Santa Cruz

This ultra-mellow beach town has a decided split personality—and both sides are cool. First, there’s the woo-hoo family fun of the Santa Cruz Beach Boardwalk, a yesteryear-style esplanade lined with classic coasters, arcade games, corn dogs, and a historic carousel. Then there’s downtown Santa Cruz, where local college students browse for vintage and boho chic, and relaxed restaurants focus on organic, local ingredients.

But at its heart, Santa Cruz is a surf town. This is where the sport was originally introduced in California, and top surfers know that the place to be is Steamer Lane. Need more proof? Nearby lives Jack O’Neill legendary surfer and force behind the O’Neill empire, pioneer of the wetsuit and elder statesman of everything surf in the Golden State. 

In the center of town, away from the beachfront crowds, Pacific Avenue offers many shops with a local twist, including the venerable O’Neill’s where surfer guys and girls can find a bikini or board shorts, flip-flops, or a wetsuit—the creation and design of the city’s favorite son, the legendary Jack O’Neill (he still lives a beach ball toss from the beach here). The independent Bookshop Santa Cruz is packed with happy locals, especially during frequent author talks, and many other boutiques offer art, clothing, and home furnishings (check out the gorgeous artisanal glass at Annieglass).

Next, travel to your last stop—the beautiful “City by the Bay,” San Francisco.