Gilroy Premium Outlets in Gilroy, Calif., caters to savvy shoppers.
SHOP In a refurbished lumber mill along the Deschutes River, the Old Mill District houses 49 retailers, including REI, Coldwater Creek, and Orvis. (541) 312-0131, theoldmill.com.
EAT Behind the rows of gleaming kitchen gadgets at Allyson's, you'll find a gourmet deli offering creamy roasted tomato soup and an arugula and prosciutto sandwich, all for $7. (541) 749-9974, allysonskitchen.com.
STAY Book a room at McMenamins Old St. Francis School and enjoy a fireside bar, movie theater, and 100-degree soaking pool. From $114. (877) 661-4228, mcmenamins.com.
SHOP Throngs of pedestrians crowd Santee Alley's three narrow downtown blocks in search of designer knockoffs (sunglasses, bags, clothing, jewelry) before the originals even hit the shelves.
EAT Lunch on a bacon-wrapped Alley Dog, and when your day is done, walk six blocks to Colori Kitchen for an Italian dinner of handmade tagliolini ($16). (213) 622-5950, colorikitchen.wordpress.com.
STAY Relieve street-bargaining stress with a deep sleep on organic cotton linens at O Hotel, a short walk from the Fashion District's highlights. From $126.* (213) 623-9904, ohotelgroup.com.
SHOP Browse Gilroy Premium Outlets' 150 stores for high fashion (Polo Ralph Lauren, Guess, DKNY Jeans) and fine cookware (Le Creuset, Calphalon). (408) 842-3729, premiumoutlets.com.
EAT About two miles south at Carnitas Michoacan, mountains of mouthwatering pork are paired with an array of salsas caseras. The house taco plate with rice and beans goes for $9.50 at lunch. (408) 847-8812.
STAY Shopped till you dropped? Drive 10 minutes south to San Juan Bautista. A whirlpool bath awaits at Posada de San Juan. From $88.* (831) 623-4030.
This article was first published in November 2008. Some facts may have aged gracelessly. Please call ahead to verify information.