What to See and What to Skip in San Juan, Puerto Rico

PHOTO: Aerial view of Old San Juan cityscape and beach, Puerto Rico, in this undated photo.Getty Images
Aerial view of Old San Juan cityscape and beach, Puerto Rico, in this undated photo.

Puerto Rico’s appeal as a Caribbean hot spot remains strong: it was named the #1 U.S. island in USA Today’s 2016 Readers’ Choice list.

Easy access has a lot to do with that, as well as the ease of travel since Puerto Rico is a U.S. territory (no passport required!).

Then there’s the cuisine, culture and fascinating history.

The capital city of San Juan sees the vast majority of arrivals, both by plane and by cruise ship. While San Juan is a threshold to myriad destinations within Puerto Rico well worth discovering, it’s also an attraction all its own.

Here are a few special things to do in San Juan:

Pay Two Nights, Stay Four
There’s a big push to attract visitors in 2016: more than 20 of the top hotels across Puerto Rico are offering an unprecedented “buy two nights, get two nights free” deal. Several of those hotels are in San Juan, including the 4-Star Condado Plaza Hilton (where four nights start at $498), the swanky San Juan Water & Beach Club (four nights from $358) and the upscale Sheraton Old San Juan Hotel (four nights from just $218). You’ll find the full list on the Travelzoo website, with travel options through mid-December.

Skip Winter, Visit Summer
By late December, Puerto Rico hotel rates begin to soar, driven by the year’s best weather and strong traveler demand. For bargain hunters, it’s all about summer. The July-through-September off-season brings the threat of stormier weather, but with rates slashed by 50% to 75%, it can be a real boon for your pocketbook. Fall, with milder weather, can also generate airfare and hotel bargains.

Skip Breakfast, Hit the Sand
San Juan’s beaches are a big draw, but if you want to avoid the crowds – from locals to hotel guests to cruising day trippers who’ve just disembarked – get there early. Mornings (as well as late afternoons) offer the same gorgeous views and temperate waters but with plenty more elbow room. Try the sands of Carolina Beach, Ocean Park Beach and Condado Beach.

Celebrate NPS, Visit El Morro
A visit to Puerto Rico’s capital is a chance to celebrate the 100th birthday of the National Park Service. San Juan is a National Historic Site – a haven cradling more than 500 years of history. For most of that time, San Juan was a strategic stronghold for the Spaniards and, today, visitors can walk along preserved old city walls and visit legendary landmarks like Castillo San Felipe del Morro (known simply as El Morro), Castillo San Cristobal, the San Juan Gate and Fort San Juan de la Cruz. The entrance fee is $5 and doors are open daily, except for a few major holidays.

Take a Break, Fly a Kite
History aside, El Morro is extremely popular with kite flyers. The conditions are ideal: wide open space, no obstructions overhead and dependable trade winds. Several onsite vendors will sell you a kite –- just ask for a “chiringa.”

Skip the New, Tour the Old
Paying a visit to Old San Juan, with its cobblestone streets, pretty plazas and colorful colonial buildings, is a must. Hilary Solan, a website editor at Travelzoo’s Chicago office, visited San Juan for the first time recently “and all my favorite places were in Old San Juan!” she said. “Across the street from the Cathedral of San Juan Bautista is the small Hotel El Convento, a perfectly preserved luxury hotel. Once a monastery, the property still has its Andalusian tile floors and hacienda-style furniture. I wasn't able to stay there on my last visit, but I did grab a leisurely lunch and a cocktail in the first-floor open-air restaurant and vowed to stay there on my return visit.” Solan also recommends cruising the shops and eateries along popular Fortaleza Street, where she got fitted for a Panama hat at a store called Olé. “In the tiny storefront, there are about a dozen styles and after that, you pick the color and the ribbon,” she recalls. “It's the perfect, customized souvenir!” There are several companies, like Old San Juan Heritage Walking Tours, that offer insightful guided walks through this very special part of town.

Skip the Cab, Rent a Bike
The folks at Rent the Bicycle offer a 90-minute tour of Old San Juan on two wheels, and they’ll also customize guided bike treks throughout San Juan. But this is also a great option for visitors who like to discover solo: rent your own bicycle for $27 a day, helmet included. Child seats are available for kids under 36 pounds.

Skip the Streets, Sail the Bay
It’s easy to just stare out at beautiful San Juan Bay, but this estuary –- teeming with coral, underwater forests and seagrass beds -– is well worth experiencing. Anne Reardon, a senior associate producer in Travelzoo’s Chicago office, highly recommends chartering a boat for the day, which can be arranged through your hotel. “When I went, we had a 30-foot boat with a private captain, so we could go anywhere we wanted,” she says. “The captain took us to a coral reef where we snorkeled, and then we boated over to other smaller islands for lunch. The captain provided food and drinks on the boat, so all we did was show up. It was our favorite day of the entire trip.” There are several great companies to choose from, like Sail San Juan Bay, which caps groups at six and uses a slick J30 racer/cruiser sailboat.

Skip the Restaurant, Do the Tour
The food in San Juan is some of the most delectable island fare in all of the Caribbean. It is an attraction all its own and the establishments here help define many of the colorful neighborhoods they’re in. For foodies, customizable tour options abound here. Family-run Spoon Food Tours, for example, offers several guided culinary excursions that combine lessons on the history and architecture of the areas you visit. They offer family-friendly tours in English, both in the mornings and the afternoons. Check out their Sip & Savor Drinking Tour, which features tastes of a bevy of rum-inspired concoctions.

Skip the Bar, Tour Bacardi
The famous Bacardi brand arrived in Puerto Rico in the 1930s. Today, its San Juan facility bottles millions of cases of rum for international export while remaining a stop for many a thirsty visitor. Bacardi offers three tours daily, including a historical tour of the company and a tasting tour of myriad signature rums. The Mixology Tour will run you $45 and includes access to their Cathedral of Rum, hands-on lessons on several Bacardi cocktails and even an official Certificate of Completion.

Skip Dessert, Visit Casa Cortes
The family-owned Casa Cortes Chocobar in Old San Juan serves breakfast, lunch and dinner – and chocolate, as this eatery’s name implies, features prominently in most menu items. Baguette stuffed with brie and chocolate, anyone? This is also a great spot to sit back and relax over a bevy of chocolate dessert items – from mousses to cakes to hot chocolate – before you head upstairs to the free art gallery that features the Cortes family’s extensive collection. The Chocobar features weekly menu specials and two-for-one cocktails during Friday evening happy hour.

Skip Stargazing, Visit the Observatory
Puerto Rico houses to the world’s largest single-dish radio telescope. Spanning some 20 acres and capable of predicting when and where asteroids will hit Earth, it operates 24 hours a day and feeds data to scientists all over the world. The Arecibo Observatory can make a neat family-friendly day-trip, with a visitor center that features 3500-square-feet of planetary exhibits, a science store and an observation platform that offers sweeping views of the 1000-foot telescope. Arecibo is about 50 miles west of San Juan. Head out on your own (admission is $12 for adults, $8 for kids and seniors) or contact any of the several tour companies that will pick you up at your hotel and also include a tour of the famous Camuy Caves that are nearby.

Gabe Saglie is Senior Editor for Travelzoo, which features exclusive deals to and in Puerto Rico. Any opinions expressed in this column are solely those of the author.

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