8: San Juan, Puerto Rico
Didn’t expect to see the Puerto Rican capital on the list? Think again: The culinary capital of the Caribbean boasts trendy bars, lively flea markets, and a tech-savvy population. Hipster Neighborhood: Old San Juan creative commons/vxla
Cementario Santa Maria Magdalena de Pazzis (FLICKR/vxla)

San Juan is a city steeped in myth and tropic fantasy. It's a place where crystal clear Caribbean water meets cool cobblestone streets. Be it the old world, aromatic alleyways of Viejo San Juan, the young, collegiate energy of Rio Piedras, or the ultra-modern strip of Condado, the city is nothing like you may expect.

It's better!

The sun is relentless, the rum endless, and the night is as wild as the day. Some say New York is the city that never sleeps, but they've never been to San Juan.

San Juan packs in more historic monuments, museums, cafes, bars and beaches than any other city its size. A weekend is not enough. But then again, it never is. Here's the best itinerary for those on a quick weekend getaway. Have more time? We've included some suggestions for extending your weekend into a full-blown vacation.

Book a flight soon to capitalize on the incredible off-season deals in this city that is certainly never off.



Chances are you will be staying near San Juan's main hotel strip, Condado. Drop off your bags in the room, spend the afternoon out on the beach, and situate yourself at the poolside bar by happy hour.

When the sun sets, grab a quick shower and head down the strip to Ropa Vieja for San Juan's best mofongo. Mofongo is the staple dish of Puerto Rican cuisine and consists of a bowl-shaped mound of fried, mashed plantains topped with your choice of meat and drenched in a delicious red sauce. Ropa Vieja boasts the best fare in town.


After dinner, you can either stick around Condado to dance at the area's swanky hotel clubs and casinos or head over to Rio Piedras. Condado is where Puerto Rico's rich and famous come to see and be seen. Home to the University of Puerto Rico's main campus, you'll find a younger, more local vibe along Rio Piedras' happening streets.

Wherever you end up, make sure to take a moon-lit walk down the beach before you go to sleep.



Today is the day to immerse yourself in the European ambiance of Viejo San Juan. To start, head straight to the end of town and explore Castillo de San Cristobal, the Spanish fort that sits atop a high promontory overlooking the entrance to San Juan Bay. The six-level fortification began in 1539 and grew into one of the largest forts built by the Spaniards in the Caribbean. The picturesque Cementario Santa Maria Magdalena de Pazzis, established in 1863, sits just outside the fort walls. Stop by on the walk back to town.

Next, stroll down Fortaleza Street and grab some lunch in one of the old city's alluring, open-air eateries. Top lunch off with some ice cream in Plaza de Armas, where you can sit and people-watch in the heart of the city.


Escape the afternoon heat in one of San Juan's world-class museums. The Museo de Arte de Puerto Rico and the Museo de Arte Contemporaneo de Puerto Rico are just blocks apart in Santurce and equally impressive in their collections. While the first takes a look at the classics and more established living artists, the contemporary museum highlights the best of Puerto Rico's up-and-coming talent.

Back in Old San Juan, Casa Blanca, Museo de las Americas, El Arsenal, and Museo de San Juan will each paint a picture of the island's colorful history.

If museums are not your thing, take the Cataño ferry across the bay to Casa Bacardi to learn about (and taste) the island's famous rum.


Grab a mojito for happy hour and then sit down for dinner in one of the moody, dim-lit dives that dot the old city's side streets.

If a thumping reggaetón club is your ideal Saturday night destination, head directly to Club Lazer, Puerto Rico's #1 night spot. Otherwise, the Nuyorican Café on Cll San Francisco has a rotating schedule of jazz, poetry, theater, dance, and local bands to ooze you into the Latin vibe.

There are plenty of wine bars, cigar houses, clubs, and cafes to keep you entertained all night long in Old San Juan. Alternatively, you could top the night off in one of the gritty underground clubs off of Ave Juan Ponce De León in Santurce.



If you're not lazing away your Sunday morning on the beach in Condado, attending a service at the Cathedral of San Juan de Bautista may be just the cultural experience you're looking for. Dating back to 1521, this is one of the oldest buildings in Puerto Rico and the second oldest cathedral in the New World.

If you're not worn out and packing your bags to head home, here are some ideas to extend your weekend into a full-blown vacation in San Juan:

- Include a day trip out to the El Yunque Rainforest, an easy hour's drive from the capital.

- Take a kayak tour of the bioluminescent bay in Fajardo.

- View an avant-garde film at Caribbean Cinemas' Fine Arts theater.

- Go on a shopping spree at Plaza Las Americas, the largest shopping mall in the Caribbean.

- Catch a show at the Luis A. Ferrè Performing Arts Center.