48 Hours in San Juan

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The plain of clouds extended before us: an infinite white sheet, soft and glowing with possibility. We had escaped the world and its limitations, for at least a weekend. It was February, and we were flying to Puerto Rico.



The Lobby of the Swanky Condado Vanderbilt Hotel

San Juan’s Condado Beach area is your most efficient path to the vacation essentials of sun, sand, and surf. It is a fifteen-minute taxi drive from the San Juan Luis Muñoz international airport, and there are numerous beachfront hotels with gorgeous views.

Our pick is the luxurious Condado Vanderbilt Hotel, originally built in 1919.  This grand dame has welcomed notable clients including Charles Lindberg, Bob Hope, and President Franklin D. and Eleanor Roosevelt. The hotel will not disclose the identities of more recent celebrity guests. The Vanderbilt is fully restored and boasts a gorgeous lobby, cigar lounge and oceanfront terrace that is perfect for socializing with a cocktail before a night on the town. Guests who opt for a suite receive personal butler services for the length of their stay.

Condado Vanderbilt Hotel: 1055 Ashford Avenue, San Juan 00907, Puerto Rico



Orozco’s Serves Up Authentic and Tasty Puerto Rican Food

Authentic Puerto Rican cuisine is delicious and inexpensive, and you can find a selection of island meal staples at the very casual, friendly, and excellent Orozco’s on Ashford Avenue. Mofongo is a traditional Puerto Rican delicacy made from mashed plantains and garlic, fried, and usually served with meat or seafood and a savory sauce.  You can have your mofongo with green or ripe plantains; the latter is sweeter but we prefer the green. Try both and be your own judge. Tender roast pork, or pernil, is another island specialty. A side of rice and beans or rice with pigeon peas (arroz con gondules) rounds out any meal. 

Orozco’s: 1126 Ashford Avenue, San Juan, 00907, Puerto Rico (open for breakfast, lunch and dinner)



Memorable Wine Flights at Marmalade Restaurant

Marmalade restaurant provides the type of dining experience that you will remember for the rest of your life. In addition to creative and delectable food, the wine list is spectacular.  Opt for wine pairings on the four, five, or six course tasting menu, all of which are a tremendous value for the quality, artistry, and sheer enjoyment of the meal.  Despite the elevated dining experience, the chef and staff keep the atmosphere friendly and completely unpretentious. In fact, when we visited (on two separate occasions), Chef Peter came out and spoke personally with every single table in the house. The Tuscan White Bean Soup, a house specialty, is not to be missed. (Note: If you can’t get in to Marmalade, Inarü restaurant in Old San Juan is another excellent choice.)

Marmalade: 317 Calle Fortaleza, San Juan, 00901, Puerto Rico



“La Placita” Hosts San Juan’s Hottest Block Party

Our top recommendation for what to do in San Juan is a jaunt to La Placita de Santurce on a Thursday, Friday or Saturday night. This is where locals converge to people-watch, enjoy inexpensive drinks and most importantly, to dance salsa. Bars line the streets of the plaza, which is cordoned off from traffic by the police on party nights. The scene is packed with Puerto Ricans of all ages, showing off their hottest dance moves. You will have to experience this epic, authentic street party to believe it: it’s not for tourists. Ask your hotel concierge for directions.


Safe Swimming at the Sheltered Playita Del Condado

Though beautiful, the waves at Condado Beach proper can get choppy and downright dangerous for swimming, and undertow can be an issue. For a calmer experience well suited to snorkeling or floating, head to Playita del Condado, a sheltered swimming cove off of Ashford Avenue, at the western end of the Condado resort area. Rent a kayak or paddleboard here and cool off with a refreshing shaved ice from a local street vendor.



El Batey’s Bar in Old San Juan, for Rum and Reflection

For a quick change of pace from the Condado resort district, take an Uber to Old San Juan. With its rows of sherbert-colored facades, quaint shops and cafes, and cobblestone streets, it is a wanderer’s paradise. Meander in and out of old churches, or take in a street performance in one of the many town squares. Stop into a dive bar such as El Batey’s, and start planning your next trip back to the island.

El Batey: 101 Calle del Cristo, San Juan, 00901, Puerto Rico




Yasmin Rahim is a strategic communications consultant and freelance writer living near Washington, D.C. Her interests include luxury travel, clean eating/gluten-free cuisine, holistic healing and wellness, and arts/culture.

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