There's no shortage of places to shop in Silicon Valley but there are five places that have a distinct flavor all their own.
Stanford Shopping Center - Palo Alto (Best Experience)
This beautiful open air shopping center has all the staples you'd expect from a high-end mall, presented in a uniquely Northern California way. Actually, "mall" and "shopping center" don't adequately describe the town plaza atmosphere created by the combination of architectural design and greenery. The Stanford Shopping Center boasts about 200 stores with the best names in fashion, jewelry and even electronics represented. Sweet tooths are rewarded by the impressive La Baguette bakery and the adjacent courtyard where you can enjoy your fresh pastries. Plus you'll find specialty grocery stores and a butcher onsite.
The Great Mall of the Bay Area - Milpitas (Largest Shopping Center)
The Great Mall of the Bay Area in Milpitas is the spiritual opposite of the Stanford Shopping Center. Inside this gargantuan building, you'll find a schizophrenic combination of outlet mall, mid-range retail and family entertainment. And while you won't always find the lowest prices here (since many of the stores like Old Navy are not actually outlets) there are an almost infinite number of places to hunt for bargains. Be sure to wear comfortable shoes and bring a stroller for the youngsters because it's actually possible to walk several miles if you explore the whole mall!
Westfield Valley Fair - San Jose (Best Traditional Mall)
Valley Fair is an extremely popular upscale mall, run in the typically efficient Westfield style with strong anchor stores and brand names. The mall is large, with about 1.5 million square feet of stores, and though walking through all of it is real exercise, it isn't daunting because of the layout. Parents often appreciate the large play areas for children and the enormous food court has outdoor seating which makes for a nice break from the bustle inside. There's bustle outside too as parking is tough on the weekends --- though it (seriously) may be easier than the line for the ladies room during peak times.
Santana Row - San Jose (Most Trendy)
Santana Row, located across from Valley Fair, is actually a relatively new urban residential neighborhood that was master planned to blend a downtown shopping experience with city living. Almost self-conscious about its own elegance, Santana Row is trendy without feeling contrived. Fine dining, wine bars, and even a courtyard chess set complete with two-foot tall pieces round out the experience --- until the weekend comes. Seemingly with the flip of a switch, the Santana Row nightlife becomes "the scene" with music, drinking and entertainment. And with the switch, parking becomes a dogfight in the tight garages.
Gilroy Premium Outlets (Best Bargains)
About an hour south of San Jose, the Gilroy Premium Outlets are a collection of about 150 outlet stores with an enormous selection of major brands and stores for everyone in the family. Because of the popularity of the outlets, the entire town of Gilroy is booming with traditional retailers as well like Costco, Home Depot, Best Buy, and others, making it a good one-stop shopping destination. Traffic between Silicon Valley and Gilroy is sometimes limited by a stretch of Highway 101 which narrows down to two lanes in either direction, and often leads to bumper-to-bumper conditions on weekends.