Once home to the rollicking saloons of the Gold Rush’s infamous Barbary Coast, Jackson Square today exudes a cool sophistication. The historic neighborhood charms with tree-lined streets and enchanting 19th-century buildings, its former boozy dens replaced by Michelin-starred restaurants and stylish boutiques.
Strolling the neighborhood’s many upscale shops serves as a de facto walking tour of its captivating, historical architecture. Check out the stunning, recently restored Belli Building (circa 1850) where you’ll find modern flannels and tin cloth jackets from heritage outfitter Filson. In a connecting showroom, Shinola gleams with superior, expert-crafted goods such as bicycles, watches and audio equipment. Neighbor Allbirds features sporty, sustainably made kicks fashioned from merino wool in a concept store situated on Hotaling Place, a charming alleyway lined with hitching posts from bygone stables.
On nearby Jackson Street, pop into French clothier A.P.C. for simple yet impeccably designed men’s and women’s apparel, and Guideboat Co. for refined outdoor wear fit for a lakeside weekend in the Adirondacks. At Eden & Eden, browse modern jewelry and covetable home goods, and don’t leave without a local guidebook from the stacks of design tomes at William Stout Architectural Books.
Mingle with the neighborhood’s creative types over pastries and pour overs at Réveille, a jet-black coffee truck parked at Pacific and Sansome streets. Sip contemporary grogs at Barbarossa Lounge, a dramatically lit, multi-level cocktail den with design references to its former life as a jail. At Taverna Aventine, duck downstairs to the speakeasy-style lounge whose eastern wall is a 150 year-old rough-hewn seawall, a reminder of the city’s original shoreline.
In contrast to its rough and tumble past, Jackson Square might now be the only San Francisco neighborhood with multiple three-Michelin star restaurants. Coi recently nabbed a third star with the artful precision of its 10-course, seafood-focused tasting menu. Three-star Quince has long wowed diners with ultra-refined dishes sourced from its organic farm, while its casual next-door sibling, Cotogna, features supple homemade pastas and rustic dishes roasted over a crackling hearth.
At Japanese steakhouse Roka Akor, you can pair buttery Wagyu beef with pristine sushi in a serene dining room or enjoy happy hour bites in a sleek subterranean lounge. Turn down Gold Street, one of the neighborhood’s many atmospheric brick-lined alleyways, and you’ll discover Bix, a dazzling 1930s-styled supper club that serves up classic cocktails and live jazz every evening.