Cole Valley/Upper Haight/Golden Gate Park
These three places could not be more different from each other, and yet, are all within close proximity, making for the perfect weekend adventure. Cole Valley is a little village where you’ll mostly venture for eating and drinking, the Upper Haight, or as the tourists call it “Haight-Ashbury,” is home of the Summer of Love and the Grateful Dead and still represents all of that 50+ years later. And at the end of Haight Street is where the iconic Golden Gate Park begins, spanning over 1,000 acres of museums, gardens, lakes, and history.
Stay: Like so much of San Francisco, this area is very residential, but there are a few good housing options, starting with the Stanyan Park Hotel, a boutique Victorian hotel with San Francisco charm. If you’re looking for something with more of a Haight-Ashbury hippie vibe and don’t mind creaky floors and other quirks, then you’ll love the Red Vic, “an experimental hotel” that doubles as a community space with lectures, art shows, and live music.
Breakfast/Lunch: Haight Street is full of quick counter-service options; our favorites are Slice House for great pizza, Street Taco for a stellar tostada salad, and What the Cluck for Thai chicken and rice. For a more leisurely brunch, the romantic back garden at Zazie, an adorable French-inspired bistro, is the best choice, though the wait can sometimes be a bit long.
Do: You can’t go to Haight Street without spending a little time exploring the shops. Whether you’re looking for vintage clothing, expensive sneakers, a new bong, or something tie-dye, Haight Street has it all -- including a cannabis dispensary if that’s your vibe. And since you’re there, you should also take a picture in front of the Grateful Dead House at 710 Ashbury Street where Jerry Garcia and other band members lived from 1965 to 1968.
The other must-explore area is Golden Gate Park. You could spend a week wandering around this urban park that was once just sand dunes and still not see everything, but highlights include: the California Academy of Sciences, which is among the largest museums of natural history in the world (go on a Thursday night for the 21+ party with cocktails and DJs); the de Young Museum, a fine arts museum that usually has great special exhibitions (the Harmon Observation Tower, which has 360 degree panoramic views of the city is free, as is the sculpture garden -- be sure to find the Turrell Skyspace, a walk-through meditation space); the Japanese Tea Garden, the oldest public Japanese garden in the U.S.; and the Conservatory of Flowers. Walking around Stow Lake and up Strawberry Hill (the highest point in the park) is a fun, mellow hike, and you can also rent row boats and pedal boats, an experience we find is even better enjoyed if followed by a beer at the Boat House.
If you dine in Cole Valley, find The Sword and the Rose, a “spiritual and metaphysical” shop hidden in a courtyard where you can shop for incense, crystals, and get your tarot cards read.
Dinner/Drinks: There are two bars that are must-visits on Haight Street: The Alembic, which pioneered the craft cocktail movement in San Francisco, and Aub Zam Zam, a dimly lit Persian-inspired bar that’s been around since 1941 and is famous for its martinis. For dinner, if you didn’t hit Zazie for brunch, then be sure to go now (the coq au vin is divine), or if you’re in the mood for delicious, upscale Mexican, Padrecito is the spot. The food and cocktails are both exceptional.