Welcome to It’s a Date, a series of idea guides to help you navigate your love life in the Bay through thoughtfully planned and curated itineraries, field tested by our staff. Today, play like a local in one of San Francisco’s most storied neighborhoods: North Beach.
North Beach—San Francisco’s Little Italy—is known for being touristy, but that doesn’t mean it can’t be a thrill for locals, too. And what makes it so celebrated among visitors lends itself well to a night of romance: a colorful history, boisterous street activity and picturesque vistas grounded by the unmistakable profile of the Transamerica Pyramid.
We went beyond the star-studded Columbus Avenue, the main thoroughfare of North Beach that’s home to destinations like the Tosca Cafe and City Lights Bookstore, to craft an itinerary a la a native San Franciscan. Start with strolling and window shopping, continue with cozy dining and end with dinner and drinks—now that’s amore.
Great For: Second or third dates, music lovers
Vibe: Italian, old school San Francisco
Time: 4-5 hours
Slow Stroll on Grant
Dusk is divine in North Beach. Start your date in the early evening strolling, and there’s no better place to do it than Grant Avenue. Begin at Grant and Union and walk by the recently reopened Savoy Tivoli, with its open-air and enormous streetside windows practically begging you to stop and have an aperitif to loosen your inhibitions. But really you should keep walking, so you can browse places like Professor Seagull’s Smartshop and Gallery, which specializes in psychotropics, and the Fishtank Gallery a few doors down, run by the beloved North Beach artist Jeremy Fish.
As you continue ambling down Grant toward Columbus Avenue, impress your date with your local knowledge. You can casually mention that Caffe Trieste is the birthplace of both the Godfather movie and the flavored latte and point out that the Saloon is the oldest bar in the whole neighborhood. You can make a reference to the food wars made out of words when you pass by the Georgian restaurant Cheese Boat that had to change its name because of a Cheeseboat in New York City threatening suit—and also another SF food controversy with next-door taco shop El Farolito, which almost didn’t open its 12th location because of San Francisco’s ban on chain businesses.
But you’re not here for drama, at least not that kind of drama. So proceed onto Columbus Avenue from Grant, take in the lights and then hang a left on Broadway and a right on Kearny to arrive at your next destination: Tommaso’s Italian Ristorante.
Old School Dining at Tommaso’s
A meal at Tommaso’s on Kearny Street is like stepping into the living room of the Italian grandma you never knew you had. You should do it with your date while you still can, since the owners might be retiring soon. You’ll be greeted by co-owner Carmen Crotti, who is usually hard at work spraying down tables, seating customers and handing out delivery bags. She knows diners, many of whom are regulars, by their first names.
The Godfather Part III and Moonstruck movie posters don’t let you forget where you are—and neither do the original murals of the Amalfi Coast, painted on the walls when the joint first opened in 1935.
Tommaso’s doesn’t take reservations, but the wait is typically never more than 20 minutes on a weekend, and if you’re lucky, you’ll score one of the seven white wooden booths that line the wall. But sitting in the center line of tables has its own advantages—when you're cozy alongside other diners, there’s no saying what kinds of conversations might pop up in this ristorante that feels like a home for all kinds of San Franciscans.
Despite their irresistible name, skip the Coo-Coo Clams that come swimming in garlic broth, unless you want to topple your plus-one with your breath. But do partake in the wood-fired pizzas, which are the restaurant’s claim to fame. The pies are cooked in the same 900-degree brick oven they came out of in 1935.
“We’re the oldest pizza place on the West Coast,” Crotti said, who has been working there for half a century. Her family bought the restaurant from the previous head chef, Tommy Chin, who had worked for the family that opened it—the Cantalupos—and she continues to run it as a family business, working alongside her brother and sister-in-law.
The signature pies are chewy and crusty and go down well with the full-bodied Tommaso’s Red Blend. For dessert, try its take on a tiramisu, one that’s made with what tastes like vanilla wafers instead of ladyfingers.
“Everything was delicious,” said a customer clad in a black motorcycle jacket on his way out. “It was my first time here, but I’ll definitely be back.”
Live Music at Keys Jazz Bistro
Time your meal to stroll over to the Keys Jazz Bistro, a newly opened venue at 498 Broadway, for the 7 p.m. or 9 p.m. show (there’s also a late show at 11 p.m. Saturdays). You’ll walk through a large bar and lounge, where staff will seat you for the music. The intimate space makes you feel like you’ve been transported to an Upper West Side jazz club in the 1970s, minus the smoke: There’s a low stage, a blue velvet curtain undulating behind it and small round tables so close to the musicians it’s as if they’re playing only for you.
Table service is available for drinks and everything from light bites to entrees—not that you need to eat again, but you may be tempted by the dessert selection from local Italian bakeries. The crowd is remarkable for its enthusiasm and age range: 20-somethings sit alongside 70-somethings. You and your love interest will be tapping and bopping along before you know it, with plenty of dark cover if you want to get even closer.
With top-notch performances four days a week, Keys is new (and big) enough to still be undersubscribed, meaning you can play spontaneous and buy same-day tickets yet find a great seat.
Drinks at San Francisco’s Best Bar
If you can get past the mouthful of a name, Specs’ 12 Adler Museum Cafe at 12 William Saroyan Place is the platonic ideal of a bar, a respite from the outside world that somehow improves on it. The cozy watering hole, which most people simply call Specs’, emits a sepia tone at all hours and is one of the last bastions of reasonable cocktail prices in the city (a whiskey sour, for example, costs a respectable $7).
But it’s not the cheap drinks or even the warm vibe of the well-hidden courtyard bar that keep people coming back year after year since 1968. It’s the array of unusual ephemera hanging on the walls and ceiling, everything from nautical relics to walrus appendages. It’s the friendly yet boundary-respecting welcome of the bartender, who makes sure you’re going to have the most pleasant experience possible. It’s the diverse smattering of customers, strangers who somehow you seem to know already, all of whom are ready to talk—but not at all in a creepy way.
So depending on how your date is going, you can sidle up to the long bar to chat alongside others, or you can find a cozy table to sit just the two of you. The bar has plenty of room, even though more crowded on a Tuesday night than the sprawling Devil’s Acre bar on Columbus Avenue that abuts it. Locals keep local bars humming, and this one is quiet enough for talking, even with the light jazz music playing in the background that may prompt you to review the show you just heard at Keys.
Another item to bring the night full circle? Tees and totes for sale behind the bar made by Jeremy Fish, the artist whose gallery you walked by to start your evening. You’ve had the most San Francisco of evenings—mind-altering substances, fine food, music and drink—and now it’s time to bring it all (and your date) home.
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