A Perfect Weekend in San Diego

Take in the best of America’s Finest City

Few destinations around the world boast the diverse geography, culture, gastronomy, and climate that you’ll find in San Diego. With so much beckoning for exploration, it pays to break up a visit by neighborhood, offering ample time to soak up all that comes together to give this sunny seaside destination its well-deserved moniker.

Downtown sparkles on descent into San Diego, and just minutes from the airport, it’s an exciting and easy first stop after touching down. If you arrive on a Saturday, stroll through the weekly Farmers Market in Little Italy, where in addition to the standard fresh produce, you’ll find gifts and unique items created by local artisans. 

San Diego is renowned for its craft beers, and you’ll find plenty to sample at Burgeon at the Arbor in Little Italy. While IPAs tend to get all the attention, it’s the Pistil German Pilsner that’s a must-try on the list for its crisp flavor and effervescence. It’s a perfect companion to shrimp tacos and a great way to fortify after a flight or before walking around town. 

San Diego’s pro baseball team, the Padres, play downtown in what is widely acknowledged as the most beautiful baseball stadium in the country, Petco Park. If the team is in town, catch a game and make sure to go hungry. The stadium features incredible dining options from some of the most popular destinations in the region, including Seaside Market’s “Cardiff Crack” tri-tip, Hodad’s burgers, Pizza Port pizza, and Deckman’s at the Draft, a north-of-the-border outpost by renowned Chef Drew Deckman, whose eponymous restaurant in the Mexican wine region of Valle de Guadalupe holds a green Michelin Star. The ballpark recently debuted a new ‘70s-inspired speakeasy concept, The Diamond Room, a 50-seat destination perfect for a pregame happy hour – or a post-game celebration. The stadium also made a recent multimillion-dollar investment in Gallagher Square, an outdoor space that, in addition to the main stadium, hosts a multitude of concerts and events throughout the year. 

For more live entertainment, Downtown San Diego and its bay are the picturesque backdrop to another breathtaking outdoor venue, The Rady Shell at Jacobs Park. This acoustical marvel on its own mini-peninsula hosts performances from the San Diego Symphony to household names like James Taylor, Harry Connick Jr., and Paul Simon. Purchase traditional stadium seating or buy lawn seats to have a picnic under the stars as you enjoy the performance while boats in the bay or the harbor jockey for space to pull up nearby and listen along. 

San Diego has also proven it’s a venerable dining destination. In Little Italy, Herb & Wood is a cornerstone of the neighborhood scene. Helmed by Top Chef alum Brian Malarkey, it is consistently delicious and casually, cool. For an edgier vibe, nearby steakhouse Born & Raised rewards those able to secure reservations with Art Deco-inspired interiors and cheeky décor, a novel-length wine and cocktail menu, and old-school touches like tableside Caesar Salad preparation. 

If nothing sweet on the post-dinner menu intrigues you, a stop at Extraordinary Desserts will not disappoint. A mainstay downtown for more than two decades, this spot will tempt even the most disciplined diners into indulgence, with coffee that’s equally worthy of the extraordinary name to accompany any treat. 

When it’s time to turn in, check in to Pendry San Diego. Situated in San Diego’s historic Gaslamp District, it’s ideally situated to explore downtown, walking distance to Petco Park and Seaport Village or a minutes-long car ride to other nearby destinations including the theaters, Little Italy, and the harbor. You won’t want to spend all your time away from the hotel, however; its rooftop pool is a San Diego destination unto itself, and signature restaurant Lionfish is led by lauded San Diego-bred Chef JoJo Ruiz, whose sustainable practices have earned James Beard accolades. 

Drive just under 15 miles north along the coast and you’ll land in La Jolla, a coastal gem whose nickname is “the Jewel.” One look at the ocean from La Jolla’s bluffs or sandy shore and it’s easy to agree — it’s nothing short of dazzling. A popular playground for Hollywood royalty as well as home to athletes, celebrities, and notable personalities past (Gregory Peck, Raquel Welch, Theodore Geisel aka Dr. Seuss) and present, La Jolla radiates a timeless elegance that is captivating.  

Start your day with breakfast at Pepino Eatery & Bakeshop, a Peruvian-inspired restaurant by Sebastian Becerra, whose resumé includes the three-Michelin-Star Eleven Madison Park in New York. When you’re fully charged, head out to shop around La Jolla’s village, making sure to stop in at Boulevard, a highly curated consignment shop created by owner Kate Whitney, an engaging multi-hyphenate (writer-director-actress-stylist) who takes pride in bringing together pieces at all price points for every customer who enters her store. Warwick’s, the oldest continuously family-owned bookstore in the country, is just a couple blocks away on the same street. It’s a great place to find books, of course, but it also offers unique gifts and maintains an impressive calendar of events, author appearances, and more.  

When it’s warm, rent a kayak and paddle around La Jolla Cove, and afterward, brave the stairs to the Cave Store and take a self-guided tour of an old bootlegger’s tunnel. If you’re looking for a different way to cool down, head to Instagram-famous Greek frozen yogurt shop Myka, located on La Jolla’s main thoroughfare, Prospect Street. You’ll likely be able to locate it by the line that winds out from its doors, but the sweet treat is worth the wait. 

Anchoring Prospect Street and sitting regally on the bluffs overlooking the ocean is the historic La Valencia Hotel, a pink-hued grande dame whose history is interwoven with La Jolla’s for nearly a century. Nicknamed “La V” or “The Pink Lady,” an homage to a mosaic that adorns a wall in its garden, the Mediterranean-style hotel has an effortless glamour that’s as enchanting today as it surely was when its very first guests checked in. 

A short walk south along Prospect from La Valencia Hotel finds you at the Museum of Contemporary Art San Diego, a modern destination showcasing an array of genres both in its own collection and as part of exhibitions. Until November 8, the museum hosts The Dean Collection Presents: Hometown Heroes, featuring works from the personal collection of La Jolla residents Alicia Keys and Swizz Beatz. 

Dining opportunities in La Jolla are bountiful. Snag a reservation at Michelin-Starred Lucien or savor authentic Italian fare at Marisi. For a truly iconic La Jolla experience, book a table at The Marine Room, which sits on the sand and where waves can crash against the dining room’s expansive windows at high tide. 

Of course, there’s so much more to San Diego than its waterfront and beaches, but when they’re as postcard-worthy as this, they’re a great way to anchor a weekend visit to America’s Finest City.