510 Stevenson St., Mid-Market
A friend (who happens to operate a storybook organic winery in Tuscany called Querceto di Castellina) turned us on to this Mid-Market pizza-and-wine spot. And this friend knows her wine and her pizza. Montesacro specializes in Roman-style pies called “pinsa,” oval-shaped, puffy flatbreads topped with tasty cheeses, meats, and veggies. These charred pinsa (try the “Ostia” topped with pecorino, grilled artichokes, fresh mint, and bottarga) are perfect for sharing, with a few antipasti like meatballs or fresh-from-Italy burrata doused in pesto. The food—and the minimalist setting—is so elegant for a weeknight dinner (there’s also an outdoor terrace). Lastly, Montesacro’s little grocery section is the ideal hunting ground for last-minute gifts, pantry items, and even fresh pinsa dough to rustle up your own version at home.
San Francisco Proper Hotel
45 McAllister St., Mid-Market
We stand behind anything Kelly Wearstler lays her bejeweled fingers on. The Wearstler-designed San Francisco Proper Hotel is a reason in itself to come here for a weekend. Located in the gritty-cool Mid-Market area, the Proper’s aesthetic echoes that of the surrounding streets. Interiors are a mashup of old and new, of clashing and complementary. Walking into the color-saturated lobby—with its medley of mirrors, paintings, and eccentric prints—feels instantly welcoming. Both the vibe and the music are intentionally upbeat. Guest rooms are on the small side but incredibly comfortable, and in a city as crowded as San Francisco, the bedside concierge tablet is a godsend for both recs and reservations. After supper out on the town, the best way to wind down is with a cocktail or steaming cup of tea on the wraparound rooftop, warmed by the firepits.