5 Unique (and Cheap!) Date Ideas in San Francisco

Kevin and I were recently in San Francisco to celebrate our friend Brandon’s landmark 40th birthday. It was a pretty wild weekend between his birthday festivities and the fact that it was gay pride weekend — pretty much a national holiday in these parts! But despite all this, Kevin and I were able to fit in some quality time together.

We love getting back to the Bay area — getting in our stair master workout climbing all those hills as we explore neighborhoods. Who needs a gym?

While the city remains an obscenely expensive place to live ($15 million for a 3 bedroom condo, anyone?), there are still plenty of fun and cheap San Francisco date options. Below are our top 5 date ideas — mostly off the main tourist track.

5. Join the Mob of Food Instagramers for a San Francisco Treat

Visiting one of San Francisco’s buzzy food hot spots is a must. Though, I gotta admit, it’s sort of like mentally preparing for a trip to Disneyland. There will be lines! But just think how much extra time you’ll get to bond with your date. Or you can be like Kevin and read a book to pass the time. You be you Kevin! Our first date stop was to try out Boba Guys. A friend who lives in San Francisco recently recommended this busy local chain, which specializes in tea drinks with super squishy tapioca balls.

San Francisco is where it all started. Though, now you can find outposts in both New York City and Los Angeles. So you might be thinking, what’s so different about this boba tea? Well, it’s all in the ingredients. Boba Guys avoids the typical powder mixes and use loose-leaf tea, real fruit and a range of premium milks in their drinks. I ordered the Korean Banana boba with almond milk — a specialty drink that I pretty much downed in 5 minutes. It’s all about customization here with options to adjust the sweetness level on most drinks or skip the sugar completely. But where’s the fun in that? If the weather is nice, head over to Mission Dolores Park with your boba to see San Francisco out in full force or join the line for ice cream nearby at Bi-Rite Creamery.

4. Take a Hike Through Lands End

Like the name of the hike suggests, Lands End trail is at the very far end of San Francisco. Again, Kevin and I love to keep active. We couldn’t have asked for a better way to catch up with friends while taking in the gorgeous scenery.

The network of trails takes you along the long abandoned Sutro Baths (once a public swimming pool), caves and a labyrinth. It’s a fantastic way to celebrate a warm(ish) San Francisco day. And after a few hours hiking here, we don’t feel so guilty about all those cookies we ate at the farmer’s market!

The trail is just over 3 miles and is mostly flat, so it’s a great option if you have friends or family joining with a variety of athletic abilities.

3. Watch a Classic at the Castro Theater

Built in 1922, the Castro Theater is a San Francisco institution. The 1,400 seat theater is home to many of San Francisco big premieres including the 2008 Academy Award-winning film Milk and more recently the premiere of Netflix’s reboot of Tales of the City based on Armistead Maupin’s novels. You don’t have to look far to see where Maupin got his inspiration for his novel’s quirky characters. On this past visit to the Castro, we sat next to someone dressed in a wizard costume, another person with a giant purple hula hoop and a group of guys wearing nothing but bathrobes.

The Castro Theater plays a rotating line-up of films — from classic to indie sleepers. We highly recommend going for one of their famous Disney sing-alongs. Last year, we joined in their Little Mermaid sing-along. In most cities, this sort of thing would be packed with kids. Not so much the case here — where a majority of the audience were adults dressed as mermaids (or more as “mer-men”!). On this trip, we checked out a hilarious rom-com called Simple Wedding, part of the Frameline Film Festival, about an Iranian-American woman’s quest to find love and appease her parents. Playing films from across the spectrum of independent film, the Castro Theatre is one of the last picture palaces left in the San Francisco area.

2. Be Part of the Show at Piano Fight

I’ve had Pianofight bookmarked on my phone for several years — but it wasn’t until this past trip that we checked out this tiny performance space hidden inside a bar in the gritty Tenderloin. The venue features mainly local San Francisco artists and shows that run the gamut from world-premiere plays to sketch comedy acts. We went to see one of the strangest, yet entertaining shows called The Infinite Wrench, presented by the SF Neo-Futurists who describe themselves as “a collective of wildly prolific writers/directors/performers who create theater that’s a fusion of sport, poetry and a living-newspaper.” The show consists of 30 bite-sized plays in just 60 minutes with their order determined by the audience. Each week, the ensemble dishes out new plays (written by them) ranging from the personal to the political to profoundly WTF weird. Each piece is inspired by actual experiences of the performers.

Pianofight has shows nearly every night of the week with most tickets running just $15-18 per person. Yes, I love a cheap date night! There is also a full dinner menu (though you can’t bring the food into the theater) as well as a bar (and you can bring your drinks inside).

1. Soak in a Japanese Hot Bath

“A Japanese bathhouse in the Tenderloin?” Kevin asked, after hearing I booked us 2 spots at Onsen Bath. Okay, he definitely was a little skeptical but I have to admit, it did sound a little sketchy. But upon walking inside, you’ll be completely transported from the Tenderloin to a traditional Japanese bathhouse that could be in Tokyo.

We visited Japan a few years ago, and one of our favorite things was the onsen ritual. In fact, we even soaked on a recent trip to Queenstown, New Zealand. There are a variety of sessions you can book, but we recommend the “early soak,” a 1-hour session beginning at 10 AM that costs just $23 per person. Inside you’ll find a 4-foot soaking pool, a dry redwood sauna, a steam room and cold plunge shower (where I may have screamed and jumped up and down after learning this fact!).

The onsen offers more extensive packages, with some even including meals, sake and tea at their on-site restaurant. They also have massage and acupuncture sessions. The space is co-ed most days and swimsuits are required. They offer men-only days on Wednesdays and women-only on Thursdays (between 11 AM – 3:30 PM). And swim suits are optional.

Have more than a weekend in California? Then I suggest doing a classic road trip to the redwoods or spoiling yourself silly in Napa wine country. Or if it’s rainy and wet in San Francisco, check out our itinerary of the best rainy day activities. With all these San Francisco date ideas, you’ll need a month or 3 to explore!