Destination: Santa Cruz, California

Where? Northern California, 60 miles south of San Francisco.

What? Numerous right-hand point breaks, reef breaks, and beach breaks.

When? September—May

Why? A cool, laid-back surf city with an endless variety of breaks, sizes, and crowd factors in addition to legendary spots like Pleasure Point and Steamer Lane.

How? Fly into San Jose, California. Then rent a car and take Highway 17 over the hill to start exploring.

Best Place To Stay: The Coast Santa Cruz Hotel is right around the point and within walking distance of Steamer Lane on the West Side. If you get an ocean view, you'll be staring at the beauty of Monterey Bay, the wharf, the boardwalk, the harbor mouth, and a fun little break in front called Cowell's. Rates run $149—169 September through May. For info, call 1-800-426-0670.

Best Place To Eat: There's an amazingly diverse array of restaurants throughout the area. The Palomar (downtown Santa Cruz) and Café Cruz (on the East Side) are just a few of the more popular establishments. For really weird surroundings, visit the Saturn Café (downtown)–it's open 24 hours and is known for its desserts.

Best Place To Liquor Up: The Palomar and The Catalyst (downtown) offer a startling lineup of frothy adult beverages, and if you're lucky, the entertainment will be local pro surfer/DJ Omar Etcheverry of the famous Etch brothers on the wheels of steel.

Crowd Factor: If you want to surf popular spots like The Lane, Pleasure Point, or 41st Avenue, get ready to do battle–they really pack em in. You can stay within the Santa Cruz area and still find a fun, slightly less-crowded break. If you're a true explorer, venture up Highway One in either direction and find your own goods. Oh yeah, the locals can be gnarly everywhere–caution is advised.

Female Factor: It may be cold, but there're tons of hot chicks. From students to tourists and locals, beautiful women are a common sight, both in town and in the water. For viewing pleasure, just walk along the coastal path that runs up the West Side.

Stuff To Bring: In winter, the air temps can get as low as the 30s at night and the water in the high 40s. Bring warm clothes and a warm (4/3) wetsuit with booties. As for the quiver, think thicker. There's a lot of water moving around–a good range of boards, from a high-performance shortboard to a gun, is recommended.

If The Surf's Flat: It's rarely flat–something, somewhere will be breaking. You're only an hour and a half from San Francisco, where you can get into anything you want to–literally. You're also right across the bay from scenic Monterey and only hours away from Lake Tahoe's resorts. Santa Cruz is also home to the legendary Derby skatepark.–Checkwood