With sun and surf to spare, California’s second city promises biking, hiking, cross-border cuisine and good vibes galore
Your weekender guide to the best things to see and do in San Diego. Find more travel inspiration for your next Vrbo vacation here.
Often described as L.A.’s friendlier little sibling, palm-dotted San Diego embodies the quintessential Southern California atmosphere. With its near-perfect year-round weather, salty ocean breezes, and all-around good vibes, it’s no wonder that it’s referred to as “America’s Finest City.”
As California’s second-largest city, not only does it boast some of the most beautiful beaches in the country, it’s also home to dozens of charming neighborhoods, each with its own distinctive personality—and plenty of beautiful Vrbos to choose from.
Many visitors start off in San Diego’s bustling downtown and waterfront areas. Here, you get a taste of history and top-notch dining, including Cali-Baja cuisine, fusing flavors from both sides of the California-Mexico border (Tijuana is just a 45-minute trolley ride away).
A pro surfer’s guide to finding the perfect Vrbo
Nearby La Jolla offers plenty of hiking trails and opportunities for retail therapy, while the hip Hillcrest neighborhood, historic Old Town, and beach-rimmed Coronado Island are must-visits. Whether you’re feeling adventurous or want a more laid-back trip, San Diego has plenty to fill a long weekend. Scroll down for your perfect three-day itinerary.
9am: Brunch alfresco
Kick off the day with a hearty breakfast at Little Lion Café in Point Loma, where you’ll find irresistible Benedicts and bowls. Depending on whether you’re in the mood for sweet or savory, pair your dish with a Not-So-Little Lion Mimosa or the sake-infused Le Mer Rouge.
11am: Head for the shore
Venture over to the 1855 Point Loma Lighthouse, as well as the tidepools near Cabrillo National Monument, where you can spot crabs, sea anemones, octopuses, and other creatures.
2pm: Join the Navy
Make your way to downtown’s Embarcadero, where Waterfront Park stretches across 12 acres. San Diego has long been a Navy town, and you’re right in the center of that history here, so stroll along the waterfront to the USS Midway Museum and the Maritime Museum, which includes several historic sailing vessels like the Star of India. Not too far away is Seaport Village, where you can indulge in farm-to-table fare at the new Malibu Farm.
8pm: Go global in the Gaslamp
Have dinner at Zama, an Amazonian-inspired restaurant that blends Japanese and Latin American flavors; you’ll find it in the Gaslamp Quarter, the city’s lively nightlife district, packed with places for a drink afterward. For live music, standout venues include The Rady Shell at Jacobs Park, home of the San Diego Symphony and host to a variety of acts, while Humphreys Concerts by the Bay, at Shelter Island, has beautiful bay views.
8am: Rise and shine with a hike
With locations all over the San Diego area (including La Jolla, Encinitas, and Coronado), local favorite Better Buzz creates hand-crafted coffees, teas, and smoothies that will prepare you for a hike in the cliffside town of La Jolla.
10am: Kayak the sea caves
Head towards the Torrey Pines State Reserve, which has jaw-dropping views of the coast. A hike along Mar Scenic Trail in Del Mar and a kayak tour of the La Jolla Sea Caves are both good (and relatively low-key) options.
1pm: Shop locally
After your hike, visit the Village of La Jolla for lunch at Queenstown Public House, which serves casual New Zealand-inspired cuisine. Follow with an afternoon browsing the town’s many boutiques. Don’t miss Warwick’s, the country’s oldest continuously family-owned and operated bookstore. Check out the store’s event calendar, as there’s something happening almost daily.
7pm: Cap it off with film classics
Head over to Hillcrest, a vibrant LGBTQ+ neighborhood. Visit one of the city’s buzziest new restaurants, InsideOUT, located in the Eitol Towers, for seasonal craft cocktails and California-Mediterranean fare. Then head over to Cinema Under the Stars in nearby Mission Hills, an outdoor theater that screens both current and classic films.
9am: Amble around the Old Town
Hop around the shops at the historic Old Town Market for gifts like turquoise jewelry and Mexican textiles, then pick up tasty pastries and creamy cappuccinos at Garden Coffee, tucked away in a lush garden.
11am: Lions and tigers and bears...
Next head to historic Balboa Park, the country’s largest urban cultural park, where you’ll find 18 museums, palm-lined ponds and gardens, and San Diego Zoo’s 3,700 animals. Linger awhile to admire the park’s Mediterranean architecture.
2pm: Feast on Mexican fusion cuisine
Walk or drive the short distance to Banker’s Hill for Barrio Star, a lively joint that describes its cuisine as Mexican soul food—a blend of Latin and Asian flavors. Its beer and cocktail menu includes a roasted jalapeño blackberry margarita for added spice.
4pm: Bike around Coronado Island
Afterward, visit Coronado Island for its small-town charm; get there via trolley, boat, or car. Rent bikes and pedal along the 16-mile bike path that encircles the island. Be sure to visit the ornate Hotel del Coronado—affectionately referred to as “The Del.” Established in 1888, it’s said to have inspired Wizard of Oz author L. Frank Baum, who lived there for months at a time. Enjoy Mediterranean coastal cuisine at Serẽa, located inside the hotel.
Danielle Bauter is a freelance writer and editor based in Southern California. Her work has appeared in Condé Nast Traveler, Lonely Planet, Westways Magazine, and Fodor’s Travel, among other publications.
