San Diego

Though the iconic highway technically starts 65 miles north, San Diego, with its wide beaches and buzzing brewery scene, is a good place to start your rally up the coast. If you’re looking to stay in the heart of the downtown action, check into the U.S. Grant, a Luxury Collection Hotel, which ditches overtly beachy decor for city stateliness. From there, you’ll have easy access to the sparkling waterfront, the city’s shopping- and nightlife-filled Gaslamp Quarter, and Little Italy—which is home to must-hit restaurants like Richard Blais’s Juniper & Ivy and the cocktail-focused Ironside Fish & Oyster. It will also put you smack-dab in the middle of the city’s craft-brewery circuit—and spending an evening hopping from one micro operation to the next is a must.

If you want to be as close to the coast as possible, try the iconic Hotel Del Coronado—the historic red-roofed resort was a favorite of Marilyn Monroe in its heyday—or head slightly north to La Valencia Hotel & Spa in La Jolla. Both offer access to some of the region’s best beaches and will give you a taste of old-school Southern California glamour. No matter where you stay, on your way out of the city, be sure to budget some time for Balboa Park—a 1,200-acre space that serves as the city’s arts and culture hub. If you’re traveling with the family, stop by the world-class zoo, or just take a stroll through the park’s sweeping neo-Spanish grounds.