San Juan's Luxurious Beachfront Neighborhood Is Called 'The Manhattan Of The Caribbean'

One of Puerto Rico's best cities for enjoying a sublime winter vacation, San Juan is a mosaic of colorful neighborhoods, with a little something for everyone. History buffs may gravitate to Old San Juan, with its centuries-old cobblestone streets winding past historic citadels and the Catedral de San Juan Bautista, the second-oldest cathedral in the entire western hemisphere. But those with a penchant for the sleek and chic should head to Condado, which lies on its own glorious peninsula just north of downtown San Juan.

Condado is often referred to as the "Manhattan of the Caribbean," according to luxury real estate companies like Apex Luxury Realty and the Corcoran Group.  The moniker pays homage to the enclave's urban sophistication and exclusivity, due to its small size. At only 200 acres, Condado is a tiny neighborhood, even by island standards. Yet, its grandeur knows no bounds.

While Condado may lack the Old World charm of San Juan's most historic districts,  it's definitely the place to be in Puerto Rico if you enjoy the finer things in life. Remarkably distinct from Old San Juan's pastel-colored historic houses, Condado's tall high-rise condos tower over modern streets and golden-sand beaches, giving way to the turquoise waters of the Caribbean. Lined with upscale boutiques, eateries, and nightclubs, the neighborhood's main commercial thoroughfare, Ashford Avenue, is the island's take on Manhattan's posh 5th Avenue. Those with deeper pockets — whether they're seasonal visitors or long-term residents — won't run out of things to do around here, from strolling along the beach and lounging at the pool to dabbling in the high-end real-estate market. 

Condado has been synonymous with luxury since the early 1900s, when well-heeled entrepreneurs like Sosthenes and Hernand Behn and Frederick William Vanderbilt flocked to the area, lured by the sparkle of development opportunities around Condado Beach just a few whaletail lengths (2.7 miles to be exact) from Old San Juan. Today, the area is one of the island's most sought-after real estate markets, where a five-bedroom penthouse condo on Ashford Avenue will set you back a cool $22 million. Included in that price are not just the 10,000+ square feet of living space, bordered by wide glass walls with panoramic views of the ocean, but also use of the building's plush theater room, state-of-the-art wellness center, and 75-foot-long infinity pool.

Those without a proclivity for high-end real estate investments can also partake in the luxurious lifestyle that Condado offers, even if just for a long weekend. For example, an overnight stay in a standard room at the stately Condado Vanderbilt Hotel — where  Charles Lindbergh, Bob Hope, and Presidents Franklin Delano Roosevelt and John F. Kennedy once rested their heads — is between $400 and $1,000 per night during the winter high season. Even a standard room at the hotel promises a luxury experience, with 300-thread-count Rivoita Carmignani linens and spa-like bathrooms. But of course, the property also offers 100 different suites for those seeking the utmost in Caribbean opulence, including amenities like wet bars, butler service, exquisite dining areas, and more. These include the Presidential Suites, which sit on top of the hotel's towers and run upwards of $5,000 per night in high season.

Many a Puerto Rico tropical beach is like a postcard come to life, and with its golden sands and waving coconut palms, Condado Beach is no exception. Though this urban beach isn't exactly secluded, it's a superb spot for lounging in the sun, listening to music, and just general people watching. Young and less experienced swimmers should take care, however, due to the potentially strong currents and big waves that are notorious at this particular beach. 

Beyond beachgoing, popular activities around Condado include browsing the luxury boutiques along Ashford Avenue and at the nearby Mall of San Juan, where shoppers can find brand-name products from Cartier, Louis Vuitton, Gucci, and Salvatore Ferragamo, along with collections by local designers like Nono Maldonado and Harry Robles. The dining scene is nothing to sneeze at, either, boasting a range of eateries from casual-chic oceanfront cafes serving fresh Puerto Rican fare to exquisite formal fine-dining venues like the Condado Vanderbilt's 1919 Restaurant, named after the year that the hotel was opened. 

Condado is conveniently located only 5 miles from San Juan Airport (SJU), also known as the Luis Muñoz Marin International Airport, which is the main aviation hub on the island. If you aren't renting a car, the best way to reach Condado from the airport is to take an Uber, a taxi, or the San Juan Airport Shuttle. The Condado neighborhood is compact and pleasantly walkable, so you won't need a car to navigate this particular neighborhood. However, if you're venturing out to explore rural areas, remote beaches, or the mountains, a rented vehicle will allow for maximum convenience and flexibility.