Concierge.com's insider take:
San Diego's version of Rodeo Drive, La Jolla is a high-end shopper's paradise. Small fashion boutiques selling ridiculously expensive white pantsuits, fine art galleries lined with oil paintings and modern sculpture, and diamond-filled jewelry shops can be found on a handful of blocks surrounding the always-tony Prospect Street. Hillcrest is a hip, urban (and predominantly gay and lesbian) neighborhood just northeast of downtown San Diego. It's home to an eclectic mix of shops that hawk everything from used clothing to books to hardware to sex toys. The Hillcrest Farmer's Market is held every Sunday from 9 a.m. to 1 p.m. on Lincoln Street. Set alongside the Old Town State Historic Park, Bazaar del Mundo is a vibrant—albeit touristy—collection of shops full of jewelry, fashion, gifts, and arts and crafts, mainly from Mexico and Central and South America (www.bazaardelmundo.com). Most of the shopping in Ocean Beach is based around Newport Avenue, with its quirky collection of shops including beachwear shops, antique stores, surf shops, and even a pair of true head shops. Every Wednesday there's a regular Street Fair/Farmer's Market on Newport.