Pristine beaches and intoxicating jungles. Incredible food. Centuries’ worth of history and culture. No passport required for US citizens. The only drawback to visiting Puerto Rico is that if you’ve never been, you’ll be kicking yourself on that first trip for not visiting sooner. It’s remarkable how often we forget that San Juan is a stunner of a destination, with its vibrant neighborhoods, street art, and joie de’ vivre that’s extended to locals and tourists alike. It’s also incredible to think that this city has been standing since long before the Mayflower found its way to Plymouth Rock; San Juan was founded in the mid-1500s. The city’s enduring spirit is matched in magnitude by its exquisite surroundings, and the ease of actually getting there makes it a no-brainer for a beach escape. San Juan’s past is really something – but there’s no time like the present to see it for yourself.
History buffs, family trips, romantic getaways, rambunctious group outings, anyone seeking a warm-weather escape in the depths of winter
You might think that San Juan is an inexpensive place to visit – after all, it’s on a small island in the Caribbean, where plenty of beach getaways can be had on the cheap. In truth, it’s not terribly expensive, but it isn’t terribly inexpensive, either. Hotel rooms in the city are reliably priced between $150 and $300 nightly, with beachfront properties running up to $400 a night. Food and drink, however, are a fair bit cheaper than what you’d expect in other US tourist destinations, ranging from $10 to $35 on the more deluxe end of the market.
The tourism industry is a huge part of the local economy in San Juan, and as such, keeping tourists safe is a top priority. You can expect to feel safe in San Juan regardless of gender or sexual orientation – the island is known as a great destination for the LGBTQIA+ community – though BIPOC travelers may sense some racism in pockets of the city and island at large. While incidents of crime are rare, police officers are often bilingual.
Puerto Rico’s tropical climate means visitors are treated to warm and sunny weather almost year-round. The seasons, then, are more distinguished by rainfall than anything else.
Winter in San Juan, from mid-December through about mid-April, is when the weather is most warm, welcoming, and dry. Hurricane season runs from June through November, and it’s when San Juan (and the rest of Puerto Rico) is at its wettest and hottest.
Winter is San Juan’s high season, as travelers come to escape colder climates in the northern hemisphere, so the best weather also means the biggest crowds and highest prices on things like hotel rooms.
Despite its mostly consistent year-round temperatures, San Juan does have shoulder seasons, which can be a good option for budget travelers. The temperatures from April through June climb steadily toward hurricane season, but most of the crowds have gone home.
Hop on the free trolley. There are two trolley routes through Old San Juan that are completely free and stop at many of the popular attractions. Note that they can be extremely crowded when a cruise ship’s passengers are exploring the town.
Eat like the locals. Skip the hotel and resort restaurants and seek out eateries away from the more popular tourist areas. You’ll likely find more locals eating there, where prices are lower.
Rent a car for island excursions. While getting around in the city using public transportation, taxis, or rideshares is less stressful, getting out of the city on day trips with a rental car is more budget-friendly.
Foodies rejoice! Puerto Rico is full of flavor and creativity, meaning you’ll be spoilt for choice when it comes to your next meal. In San Juan, the old and the new can sometimes clash – but they live in harmony on where food is concerned, with farm-to-table eateries and hipster bars serving as a complement, not an opponent, of traditional flavors; likewise, pub fare and high-end dining are both in ample supply. Don't miss mofongo, one of the island's most popular dishes. Then there’s the rum, wherein words fail, so we’ll leave you with just three: Ron del Barrilito.
The main question when deciding where to stay in San Juan can be boiled down to this: Beach or city? There are benefits to both, so the choice usually has more to do with where you plan to spend most of your time. With both options, you’ll have your pick of hotels in all price ranges, from budget hotels to the resorts that proliferate on the coast. Even budget hotels, however, often cost about $100 per night.
Old San Juan is the most popular place to stay in the city, by a long shot – after all, it’s home to many a historic fortress, those famous 15-foot-thick walls are a sight to behold, and, since it’s so tourism-saturated, you won’t stick out here.
That said, you’d do well to check out Santurce and Isla Verde. The former is a colorful, culture-loving neighborhood, home to a formidable array of museums, shops, galleries, restaurants, and street art – plus the oceanfront Condado area, an upscale strip of resorts, pools, and swimming holes. The latter is a bit east of San Juan proper and is known for being a lively playground of water sports and nightlife, with plenty of accommodations to go around. Inland Santurce is the most budget-friendly – under $200/night, but with few options – while Condado and Isla Verde cater to a higher price point, with most places between $250 and $400.
Deciding on a mode of transit in San Juan is a literal choose-your-own-adventure sort of endeavor, and there are no wrong ways to go about it. Uber and taxi cabs are easy to hail in the city, the light rail is reliable, and the buses aren’t half bad (though traffic very well may be). When it comes to the rest of Puerto Rico, there are shuttles and tour buses if you aren’t keen on driving, but exploring the island in a rental car is a great way to have a more intimate, authentic experience as you traverse, and the roads, while winding, are in good shape.
The main airport in Puerto Rico is Luis Muñoz Marín International Airport (SJU), located a short three miles from San Juan. It’s a hub for Air Sunshine and some charter airlines, and a focus city for JetBlue and Silver Airways.
While rideshare companies Uber and Jaime te lleva (a local app) make it easier to get around once you’re in San Juan, they don’t serve the airport. To get from Luis Muñoz Marín International Airport into the city, there are metered taxis that have fixed fares (starting from $12) depending on where you’re going. The drive takes about 15 minutes. There are also public bus lines that connect to the airport, but luggage isn’t allowed on any of them. If you’re staying at a hotel or resort, they may have a dedicated airport shuttle.
Puerto Rico has often served as the stand-in for films set in other places. In Amistad, El Morro in Old San Juan was a 19th-century Sierra Leone. In Bad Boys II, the northern coast became Cuba. In Fast Five, San Juan and Naranjito were turned into Brazil. Pirates of the Caribbean: On Stranger Tides used filming locations all over the island.
Hunter S. Thompson's book The Rum Diary takes place in 1950s San Juan, and it was later turned into a movie filmed in the city. The Puerto Rican Pearl is a mystery novel by J.A. Jernay, and Rosario Ferré’s The House on the Lagoon ties one family’s history to the history of Puerto Rico.
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