (that is, Puerto Ricans, so named for the original name of the island, Borinquen, given to it by the Taíno) love word play and their Spanish draws from all sorts of cultural and linguistic traditions. One word you definitely need to know? ¡Wepa!, an all-purpose word that could mean everything from “Amazing!” to “Hot damn!” For a fun primer on Puerto Rican Spanish, pick up Jared Romey’s Speaking Boricua before your trip.
Tips on tipping & etiquette: Puerto Ricans are generally pretty laid back and open. "Island time" is a thing here -- in restaurants, expect relaxed service and slow-paced meals. Tip like you would back home (15-20% and a dollar per drink at bars). Pack actual clothes, not just beach cover-ups: people here pride themselves on dressing well, especially in San Juan and the larger cities. Unless you’re actually at the beach or poolside, you shouldn’t be strolling around in your bathing suit.
Getting around: If you think “Puerto Rico” and visions of chicken buses dance through your head, banish those now: Puerto Rico isn’t Costa Rica, and you won’t be careening around perilous mountain curves hanging on for dear life as your nose presses into a fellow passenger’s sweaty armpit (or, yes, their chicken).
Quite the opposite: Cars are king in PR. There are more of them per square mile than anywhere else in the world, and while there are buses and a metro in parts of San Juan, public transportation is neither widespread nor reliable. You can use Uber in the cities, but if you go exploring, rent a car from one of the major rental companies. Don’t skimp on the insurance, and be sure that your plan includes 24/7 roadside assistance. You’ll also need the Puerto Rican equivalent of an EZ-Pass -- peajes, or toll roads, abound, and most of them no longer accept cash.
Driving in Puerto Rico can be, um, adventurous. Be sure to keep your wits -- and your sense of humor -- about you. Gas is sold in liters, and distance is typically (but not always) measured in kilometers… but the speed limit is measured in miles per hour. Signage can be poor, road conditions are hit or miss, and many cars are missing one or more headlights or taillights.
Which is not to discourage you from venturing about. You absolutely should! Far too many visitors fly into San Juan and never leave; sadder still are the cruise passengers who spend mere hours in the Old Town before setting sail again. Tiny but mighty, Puerto Rico runs deep with rural lands and dense jungles, family-run cuchifrito stands and isolated beaches shaded with palms. Thanks to ongoing recovery efforts, these off-the-grid treasures are becoming ever more accessible. Just don't overpack your itinerary -- here, day trips work better as two- or three-day trips. Leave plenty of time to take it all in.