Santa Cruz

The ultra-mellow beach town of Santa Cruz along Highway One has a decided split personality, and both sides are cool. First, there’s family fun at the Santa Cruz Beach Boardwalk, a yesteryear-style esplanade lined with arcade games, corn dogs, a wooden roller coaster, and a historic carousel. Then there’s downtown Santa Cruz, where college students browse for vintage and boho chic, and down-to-earth restaurants focus on healthful meals made of organic, local ingredients.

If you love nature, Santa Cruz makes an excellent launching pad. Board a boat tour from the wharf for whale-watching—grays, blues, or humpbacks, depending on the time of year—or take a winding drive in the Santa Cruz Mountains to see the ancient trees at Big Basin Redwoods State Park. And there’s another nature-inspired gem tucked in these hills: a generous selection of wineries, most specializing in Pinot Noir, Chardonnay, and Cabernet Sauvignon.

But at its heart, Santa Cruz is a surf town, dating back to 1885 when three visiting Hawaiian princes rode the local waves on redwood planks, and where today’s top surfers seek out quintessential California breaks at Steamer Lane and Pleasure Point. Need more proof? The late legendary surfer Jack O’Neill, wetsuit pioneer and elder statesman of everything surf-related, made Santa Cruz his home. The O’Neill Coldwater Classic and other international surfing contests take place here every year.

The century-old Santa Cruz Wharf is the longest wooden structure of its kind on the West Coast—a staggering 2,701 feet/823 meters long. Walk to the end to get a bird’s-eye view of Steamer Lane surfers to the north, or come at dusk to watch the lights glow on the colorfully lit Santa Cruz Beach Boardwalk. Along the waterfront, you can rent kayaks, standup paddleboards, or motorboats. Stroll past the fresh fish restaurants and souvenir shops and strike up a conversation with fishermen angling for perch, rockfish, and lingcod. Better yet, join ’em. You don’t need a license to fish from the pier, and local tackle shops can get you outfitted.