Three Days in San Francisco

Of course, it wasn’t until I moved away from San Francisco that I truly appreciated the splendor of what I had at my doorstep. It’s a city of unbounded creativity and unforgettable beauty. A city as dedicated to its baseball team as it is to eating locally, organically, and deliciously. And a city that has grown up through gold rushes, earthquakes, and world war efforts, weaving a rich history along the way.


Thanks to my current displacement from the San Francisco Bay Area, my home base has instead become one of my favorite long weekend destinations—the perfect getaway for travelers who take their beautiful cities with a healthy dose of eccentricity. Foodie or outdoorsman, hippie or hipster, there’s a little something for everyone here.

So pack your bags. And be sure to wear some flowers in your hair.


Sittin’ On The Dock Of The Bay

As the California Gold Rush took hold of the western United States, San Francisco—a small coastal city established by Spanish colonists in 1776—saw its population swell from a mere 1,000 people in 1848 to almost 25,000 a year later. And with nearly a century left before the Bay and Golden Gate Bridges would be completed in 1936 and 1937, the ferry boat became the sole method of transport to San Francisco for commuters, travelers, and prospectors from the north and east.

Today, the Port of San Francisco has become a gathering place of another sort. While the boats still come and go, the Ferry Building Marketplace—a humming collection of restaurants and artisan food stalls—is both a destination for food-loving visitors and a part of everyday life for San Franciscans. And it’s here where your journey begins, assembling a picnic with the help of Boccalone SalumeriaCowgirl Creamery, and Acme Breadand renting a top-notch bike from Ferry Building Bike Rentals.

People In Motion, People In Motion

In 1989, the Loma Prieta earthquake tore through the San Francisco Bay Area, killing 63 people and leaving thousands homeless in a matter of seconds. Among the major structural casualties was the Embarcadero Freeway, a double-decker eyesore that had dominated the city’s waterfront since 1957. But in 1991, the freeway’s demolition paved the way for the revitalization and redevelopment of the Embarcadero—the first leg of today’s bayside bike ride.

Pedaling north and west from the Ferry Building will bring you to Fort Mason, the primary port of embarkation for World War II servicemen shipping out to the Pacific, and Crissy Field, a former military airfield-turned-perfect picnic area. Just don’t turn back before reaching Fort Point, the lighthouse and fortification that has guarded the Golden Gate Strait since 1861.

Still have any leg strength? Hop on the nearby California Coastal Trail, which connects the Golden Gate Bridge to historic gun batteries, stunning bridge viewpoints, and the unbeatable sunset scene at Baker Beach. It’s also well worth the few extra miles to visit Land’s End and the Sutro Baths, the lovely ruins of an ocean pool aquarium and public bathhouse developed by Mayor Adolph Sutro in 1894.

Lazy Bears, Stare!

No doubt you’ll have worked up an appetite, so it’s a good thing you’re in one of the United States’ foremost culinary capitals. Curious to try something truly unique? Snag a ticket for one of the two seatings at Lazy Bear, where you’ll join a lively communal dinner party featuring outstanding modern dishes (3416 19th Street). Looking for something a little more classic? The heavenly roast chicken for two at Zuni Café in Hayes Valley is a San Francisco legend (1658 Market Street).

The Big Friendly Giants

There are ballparks and there are ballparks. Candlestick Park, the windswept behemoth that housed the San Francisco Giants from 1960 until 1999 was the former. AT&T Park, the team’s picturesque home since 2000, is the latter. Situated on the water’s edge south of Market Street, there’s no better place to spend a Friday night—watching the greatest team in baseball with a stunning backdrop view of the artfully illuminated Bay Bridge (24 Willie Mays Plaza).

Fort Point

Golden Gate Bridge

Baker Beach

Baker Beach


Jane Says

On the morning of April 8, 1906, San Francisco was hit by one of the worst natural disasters in American history—a catastrophic earthquake that killed an estimated 3,000 people and left half of the city’s 400,000 residents homeless. This morning’s destination? Pacific Heights, the beautiful hillside neighborhood where many of San Francisco’s elite rebuilt their homes.

After ogling the mansions lined up along Broadway—and enjoying views you’ll likely never be able to afford—console yourself at Jane, where the wonderfully bright atmosphere is matched by its delicious breakfast sandwiches (2123 Fillmore Street).

Your Mission, Should You Choose To Accept It

Head south of Market Street for an afternoon near San Francisco’s birthplace—the Misión San Francisco de Asís, more commonly known as the Mission Dolores. Founded in 1776 under the direction of Father Junipero Serra, this adobe mission is the city’s oldest building, as well as California’s oldest original intact mission. And it’s also the namesake for one of San Francisco’s most vibrant and diverse neighborhoods.

Make your first stop in the Mission District at La Taqueria, a decades-old institution known for its positively killer burritos (2889 Mission Street). But the delicious cheap eats don’t end there. A rotating selection of seasonal pies awaits at Mission Pie (2901 Mission Street), while Bi-Rite Creamery produces the city’s best small-batch, homemade ice cream (3692 18th Street).

Need some digestive assistance? Grab a cup to go at the original Philz Coffee (3101 24th Street), and spend the afternoon grazing on the sunny hillsides of Dolores Park (18th and Dolores Streets). Nowhere is San Francisco’s unique character on better display than this 14-acre expanse, where a diverse mix of families, hipsters, sunbathers, and hippies gather to enjoy one of the city’s best skyline views.

Flour Children

It’s no easy task narrowing down your dinner options in the Mission. Whereas Californios offers a Mexican-inspired tasting menu that is both seasonal and refined (3115 22nd Street), Foreign Cinema serves big flavors in an unmatched atmosphere (2534 Mission Street). But tonight you’re headed to flour+water, chef Thomas McNaughton’s showcase of homemade pastas and stellar local ingredients. No reservation? Join the crowd that lines up before dinner service each night, and you just might get lucky (2401 Harrison Street).

Not ready to call it a night? Grab a stool down the street at the James Beard-nominated Trick Dog, where you’ll choose from an inventively presented menu of even more inventive cocktails. If it’s offered, don’t miss the Pantone 7621, a tasty blend of bourbon, Combier, kummel, beet, ginger, and lemon (3010 20th Street).

Mission Dolores Basilica

Dolores Park




Purple Hayes

Begin your morning in the Western Addition, San Francisco’s first multicultural neighborhood developed at the turn of the century. Just north of the Panhandle—the long, narrow park sandwiched between Oak and Fell Streets—some of the city’s best brunch dishes await you at NOPA, from custard French toast to butter-basted farm eggs (560 Divisadero Street).

Stroll off your breakfast several blocks eastward in Hayes Valley, another neighborhood that gained new life following the 1989 earthquake. It’s also the site of the most grueling portion of the annual Bay to Breakers, as tens of thousands of costumed runners gasp their way up the Hayes Street Hill. But this morning, you’ll begin your walk among the Painted Ladies in Alamo Square, strolling downhill to browse the boutiques of the Hayes Street corridor. With perfectly soft original tees at Marine Layer, adorable travel accessories at Flight 001, and an impressive denim selection at Azalea, you’ll have plenty to keep you busy all morning (Hayes Street between Laguna and Gough Streets).

Parks And Recreation

Although it sees nearly 13 million visitors each year, Golden Gate Park quickly makes you forget that you’re in a city of more than 825,000 people. This thousand-acre expanse is a joy to explore and an even greater joy to get lost in. You may end up at the front door of the breathtaking Conservatory of Flowers, or reliving the Summer of Love on Hippie Hill to the east. Just be sure to make time for the California Academy of Sciences, one of the largest and greatest museums of natural history, or the de Young Museum, the host of such wonderful visiting art exhibits as Johannes Vermeer’s “Girl with a Pearl Earring.”

Last Tonga In Paris

As the evening fog begins to roll in, snag a seat at Rich Table, the brilliant new venture from chefs Evan and Sarah Rich (199 Gough Street). The menu is exciting and ever-changing; the atmosphere warm, rustic, and inviting. And you’re only blocks away from a pre-game at Biergarten, a wonderfully entertaining San Francisco interpretation of the traditional German beer garden (424 Octavia Street, be warned—they close early).

But really, there’s no better place to bring this long weekend to a close than the Tonga Room & Hurricane Bar, a landmark of island kitsch in the basement of The Fairmont (950 Mason Street). The drinks have names like the Bora Bora Horror, while live music is played on a thatch-covered barge floating in a small indoor lagoon. Need I say more?

Alamo Square

Nob Hill


A Few Notes

You may notice that there’s no mention of Alcatraz, Fisherman’s Wharf, Pier 39, or Haight-Ashbury in this post. That was on purpose. Trust me, your time is better spent elsewhere.


TITLE: The Golden Gate Bridge | FRIDAY: Fort Point; the Golden Gate Bridge, from the California Coastal Trail; Baker Beach; Baker Beach | SATURDAY: Mission Dolores; Dolores Park; dinner at Flour+Water | SUNDAY: The Painted Ladies in Alamo Square; a cable car on Nob Hill.

I’m Maura O’Brien, a professional writer & editor, amateur photographer, and lifelong adventurer based in Portland, Oregon. The Long Weekender is my travel home—a blog that both documents my most memorable travel experiences and (hopefully) helps you make the most of your weekends. Looking for budget-friendly suggestions for where to eat, drink, and play during your next jaunt in the United States or abroad? You’ve come to the right place.

Tips? Comments? Feedback of any kind? Don’t hesitate to contact me at

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