Rugged, retro, and just under the radar, San Diego’s quiet side never looked so good
A Picturesque Weekend in Point Loma
Photo by J.P. Greenwood
Get out on the water with J World San Diego, a sailing school that can teach you the basics in a beginner lesson.

The sea of beach blankets laid out like Scrabble squares from Carlsbad to Coronado—that’s the San Diego we know, even love. Legos and tacos and celebrity  dolphins pirouetting before rows of sun-visored tourists. All fine and dandy, if you’re in the mood for a splash. But for a quieter, more low-key coastal experience, tiptoe to tiny Point Loma, where white sand gives way to rocky shores, and crowds of flesh concede to clusters of picnicking locals. And where a wave of new energy—new restaurants and a place to rest your head—casts a glow on this charming peninsula community. Here are six reasons to get straight to the Point.

1. Take in the city: There’s only one way to really see San Diego: by boat. Get your sea legs with a beginner’s lesson at J World San Diego, a sailing school in Point Loma’s yachting hub. Learn basics, from the parts of the boat to tacking and jibing, in an eight-hour class (from $250). But if you’d prefer to let someone else play captain while you sip Champagne, book a sunset sail ($400 for up to 6) and drink in the views of downtown. 619/224-4774.

Photo by J.P. Greenwood
New on the block: Sessions Public brings primo pub food to the people.

2. The meal you’ve been waiting for: Point Loma has been holding out for a farm-to-table restaurant for quite a while now. And Sessions Public doesn’t disappoint. The menu teems with standout dishes: duck confit Thai summer rolls, spicy Mexican prawn salad, a warm brownie made with a beer-and-bourbon caramel sauce—not to mention a deep list of brews that includes local stars like Ballast Point. Call it pub grub, comfort food, whatever you like. We call it awesome. $$; 4204 Voltaire St.; 619/756-7715.

Photo by J.P. Greenwood
Find fishing gear at Sharkey’s.

3. Hook a halibut: Get to Sharkey’s at Shelter Island Pier on the early side to rent a pole and fish for halibut, bonito, and spotted bass, which dart around the pier. Or rent one of seven kayaks to explore the nooks and crannies of the protected cove. Pole and bait $10, kayak from $20/2 hours; 1776 Shelter Island Dr.; 619/758-1714.

4. Concerts on the water: The annual Humphreys Concerts by the Bay take place in a palm tree–lined venue overlooking San Diego Bay. This month, look for performances by Diana Ross, Chris Botti, and Boz Scaggs with Michael McDonald, whose yacht rock classic “Yah Mo B There” will never sound more at home. From $37;  

Photo by J.P. Greenwood
Stay at  retro-chic Pearl.

5. A jewel of a Hotel: The 23 rooms at the recently remodeled Pearl, a midcentury-modern getaway one block from the bay, are stylishly appointed and reasonably priced (from $129). Sip the signature Pearl Pimm’s Cup beside the vintage, oyster-shaped swimming pool. It’s the same place you’ll meet for Sunday brunch, with bottomless mimosas and favorites like grits and bananas Foster French toast ($$$).

Photo by J.P. Greenwood
Cool down with a Bali Hai mai tai.

6. Your screen-saver views: The San Diego skyline unfolds like one of those panoramic postcards when you’re standing beneath the 1855 Old Point Loma Lighthouse in Cabrillo National Monument ($5/vehicle; 1800 Cabrillo Memorial Dr.; Of course, what sunset isn’t sweetened with a dram or two of rum? Come dusk, grab a window seat at Bali Haí Restaurant ($$; 2230 Shelter Island Dr.; 619/222-1181), a Point Loma institution mixing famously high-octane mai tais since 1955.

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