Antiguo 26
Set in a former Soda Factory, Antiguo 26 serves homemade sodas, craft cocktails, and creative tapas in a setting reminiscent of The Great Gatsby.
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From Thursday through Sunday it's as if there's a celebration going on nearly everywhere in San Juan. Be sure you dress to party, particularly on Friday and Saturday nights; Puerto Ricans have flair, and both men and women love getting dressed up to go out. Bars are usually casual, but if you have on jeans, sneakers, and a T-shirt, you may be refused entry at nightclubs and discos.
Well-dressed visitors and locals alike often mingle in the lobby bars of large hotels, many of which feature bands in the evening. Some hotels also have clubs with shows and/or dancing; the cover generally starts at $10. Casino rules have been relaxed, injecting life into what was once a conservative hotel-gaming scene, but you still won't be allowed in wearing a tank top or shorts. There are more games, plus such gambling perks as free drinks and live music.
In Old San Juan, Calle San Sebastián is lined with bars and restaurants. Salsa music blaring from jukeboxes in cut-rate pool halls competes with mellow Latin jazz in top-flight nightspots. The young and the beautiful often socialize in Plaza San José. Mid-January sees the Fiestas de la Calle San Sebastián, one of the Caribbean's best street parties.
Young professionals as well as a slightly older bohemian crowd fill Santurce, San Juan's historical downtown area, until the wee hours. The revitalized Plaza del Mercado (Calle Dos Hermanos at Calle Capital) has structures—many painted in bright colors—dating from the 1930s or earlier. On weekend nights the area's streets are closed to vehicular traffic. You can wander from dive bars to trendy nightspots and sway to music that pours from countless open-air establishments and the marketplace's front plaza.
Set in a former Soda Factory, Antiguo 26 serves homemade sodas, craft cocktails, and creative tapas in a setting reminiscent of The Great Gatsby.
Dark, sexy, and romantic, this hidden speakeasy is a lovely spot for a cocktail. There's a cigar lounge in the back room, and the sliders are delicious. There's no sign, so look for the three red rings on the door.
Dress to impress at this chic hotel dance club, where a long line of young people (21-plus) wait to get in Thursday through Saturday. Each of the two levels has its own DJ and dance floor.
This legendary dive bar won't win any prizes for decor, but it has an irresistibly artsy and welcoming vibe. Add your own message to the graffiti-covered walls—they have a "B.Y.O.S." policy (Bring Your Own Sharpie)—or hang your business card alongside the hundreds that cover the light fixtures. The jukebox has the best selection of oldies in town, and locals crowd the back room for billiards.
Tucked away in an alleyway off Calle Fortaleza, Old San Juan's newest bar pays tribute to a world selection of natural wines. The lovely owners, an expat husband-and-wife team from New York, passionately serve their carefully curated wines that are farmed organically or biodynamically. It's a great place to start your night or end with a nightcap in a romantic setting. Pop-ups by local chefs are hosted monthly.
For a non-touristy experience, head to this lively dive bar in the heart of Santurce, and order a Medalla or a rum drink with fresh juice. There's often live music being played on the street to a packed house. Be sure to take in the incredible street art on a stroll through the area.
Run by the same guys as La Factoría in Old San Juan, this tropical tiki bar is steps from La Placita. Although it has a charming patio, its dark, cozy interior is a pleasant respite from the busy marketplace, and the bar food is excellent, with a rotating, seasonal menu.
On the roof of Aire de O:live, this sexy, bohemian spot offers some of Isla Verde's best ocean views. The Japanese-inspired menu offers creative sushi rolls, charcoal-grilled skewers, sakanas (Japanese snacks served with sake), and a selection of excellent cocktails.
After a night of drinking at La Placita, head to hipster favorite, La Penúltima, for a nightcap (perhaps a carbonated Negroni) and fantastic late-night bites!
If you love beer, don't leave Puerto Rico without visiting Lúpulo. At the island's largest craft beer bar you'll find over 25 varieties on tap and more than 100 bottles of the finest European and American brews. This casual hipster bar is open late and a great option for night bites.
Scryer Rum is a small-batch, premium spirit that's distilled in Barbados and aged on-site in Old San Juan. The first floor is home to the finishing casks and a beautiful bar that evokes the Roaring '20s. The second floor has a small lounge, and the spacious rooftop overlooks the street. Tours are available by reservation.
Latin America's answer to the Hard Rock Cafe, Señor Frog's attracts both hard-partying tourists and the cruise-ship crowd—no surprise, as it's located directly in front of the dock. (Look for the giant inflatable frog.) The just-okay menu is a nod to Mexico, with south-of-the-border favorites like nachos and quesadillas. When it comes to drinks, expect quantity over quality; their signature is the Yard, a tall plastic cup filled with your favorite adult beverage. There's often live music, a ladies' night, or other special events.