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Three Perfect Days: San Francisco

Home to tech mavens, foodies, counterculture types and newcomers from all over the globe, America’s hilly, fog-shrouded Golden Gate is a city unlike any other.

Author Matthew Thompson Photography Erin Kunkel

The boat to Alcatraz

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DAY ONE | It’s almost unfair to call the Fairmont Heritage Place (1) a hotel. With its massive suites, exposed brick walls, ocean-view patios and fire pits, it feels more like a trendy loft co-op. While it’d be tempting to kill the day lounging on your private porch or digging through their 500-title DVD library, you lace up your walking shoes and throw yourself out into the city.

First, you head around to The Buena Vista Café (2), a local institution famous for its Irish coffees. You order the Dungeness crab omelet and marvel as the bartenders whip up drinks 30 at a time behind the long wooden bar. Don’t linger too long, though. You’ve got a boat to catch.

Reached via a 1.5-mile ferry ride, Alcatraz prison (3) stands like a crumbled castle above San Francisco Bay. Once home to the likes of Al Capone, George “Machine Gun” Kelly and Robert “Birdman” Stroud, it is now run by the National Park service. Former prisoners and guards narrate the self-guided audio tour, highlighting everything from the bullet holes in the walls to the beaten lawn of the baseball diamond.

Back on the mainland, you take a left down Embarcadero Street and walk to the Ferry Building (4). Once a transportation hub, this brick colossus has been converted into a marketplace for artisan foodsellers— check out Acme Bread Company for sourdough and Cowgirl Creamery for gourmet cheese— and a jaw-dropping farmers market on Tuesdays, Thursdays and Saturdays. You forage together a fresh picnic lunch and eat staring out at the waterfront.

Now it’s time to burn those calories. You head through Levi’s Plaza to the Filbert Street Steps (5), an epic staircase climbing to the summit of Telegraph Hill, and soak up the gardens on either side—a brilliant mix of banana plants, azaleas, bamboo groves and agave that often play host to flocks of wild parrots. At the top you catch your breath in the shadow of Coit Tower (6), a stone observation deck with 360-degree views of the city, from the pyramidal Transamerica Building to serpentine Lombard Street. (Mercifully, there’s an elevator.)

Next, head down to Grant Avenue. Running north to south, this street bisects two of San Francisco’s most storied neighborhoods: North Beach and Chinatown. In North Beach, check out the quirky boutiques and inhale the tantalizing aroma of Italian bistros. Be sure to drop into Vesuvio (7) for a cheap drink and a stiff shot of Beatnik culture—Jack Kerouac and Allen Ginsberg used to hang out here, and the walls are crammed with pictures, poems and scribblings they left behind.

Below Columbus Street, Grant transforms. Gone are the tiny shops and clothiers; in their place are the markets, importers and dim sum restaurants of Chinatown (8). As the street begins to rise toward Nob Hill, be sure to pop down a few of the alleys, where working spice shops and junk stores replace the tourist emporiums along the main drag.

Back at the hotel, it’s time to freshen up for dinner, but don’t spend too long on your outfit. Where you’re going it won’t matter. Opaque (9) is a gourmet restaurant with a twist: It serves its meals in pitch darkness. It’s messy, but the deprivation of one sense enhances the others in ways you never thought possible. With fantastic cooking from head chef Michael Whang and phenomenal service from the waitstaff (all of whom are visually impaired), it’s a dinner worth remembering.

You’ve got one more stop to make before bed. Catch a cab over to First Crush (10) for a little taste of Napa Valley. Ask the knowledgeable waitstaff to assemble you a custom flight (a lineup of mini glasses) from the 500-plus-label wine list. You savor a variety of jammy reds or aromatic whites before heading to bed.

3 Responses to “Three Perfect Days: San Francisco”

  1. Jean Nelson-Dean Says:
    April 11th, 2011 at 11:31 am

    We just returned from our second trip to San Francisco with our kids. I wish I had seen this article before we left. Though we did many wonderful things, I would have had a few more great ideas. I am saving it for next time. What a great city! Everyone loves it from the tween, teens, and my husband and I.

  2. Sheila Krotz Says:
    May 4th, 2011 at 10:20 pm

    I love the 3 day series, but I felt as though you missed the mark with your recommendation of the Buena Vista Cafe; it is not well liked by the locals and there are so many better places to eat in SF! You did make a good recommendation with Beretta, though.

  3. sharon waller Says:
    January 27th, 2015 at 2:29 am

    You forgot to mention Boudin Bakery and Ghiridelli Square, a must when in SFO. Try a side trip to the Walt Disney Family Museum at the Precidio. A little expensive but well worth it for the Disney in us all.

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