Considered the promised land by many Easterners during the mid-nineteenth century gold rush, the city by the bay doesn’t seem to have lost much in the way of prestige or desirability. People still flock to its temperate coastline, hoping to reap the benefits that all of North-Central California has to offer. Surrounded by valleys full of vineyards and technological promise, San Francisco will forever be rooted in its counter-cultural influence. The people of San Francisco seem to refuse to allow their city to slip from the forefront of progressive policy and inclusive civic structure, making its varied neighborhoods a destination for 21st-century prospectors with modified hopes, dreams, and aspirations. Now one of The United States’ most polished cities, San Francisco might very well be the manifestation of the American Dream.

Album: The Dandy Warhols – Thirteen Tales From Urban Bohemia
Book: On the Road – Jack Kerouac
Movie: Kiss Them For Me (1957)
Season: Winter

Coit Tower

1 Telegraph Hill Blvd

Everybody sees Coit Tower, but not many people actually venture up to the Mount Olympus of North Beach to check it out in person. Built atop Telegraph Hill in Pioneer Park, the tower was a posthumous gift of a well-respected socialite (aka a flapper with wealth and pedigree), who desired to “beautify the city” even from the afterlife. Its unpainted art deco exterior is impressive (if not befuddling) in its own right, but the fresco murals that line the interior might be the more exciting part. Built in 1933, construction on this tower served as one of the many American building projects that kept people employed.

The Castro Theater

429 Castro St

One of the last great surviving American movie palaces, the Castro Theater is almost a hundred years old and home to some of the most immersive screenings in The Bay. From silent films with a live orchestra to reruns of classic seventies and eighties date movies, there’s something for everyone at The Castro. The interior of the theater makes it almost difficult to concentrate on the screen, its design still stuck in the roaring twenties. The lively Castro neighborhood is a fun place to spend a night out, too, if you’re up for it.

Mollusk Surf Shop

4500 Irving St

A few minutes’ walk off Ocean Beach, this surfer’s surf shop has served as a sort of inspired mediator between surf culture and the San Franciscan ‘real world’ for a while now. With sister shops in Venice Beach and Silverlake, Mollusk is ready for beach bums of all kinds to walk through their door. Designer surfboards and ‘homegrown’ attire (they have their own label) give this place a rooted feel, while the travel photos and surf books will make you want to hop a plane to wherever. Mollusk sponsors several surf jamborees and is a true patron to the enduring art of coastal rock ‘n’ roll and throwback beachside DJ sets.


255 Columbus Ave

A bonafide cultural landmark of North Beach, this saloon may have served more drinks to more Beat generation authors and poets than anywhere else in the city. All that separates it from City Lights is Jack Kerouac Alley, and the king of Beat literature even has a drink named after him here at Vesuvio (it’s surprisingly fruity). Considering the incredible amount of rare and probably unseen photos that populate the building’s sacred walls, it’s worth buying a drink and giving yourself a tour. Our favorite is the black & white of a young Kerouac in his Merchant Marine uniform, ready to see the world. It hangs on the north wall of the lounge.

City Lights Books

261 Columbus Avenue at Broadway

More than just a free-thinking independent bookstore, this address is responsible for the publishing and dissemination of some of the most influential and polarizing words ever put to paper. Lawerence Ferlinghetti opened the place in 1953 and subsequently attracted the minds of poets like Allen Ginsberg, Gregory Corso, Frank O’Hara, and Diane diPrima, just to name a few. Famous for its ‘Pocket Book Series,’ City Lights was at the center of the epic struggle between free speech and censorship when the state department’s obscenity charge saw both Ferlinghetti and the shop’s manager arrested in 1957. Ferlinghetti, an accomplished poet himself, is still around, checking in on his shop, often unannounced, several times a week.

Bike or Hike The Presidio

The Bike Hut at Pier 40, Embarcadero rents some of the greatest bikes in the city

The labyrinth of trails that cut through the Presidio are, in a word, magical. Between gusts of cool saltwater breezes, expect a gentle blast of fresh eucalyptus scent as you peddle your way from the Golden Gate overlook to the promenade or by old abandoned military installations (the presidio housed military personnel until 1994).  We refuse to recommend one trail over another, but the Batteries to Bluffs trail, less than a mile long, is usually the first path down which we guide our guests.

Pier 7

Pier 7, Embarcadero

Not exactly an attraction, but if we were to show you around San Francisco, our trip would probably start (and end) right here. It’s a picture-perfect spot for a casual stroll out over the waters of the bay, or if the wind’s down, a good spot to spend the afternoon reading or mixing a playlist. The nearby ferry terminal is a great place to pick up a coffee or snack for the walk down Embarcadero, a sort of pilgrimage trek that, in our opinion, all newcomers to SF should walk with pride. A few piers down (in the direction of Fisherman’s Wharf), you’re about 75% certain to run into a few barking seals. Turn around to face the city for stunning views of North Beach and Coit Tower.

Parada 22

1805 Haight Street

Ok, ok… We know we’re the entire length of the continent away from Puerto Rico, but trust us, this place is for real. With only ten tables, you’ll spend your meal feeling like you’re dining amongst close friends, and the modest prices and bold flavors will send your head straight to the northeastern Caribbean. Amoeba Records and Golden Gate Park are a few steps to your left as you leave, the heart of the Haight-Ashbury neighborhood to the right. Not a bad little spot.

Decades of Fashion

1653 Haight St

Again, we’re going to lean towards the more orderly of your urban vintage clothing store options, and suggest one of the Haight’s landmark thrift shops. Every hanger in this store is organized not just by decade, but according to style and material popular from within that decade. Plenty of fitting rooms and an authentic feel to the place will make all the difference when you compare it to the area’s other shops. It can be a bit more expensive than its peer shops, but the clothes here are tried and true.

Palace of Fine Arts

3601 Lyon St

Located in the Marina District, The Palace of Fine Arts was built in 1915 for the Panama-Pacific Exposition and was so impressive that unlike other buildings designed for the occasion,  it was spared from demolition afterward. Its towering rotunda and classically-inflected pergola make its shade an idyllic respite from the busy Embarcadero a few blocks away. Another great spot to spend a lazy afternoon in the company of a freshly-acquired book from City Lights.

49(ish) Mile Scenic Drive

The route was originally created for the 1939 Golden Gate International Exposition in hopes that visitors would be able to see the highlights of the city in a single afternoon. The route that stands today marks a modified (and somewhat shortened) path through San Francisco, and the modern traffic patterns can make it tricky to follow from beginning to end. If you’re unable to commandeer your own vehicle, we recommend biking parts of the route piece by piece. Watch out for the hills and tram cars! Some of the route is more bike-friendly than the rest. If you make it across the Golden Gate you won’t be sorry!