a couple walking on the streets of san francisco usa

A stark contrast in highs and lows, the juxtaposition between consumer culture and street life is more evident in Union Square than anywhere else in San Francisco. The city’s highest concentration of theater, shopping, galleries and hotels lies within a walkable (but deceivingly hilly) four-block radius of the Plaza. In contrast, the Tenderloin, a diverse and sometimes troubled adjacent neighborhood, intermingles with the glossy shopping district to form an ill-defined and vibrant nucleus. With the boundaries blurred between world class comforts and gritty street vibes, Union Square holds a little for everyone, whatever your poison. 

To many people, the iconic image of Union Square conjures up a cast of Hitchcock characters — overdressed bellmen and servers waiting on perfectly coiffed ladies who lunch (The Rotunda) while male counterparts deal in dimly-lit dining rooms over rare steaks, lobsters and Scotch (The Redwood Room). Those in search of Murano glass gift shops, cable car photos, and classic film clichés are in luck; amidst all the technology and change, old San Francisco still stands. 

You can get your fix of red velvet nostalgia at The Starlight Room, an old-school lounge with expensive drinks and a knockout view. For an updated take on the bar as perch, check out the elevated patio at Jones overlooking Geary Street below.

The beauty of Union Square is there’s no one way to do it. Dinner and a show can mean a fancy Vietnamese French fusion meal at Le Colonial followed by a blockbuster Broadway production, or a salty, cash-only bowl of pho at Tu Lan before a DJ set at Mezzanine or Monarch.   

It’s a true cosmopolitan center where two communities collide, lending a little character to the polished commercial ‘hood. Defining where one neighborhood ends and another begins is a blood sport in San Francisco (like arguing the merits of Four Barrel vs. Ritual Coffee Roasters). Heated debates are rarely settled, thanks to a lack of geographic and administrative boundaries. While the Tenderloin extends farther west toward Civic Center, Union Square and the TL are one and the same for at least a handful of blocks.

Because of its shared location, visitors to downtown San Francisco are often surprised by the prevalence of homelessness and mental illness. While most street characters harmlessly go about their own business, it helps to be aware of your surroundings to prevent opportunistic petty crime. It isn't worth worrying about, but it is worth noting.

Despite its obvious flaws, the Tenderloin brings a lot to the table, and the neighborhood’s diversity shines brightest in its food scene. Affordable Indian and Southeast Asian fare sustains working class locals and savvy travelers. Hipsters, art students, and service employees contribute to the creative vibe and buzzing Tenderloin scene. Though run down, many of the area’s historic apartment buildings boast rooftops where the young, broke, and beautiful gather after last call. 

The nightlife is vibrant, and some of the city’s best. Hopping in a rideshare or walking with a friend will help you navigate the sketchier blocks on your way to that perfect dive bar. San Francisco isn’t exactly a clubbing mecca, but its abundance of artisan cocktail bars makes up for it tenfold. 

The granddaddy of all speakeasies, Bourbon & Branch, opened way back in 2006 and set off an avalanche of natty password-protected bars within bars (within bars, within bars). Farm to table, deliberate cocktails abound in Union Square, many without a need for secret passwords, side doors or moustaches. Rye, Tradition, and Local Edition are all good options to get you started.     

First Thursday, a monthly gallery walk, also brings together a crowd of well-heeled art personalities ranging from quirky collectors to ambitious young artists looking to make connections and scam on free booze. Most of the participating galleries are located on Union Square, with a few edgier outliers like 1 am and Luggage Store representing more urban work. Start early and hit the streets or stick to one building full of dealers (like 49 Geary) and work your way down. Most galleries only stay open late on the first Thursday of each month, though it’s worth checking out the openings calendar for other evening events if your trip doesn’t coincide with the art walk.    

To clothes horses the world over, shopping at Union Square is a rite of passage. Anchored by Saks, Neiman Marcus and Macy’s, the swanky public plaza is the city’s epicenter of high-end retail. Luxury boutiques like Tiffany, Bottega Veneta, Hermes, and Louis Vuitton dot the surrounding blocks, giving wealthy tourists and tech moguls a place to unload their excess cash.

Forgot your Amex black card? No sweat — a walk towards Market Street offers a little more approachable pricing. Get a last-minute outfit from fast fashion megastores (H&M, Uniqlo) or check out the Westfield Center mall for familiar brands (Abercrombie, Superdry, J. Crew) and a killer food court (as far as food courts go).

Check out exclusive San Francisco collections at the Levi’s flagship store, or get a pair of customized Chucks at Converse to take home something special without a total splurge.

Overall, staying in Union Square puts the city’s best at your fingertips. A central location makes grabbing a cab or public transportation a breeze when exploring other neighborhoods (or calling it quits when your heels are no match for the legendary hills). The bustling city center offers nightlife, shopping, and entertainment for every taste. Choose to curate your experience or simply hit the streets and go with the flow.