The Little Italy neighborhood just north of downtown San Diego is not your typical stretch of red-checkered-tablecloth eateries. Not only does the neighborhood boast of being the largest “Little Italy” in the United States—spanning 48 square blocks—but its cultural offerings extend well beyond its Italian heritage.
You can still see signs of the Italian-immigrant community that settled here in the 1920s to work in the then-booming tuna industry: the bocce courts at Amici Park, the Italian Renaissance–style frescoes at Our Lady of the Rosary Catholic Church, and the imported cheeses and old-school deli sandwiches at Mona Lisa Italian Foods. A few hotels in Little Italy play off that heritage, too, like the 190-room Porto Vista Hotel with its mod-meets-Mediterranean aesthetic, and The Carté Hotel, part of the Hilton Curio collection, which has a sea-to-table restaurant and the Fonte di Vino wine bar.
Staying in Little Italy gives you easy access to the rest of downtown, as well as nearby Balboa Park, Point Loma, and Coronado. But it’s tempting to stay put and taste your way around this hotbed of acclaimed restaurants that spans many different cuisines. For starters, there’s sumptuous steakhouse Born & Raised, the Japanese small plates at Cloak & Petal, and the almost-too-pretty-to-eat cake slices at Extraordinary Desserts.
Head to Kettner Boulevard—nicknamed “Top Chef Alley"—to experience a few restaurants created by alums of the Bravo series. Brian Malarkey’s Herb & Wood offers rustic wood-fired dishes and craft cocktails, while Richard Blais operates two restaurants next to each other (the molecular gastronomy–influenced Juniper & Ivy and the fried chicken–centric Crack Shack). Little Italy is also home to two Bib Gourmand restaurants, which Michelin recognizes for their balance of quality and good value: Morning Glory, known for its fluffy soufflé pancakes, and Kettner Exchange, with its rooftop bar and creative takes on classic comfort food (like a pork-belly “Pig Mac”).
Nearby, the Piazza della Famiglia offers another culinary nerve center, as well as plenty of outdoor seating and evening live music. Browse its Little Italy Food Hall for a full cocktail bar, gelato, and a variety of counter-service options such as the lamb tacos at Not Not Tacos, created by San Diego–based TV chef Sam “The Cooking Guy” Zien. Come on Saturdays to explore the Little Italy Mercato, an outdoor European-style farmers market where you can find local olive oil, fresh bread, and gourmet goodies.
Little Italy’s bar scene is a blend of old and new, too: Sip a pint at The Waterfront Bar & Grill (whose liquor license goes back to the 1930s, making it the city’s oldest bar) or sample San Diego’s beer scene at Bottlecraft and the downtown branch of Ballast Point Brewing. Or take a ride while sipping a Sazerac at Wolfie’s Carousel Bar, whose centerpiece is a slowly rotating, 24-seat carousel inspired by a Looff classic.
Between meals, explore Little Italy’s unique stores. Browse the surf fashions and gear at Atacama or the cheeky gifts (like anatomically correct heart necklaces) at Love & Aesthetics. Stroll Kettner again to peruse the art galleries and decor shops of its Arts & Design District. Check out the sleek Danish Modern pieces at Klassik and the dazzling mish mash at Architectural Salvage—a treasure trove of vintage light fixtures, chandelier crystals, and antique doorknobs.