Santana Row and Valley Fair, Santa Clara
Santana Row and Valley Fair, directly across from one another on Stevens Creek, complement each other by filling in each others’ gaps. Valley Fair has been providing the valley with tried-and-true mall stores since the middle of the last century, and Santana Row is the new kid in town, bustling with trendy shops, eateries, and even apartments for shopaholics who think: “I would live here if I could.”

Downtown Menlo Park
On the inside of El Camino, downtown Menlo Park is the ultimate in cute and quaint. Situated mostly on Santa Cruz Avenue, Menlo Park’s downtown looks like it hasn’t been touched in about sixty years, and the shopping selections include quintessential small-town, main-drag offerings—a candy shop, bookstore, florist, stationery store and several corner cafes—as well as some fine-dining options and some of the best home-furnishing stores in the valley.

Downtown Saratoga
Big Basin Way and the surrounding downtown area of Saratoga offers plenty of opportunity to drop some serious cash. Saratoga feels like an escape from the city, and has plenty of spas, wineries, boutiques and art galleries that are worthy of spending “you” time on.

Downtown Los Gatos
Hop on 85 or 17 South and head down to tony Los Gatos for a retail retreat. Downtown Los Gatos has a substantial selection of unique specialty shops and familiar favorites like Powell’s Sweet Shoppe.

University Avenue, Palo Alto
Great shopping options are within blocks of a college campus (which is sort of counterintuitive, considering college students aren’t famous for having a lot of disposable income). University Avenue in Palo Alto, near Stanford, boasts several worthy places to drop some dollars, including well-known retailers like the Apple Store alongside local boutiques, restaurants and coffee shops.

Lincoln Avenue, Willow Glen
Lincoln Avenue is a cute little stretch of shops and restaurants running right through residential Willow Glen. Packed with wine shops, clothing boutiques, salons, and the famous Hicklebee’s, it’s made for a sunny, afternoon stroll.

Campbell Avenue, Campbell
Campbell Avenue is a little slice of oddball retail heaven in the otherwise residential Orchard City. Afternoons can easily be lost wandering in and out of curious shops like Recycled Bookstore, 23 Skidoo Vintage, and Toys Toys Toys.

San Jose Flea Market, San Jose
Though certainly more ethereal than the other districts on this list, the San Jose Flea Market has everything that can’t be found anywhere else. Covering 120 sprawling acres every weekend for the last 50 years, the flea market not only has something for everyone, it has it in two colors.

Downtown Santa Cruz
The best time to hit the shops in downtown Santa Cruz is late October or early November, when the summer crowds have left and long holiday shopping lists await. Pick up some books at Logos, indie-label duds at New Deal, or a couple pounds of artisan coffee at Santa Cruz Coffee Roasters.

The Alameda, San Jose
It’s only a few blocks long, but on the stretch of the Alameda that runs from Taylor Street to Diridon Station, you can find fabulous gifts at several stores. Find a great deal at Black and Brown Vintage, read up at Recycle Bookstore, or snag a cup at Crema Coffee Roasting.