La Placita in Santurce (Thurs., Fri. and Sat.) for music/food
La Respuesta in Santurce on Monday nights
Newyourican Cafe in Old San Juan for live salsa music
Kiosko de Bouriqua in Loiza (rte. 187) for alcapurrias (fritters)

There's a dope interactive P.R. music history museum in Ponce (90 minutes south of San Juan). If you go stop at King's Ice Cream in downtown Ponce.

Beaches:
Luquillo
Playa Sucia
Flamenco Beach (Culebra)
Red Beach (Vieques)

I highly recommend getting a flight from a smaller airport (Isla Verde or Cieba) to Vieques or Culebra. Its inexpensive, a 20 minute ride, and you can avoid the hellish ferry.

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"the true path to creativity is to burn out" - Jean Michel Basquiat