From old city to revitalized coast
The Caribbean jewel of Puerto Rico has long embodied a double life as the best-preserved Spanish colonial city in the world in Old San Juan and a major pharmaceutical manufacturing center via 2,000 commercial plants around the island. Puerto Rico is an exotic tropical resort escape and a U.S. territory with a bustling urban center.
Meet and Stay
My home base during my latest sojourn was the renovated El Conquistador Resort, the island’s largest event campus, where 100,000 sq. ft. of meeting and event space flow into 750 guest rooms and a central lobby and pool area with spectacular ocean views. A funicular transports guests to a marina level where private boats delivers lucky visitors to Palomino, a private island for catered events.
Another exclusive northeastern escape is Hyatt Regency Grand Reserve Puerto Rico, where a multimillion-dollar investment turned Gran Malia Hotel into a sophisticated oceanfront haven on 72 acres. The 579 rooms are largely suites collected into bungalows. Behind gated limestone entrances, Regency Suites offer private plunge pools and spa bathrooms. A 12,000-square-foot rainforest spa boasts indoor and outdoor treatment rooms, a 24-hour fitness center, tennis courts and a basketball court. Two world-class, Tom Kite-designed 18-hole championship golf courses host the PGA Puerto Rico Open. Water sports, including kayaking and stand-up paddleboarding from the ocean beach, offer options beyond the collection of swimming pools.
Fairmont El San Juan Hotel, minutes from the airport on Isla Verde Beach with 30,000 sq. ft. of chandeliered meeting space, is fresh off a $65 million redesign that preserved the historic Morris Lapidus mid-century luxury. The property is an oasis of 388 guest room suites, restaurants, bars and lounges, Well & Being Spa, tri-level fitness center and the newly opened Foxwoods El San Juan Casino. Rose Carrera marble from Tuscany, tapestries from rural France and cherry mahogany from Santo Domingo carved by 16 local craftsmen to form the arched ceilings set the foundation that still stands today. The Palm Court Lobby’s hand-blown Czechoslovakian oval chandelier weighs in at 4,000 pounds.
Nearby, The Ritz-Carlton, San Juan announced that it will reopen in mid-2025 after $150 million in upgrades, including a new suite that brings the total guest room count to 417 rooms.
The original ultra-luxury hotel, Condado Vanderbilt, leveraged its prime location on the Atlantic and attention to detail in the decor and service to attract the rich, famous and connected in 1919. Nearly 200 years and two tower additions later, the luxurious guest rooms still come with Five Diamond butler service. The location in the midst of shops and restaurants, water sports and views makes it a first-class urban resort. A Michelin restaurant, cigar and champagne bars have turned it into a bleisure magnet.
Down the street, La Concha Renaissance San Juan Resort stands out as a shell-shaped retreat with 478 guest rooms, award-winning lounges, restaurants and meeting space.
San Juan’s Convention District is a treasure trove of vibrant meeting spaces. Puerto Rico Convention Center boasts 600,000 sq. ft. of meeting space with one of the most advanced AV and high-speed broadband connections anywhere. Nearby, Sheraton Puerto Rico Resort & Casino is convention headquarters with 503 renovated guest rooms and a sun deck rooftop.
Nearby, entertainment district Distrito T-Mobile is the hotspot for dining, shopping and zip lining. This is also the home of Coca-Cola Music Hall and Aloft San Juan.
Do
Patria Tours takes visitors through Old San Juan to another time via blue cobblestone streets that date back to the 1500s. A popular spot is La Factoria, a speakeasy collection of six lounges voted the best in the Caribbean and available for cocktail-making team building.
Across from the historic Catedral Basilica de San Juan Bautista is El Convento, a former convent that preserves the stately woodwork, art and fixtures of the 16th century. The lush Spanish courtyard at the center is now home to an elevated restaurant/bar, and the rooms have all the modern conveniences, including plenty of outlets for electronics. A sister property, Palacio Provincial, also includes a rooftop pool deck with San Juan Bay views.
This article appears in the January/February 2025 issue. You can subscribe to the magazine here.
