1800 Cabrillo Memorial Dr
San Diego, CA

Easily traversable pathways are all abound in Point Loma, from Cabrillo National Monument to the park-side Liberty Station trail that runs all the way over a pedestrian bridge to the airport, to the newly paved path that leads you on a curvy ride from Shelter Island past the marinas and eateries over to America’s Cup Harbor. Plan to pause several times for pictures—these are some of the most postcard-worthy views of the city skyline. For a more strenuous ride, bike along Catalina Boulevard up to Cabrillo National Monument, where you'll be rewarded with panoramic views of the ocean, Mexico, the Coronado Islands, and San Diego Bay. Bring binoculars to spot whales. For an easy scenic stroll that many locals call an evening ritual, try Bessemer Path, which begins just southwest of the San Diego Yacht Club gate. Or head to the south end of Sunset Cliffs Boulevard for sandy paths, crashing waves, and a sunset view dotted with surfers and seagulls.

1800 Cabrillo Memorial Dr
San Diego, CA

Experience San Diego's history beginning with the Old Point Loma Lighthouse within Cabrillo National Monument, which is open daily and allows visitors to climb all way the up to where the light was first lit in 1855. For a sense of the region’s military history, pay a visit to Fort Rosecrans National Cemetery, where thousands of soldiers are buried overlooking the bay. The NTC Arts District housed within Liberty Station is home to dozens of San Diego’s artistic anchors. From the Women’s Museum of California and Jean Isaacs San Diego Dance Theater to the New Americans Museum, you can't stroll very far through the north end of the sprawling campus without running into a new gallery, pop-up performance, or Instagram-worthy public art moment.

4990 N Harbor Dr
San Diego, CA

The Point Loma area holds some of the best brunch spots in town, made even better by the harbor views. Jimmy’s Famous American Tavern (that’s J-FAT to locals) offers a classic brunch menu with Bennies, seafood options, and bottomless mimosas in a modern setting right on the bay. Bonus for those with kids: The outdoor patio is within view of a big, grassy park next door. For a more elaborate spread, head over to Bali Hai, a San Diego institution that’s been run by the same family for over 50 years. They've got buffet-style brunch with Polynesian influence and stunning views straight across the bay to the skyline. The bar is famous for its mai tai made with five kinds of rum, and don't miss the “Goof on the Roof” of the building—a beloved local landmark.

2805 Emerson St
San Diego, CA

Because the area is home to so much of San Diego’s history as a fishing and port town, its dining scene hews more classic than trendy, attracting those looking for a taste of real San Diego. At the fish market in Point Loma Seafoods you can snag fresh fillets for the grill or a picnic; just muscle your way through the crowds up front to place an order. Or, sit down and enjoy the full restaurant with wine, beer, and a breezy second-floor deck with views to downtown. For something more low-key, try Mitch’s close by. It’s more of a seafood joint than a restaurant, where you'll likely be eating alongside salty sailors, fishermen, and their families. Another longtime family-owned spot on Shelter Island Drive, Brigantine, serves up classics like fish tacos with local beers on tap. For something a little more cozy, try Old Venice, tucked away just off of Rosecrans. White-on-white decor, twinkle lights strung about the back patio, a classic Italian menu, and a buzzy bar scene next door with live music most weekend evenings.

2820 Historic Decatur Rd
San Diego, CA

For a taste of everything San Diego, a visit to Liberty Public Market is a must. Check out the local butchers and fish mongers, farm-fresh produce, and small outposts of some of the city’s best restaurants. Kids will love the gelato and the big, grassy seating area outside. Foodies and beer lovers will love to hunt, peck, taste, and sip their way through the samples. Don't miss the stand-up oyster bar or the Bao Bar, where you can grab a steamed bun stuffed with savory fillings and pair it with a smoothie or boba drink. Stop by Mess Hall for a glass of red or white sangria. Sundays mean live music on the outdoor patio, and most stalls offer happy hour specials during the week from 3 to 6 p.m.

5000 N Harbor Dr
San Diego, CA

Point Loma is home to one of the fun on the water and one of the largest commercial fishing fleets on the West Coast. If a slow, breezy sail through the bay is more your taste, you can charter a ride from one of the companies posted up along Shelter Island Drive, or stop by the Sun Harbor Marina to rent kayaks or stand-up paddleboards for the day. The flat, calm waters from Shelter Island Yacht Basin over to La Playa are ideal for an easy, scenic paddle. It's easy to get hungry on the water - before you head out, don't forget to hit up Stars & Stripes deli for provisions. You can also head over to Fisherman's Landing on Scott Street near Shelter Island to sign up for a full- or half-day excursion on one of the big fishing boats that regularly bring home healthy catches of yellowtail or sea bass.

2241 Shelter Island Dr
San Diego, CA

Humphreys Half Moon Inn is a classic Polynesian-style resort with one of San Diego’s most underrated gems: An outdoor concert venue on the bay with a view of the docks. The venue is intimate—just a few hundred seats—which is part of the draw for acts like Stevie Wonder, Steely Dan, and Diana Krall. Locals paddle up into the harbor just outside the venue for freebie views, but anyone can purchase tickets in advance. And there's not a bad seat in the house.

Point Loma

San Diego, California, United States

You know that a peninsula is worthy of national monument status when even the "new" lighthouse has been safely guiding ships into port for over 125 years. The city's history can be traced back to this very spot, and today the area is dotted with pristine marinas, dockside dining, and miles of walking and hiking paths that beckon locals and tourists alike who are looking for fun on the waterfront.