I never get tired of exploring San Francisco, a sparkling white city on the bay that is just made for walking. I can spend all day meandering between neighborhoods as I climb up and down the steep streets. On a quick recent trip, however, with my college roommate Kendra, we decided instead of just wandering aimlessly we’d focus on four specific experiences, each a little different, but all having to do with either entertainment or educational and cultural enrichment.
Here is how I experienced San Francisco four ways — two that you’ve surely heard of and two that you likely have not.
1. Immersive Theater at The Speakeasy in Chinatown
Of the four experiences, The Speakeasy was so unique it quickly became my favorite memory from this trip. The experience is referred to as “immersive theater” meaning you are free to roam the venue as the scenes being acted out unfold around you making you feel like you are actually a part of the production and I had never experienced anything like it before.
A few days before the show I received an e-mail with an intersection to meet at in Chinatown and instructions for what to do upon arrival and also to dress in 1920s attire. Upon arrival, it was easy to see we were in the right location because pretty much everyone getting out of their Ubers or walking up was dressed in Gilded Era evening attire. Following the instructions from the e-mail we asked the person who fit a certain description where we could find a “good slice of pie” and from there we were directed to another character who gave us a sealed bag to store our phones in as well as directions on how to get inside the venue, which is in a basement under a room disguised as a Chinese laundry.
I loved that they took our phones because it meant we wouldn’t be able to get distracted by looking at them. For once, I’d be forced to truly experience something again. Upon entering the venue our first stop was the bar where we got an intro to some of the characters along with a few cocktails and later on soon ended up watching a vaudeville-type show with a six-piece band putting on an act. Afterward, we headed to the casino area, which quickly became my favorite place to hang out after a character taught me how to play craps. We were issued chips but weren’t playing for real money, just the fun of it. And during this time, characters kept wandering through, and we’d pause and listen to their dialogue or learn a crazy vaudeville dance or pick back up a storyline we’d first seen back in the bar and then they’d continue on to somewhere else in the venue and we’d go back to playing craps, and the entire experience was just so unique and fun and really I was able to just lose myself in the moment.
Another highlight was the one-way mirror into the showgirl’s dressing room. From here you could see the performers you’d just seen onstage, touching up their makeup, gossiping and occasionally full out brawling. Basically, the entire evening was a choose-your-own-adventure with really strong acting from than 80 different actors spread out across the venue that were following a 1,500-page script with dozens upon dozens of different storylines.
As all good parties must, this one came to an end with the Feds busting up the show and sending us all packing out the door. And in my case, at least, seriously craving more. Honestly, The Speakeasy is one of those shows you can see over and over again and not get bored: there are simply that many different storylines.
2. California Caribbean Dinner Party with Eatwith
Another experience I loved in San Francisco that I hadn’t known about prior to this visit was my dinner with Eatwith. The company describes itself as ‘Airbnb for food’ and the description works as the concept is to connect users with local chefs who offer immersive food experiences inside their homes. The result is a hyper-local dining experience where you don’t just get to dine like a local but you also get to experience their world for a few hours.
Kendra and I decided to try it out on this trip. Our host, Emillio Mesa, lived in a flat in the city and hosted a wonderful dinner party made up of California Caribbean cuisine. It was really fun to step into a local’s world for an evening. All day we had been walking around the city looking at all these amazing San Francisco row houses and I couldn’t help imagining what they must look like inside. And now I was being invited to dinner inside one thanks to an app — that alone seemed like a very tech savvy San Francisco thing to do. Mesa’s home was perched high up on a hill overlooking the city and had fantastic views from the wood-paneled windows. The entire place was charming and filled with art and our dinner table was set beautifully with a forest theme.
I also liked how Eatwith paired us with another two people for the dinner experience, which made it feel more like a proper dinner party. The other two guests were another two women and the five of us had a wonderful conversation that flowed all evening as we enjoyed Mesa’s unique cooking.
Mesa was born in the Dominican Republic but grew up in New York City before moving to San Francisco. His home country definitely influenced some of the flavors of his food, while others come from California. The menu began with some really awesome empanadas that were filled with ground turkey, lentils, tomatoes and mixed-olives and finished with a fantastic coconut cream adult drink-style dessert that comes from a traditional Caribbean Christmas recipe. It features sweet cream of coconut, coconut milk almond milk, cinnamon and rum that is served over ice with a large cinnamon stick. In between, we had a very good oven roasted chicken and shrimp dish with a homemade sauce made from mixed tomatoes, chickpeas, onions, garlic, cilantro, olive oil and red wine accompanied by Spanish yellow rice and a salad with greens from the local farmer’s market.
3. Exploring and Eating in The Mission District
The Mission District has undergone a massive transition over the past few decades, and while it was once a working class mostly Latin American family neighborhood, today it has completely evolved and is hipster central, filled with cupcakeries, taquerias, and vintage boutique shops. I choose to explore it because I wanted to see how gentrification, for better or worse, had changed this neighborhood.
I discovered as a tourist, The Mission is a fun place to just wander around and check out city views between lunch and dessert, which here should be eaten separately. For lunch, I loved Soulva, which is an industrial-sleek Greek sandwich spot. It is known for its rotisserie meat sandwiches, like the chicken sandwich that I ordered. There are also Mediterranean wines and salads, and I recommend sitting outside and people watching.
After lunch check out Dandelion Chocolate for dessert. At this shop, you can watch chocolate making in progress and then pick up some sweets from the counter, which are always rotating but include a decade brownie bite flight and an absolutely delicious dulce de leche bar. There was also a s’more treat with homemade graham crackers and marshmallows with chocolate ganache that was mouthwatering.
The Mission is also becoming known as a place for shopping. Most of the hipster boutiques and upmarket vintage shops are found along Valencia Street, which is home to both as well as a treasured local hangout spot Ritual Coffee. If you want more basic thrift stores then you can find those on nearby Mission Street.
4. Visiting Alcatraz
Alcatraz is one of those tourist attractions you just have to experience once, and so it became the fourth way I choose to explore San Francisco. And the trip to “the Rock” is well worth making. It begins with a 15-minute ferry ride that features really beautiful views back across to the city as well as the East Bay and Marin County. Once you’re on the island you’ll follow a tour that tells the stories of Alcatraz’s most notorious criminals in the cell blocks where they were incarcerated including Al “Scarface” Capone and George “Machine Gun” Kelly.
For me, the real highlight of the tour with Alcatraz Cruises was meeting a former inmate, William Baker, who was there signing his book, “Alcatraz 1259.” He was jailed for cashing fraudulent checks and had a penchant for escaping. So the federal Bureau of Prisons transferred him to Alcatraz to finish the final three years of his sentence. Hearing his story first-hand in the place where part of it occurred was powerful.