La Playa, San Diego, CA

La Playa is San Diego's bayfront strip on the Point Loma peninsula, and on a breezy weekend the view from its streets is mostly sails. The name comes from the beach where trading ships once anchored and crews stored cattle hides, decades before downtown took shape. Homes here are large custom houses on the slope above the water, with the most prized lots right on the bay. A few of those bayfront properties keep small private piers for their own boats. The San Diego Yacht Club and the Southwestern Yacht Club both sit along this shore, and they set much of the neighborhood's rhythm, down to the clink of rigging after dark. Shelter Island Shoreline Park is where people walk, picnic and watch boat traffic move through the channel. It follows the island's bay edge, with a playground along the way, a public launch ramp and Pacific Rim Park out near the tip. Farther down the peninsula, Cabrillo National Monument has the Bayside Trail and tide pools, and Sunset Cliffs Natural Park is a quick drive west when you want the open ocean instead of the bay. Bali Hai has been pouring mai tais on Shelter Island since 1954, and its Polynesian plates come with a waterfront view and a tiki mascot. For fish tacos or a plate of fried fish, Point Loma Seafoods, a fixture since 1963, sits a few minutes north in Roseville. Errands take the car. Jensen's Foods, up the hill at Catalina and Talbot in the Wooded Area, handles groceries with a meat department and a deli counter, and Rosecrans Street carries you north toward Midway and the freeways for everything else. There is no shopping street inside La Playa itself, so even a carton of milk means a drive. What you get back is a quiet hillside, the bay at the bottom of the street and a yacht club calendar that shapes the week.