San Diego Challenge Tour

Depart San Diego Airport and make a beeline for Balboa Park, the cultural heart of San Diego. Start by visiting the San Diego Zoo’s apex predators—polar bears, crocodiles, and big cats—then mingle with gentle giraffes and astounding elephants. At some point during the day, consider a brunch, happy hour, or dinner excursion on a City Experiences cruise out on San Diego Bay. Don’t miss the San Diego Air and Space Museum to see artifacts from aviation superstars like Charles Lindbergh and Amelia Earhart. For lunch, head for Liberty Station’s Stone Brewing World Bistro and Gardens, housed in a former U.S. Navy mess hall, to sip craft beer and play grass-court bocce. Then check in to the Manchester Grand Hyatt in Seaport Village (the 40th-floor rooms have blue-water views). Take a 15-minute walk to Petco Park and arrive in time for first pitch at a San Diego Padres game. End your night at Aero Club Bar, an aviation-themed watering hole serving 1,000-plus whiskeys and an awesome pinball lineup. 

Head upcoast 25 miles to Encinitas, where pickleball lovers hang out at Bobby Riggs Racket and Paddle Club. Sign up for a lesson or drop in for open play, and check out exhibits devoted to Riggs, the tennis star who lost to Billie Jean King in 1973’s infamous “Battle of the Sexes.” This sand-and-sea city is also a top beach spot, whether you want to site back and watch top-notch surfing at Swami’s Beach or try it yourself. Sun and sand make you hungry, so beeline to Modern Times Far West Lounge for plant-based fare and 30-plus rotating taps. Legend has it that fish tacos were invented in Encinitas, so sample the local flavors—try salmon tacos at Fish 101, mahi mahi tacos at The Taco Stand, and red snapper tacos at The Fish Shop. 

If you’re in Carlsbad with kids, LEGOLAND California is a must. Marvel at plastic-brick-built dinosaurs, remarkably detailed mini-cities, and kid-scale pirate ships, and check out new attractions like LEGO Ferrari Build & Race. Kids can build their own Ferrari out of LEGO brinks, then race their car around a real track. If you’re traveling without youngsters, take on an adult challenge with So Cal Surf Lessons at Carlsbad Beach. Master your popup, then paddle out and catch a few waves. Afterward, head over to the Museum of Making Music to jam on electric guitars and learn how various instruments, from Steinway pianos to the ukulele, were invented. In late afternoon, swing your golf clubs at Carlsbad’s Park Hyatt Aviara, then sleep in luxury at this lush, 250-acre oasis. 

Midway between San Diego and Palm Springs, Temecula has established itself as Southern California’s go-to wine country thanks to rich soil and nearly 50 wineries dotting the sun-kissed valley. Start by exploring Old Town Temecula’s 12 blocks of antique shops, galleries, brewpubs, and restaurants. At Temecula Olive Oil Company, taste extra virgin olive oils and small-batch vinegars. Make plans to redecorate your living room with salvaged and artisan home goods from Reclaimed at Main St. Market. Play old-school arcade games at Coin-Op Game Room. When evening falls, don your cattleman hat and strut your two-step on Temecula Stampede’s 4,000-square-foot dance floor, then go for broke with a wild ride on the mechanical bull.

Warner Springs is one of San Diego County’s last rural ranching outposts. This undulating landscape of big sky and grass has more cows than people, but visitors will find a surprising amount of fun. Taste wine at a handful of family-run vineyards: Shadow Mountain, Hawk Watch, and Emerald Creek. Go for a two-hour horseback ride from the Warner Springs Ranch stables. Park by the Cal Fire Station and hike the Eagle Rock Trail to a cluster of boulders shaped like an eagle with wings spread wide. See what it’s like to soar like an eagle at Warner Springs Gliderport. Sky Sailing’s basic half-hour sailplane tour is smooth and gentle, but if you request an “aerobatic” ride, your pilot will flip your world upside-down. 

Surrounded by Anza-Borrego Desert, the village of Borrego Springs is a place where locals understand the merits of slow-paced pleasures. Many spend their days hiking, making art, lounging poolside, and reading books in their sunny backyards. For visitors, the town’s fantastical outdoor art is a big attraction: Ricardo Breceda’s menagerie of metal sculptures lies hidden in plain sight across three square miles of desert. Try to find all 130 works, including an elephant, saber-toothed cat, serpent, and Tyrannosaurus rex. After searching for art, head into town for no-fuss dining—pancakes at the Red Ocotillo, burgers and BLTs at Carlee’s, enchiladas and margaritas at Pablito’s. Book a casita at the luxurious La Casa del Zorro or patio room at the pink-adobe Borrego Valley Inn, and plan to stay up late for desert stargazing. 

Motor into Julian, San Diego’s favorite mountain town, for some competitive apple-pie eating. Purchase a buttery, gooey slice at each of this mountain town’s three bakeries—Mom’s Pie House, Apple Alley, Julian Pie Company. Take a few bites of each, consider their merits, and crown the winner. Then work off crusty calories with a hike up Cuyamaca Peak, San Diego County’s second-highest summit (6,515 feet) and one of the top treks in Cuyamaca Rancho State Park. For a mellower pursuit, get a history lesson at the Pioneer Museum and tour the Eagle and High Peak Mines, where you’ll learn about Julian’s 1870s gold rush. Sleep at the Julian Gold Rush Hotel, an 1890s Victorian landmark. 

Make a final stop in El Cajon, one of San Diego’s most culturally diverse suburbs. Main Street is a hot spot for Mediterranean and Middle Eastern food: you’ll want to try falafel and kabobs at Mal Al Sham, baked pompano fish and tanoor bread at Ali Baba, and lamb shank stew at Al Azayem. Before you start eating, pull in to Sky Combat Ace for a high-stakes aerial competition—you’ll fly a real stunt plane in a simulated dogfight. Battle against your friends or an instructor, and see the loser’s plane finish in a trail of “smoke.” El Cajon offers mellower pursuits too. Visit the Olaf Wieghorst Museum, a trove of Western paintings and sculptures by the 20th-century Danish immigrant. The museum’s grounds, filled with mature cacti and succulents, occupy an entire city block. When it’s time to head back home, San Diego’s airport is just 20 miles due west.