Sep 16, 20215 min read

We LOVE San Francisco!! 2021 Labor Day Weekend Trip Report

In my late 20s (after I started working at Google), I learned about Burning Man. I heard that it’s basically one giant party in the Nevada desert. There were no rules: you can wear clothes (or not), you can bring food and trade with others (or not), you can shower (most likely not). Apparently this is the Silicon Valley techie’s way of “living off the grid” for a week.

[It’s called “Burning Man” because there’s a giant statue of a man, built with a wood frame. At the end the week they set the “the man” on fire as a symbolic middle finger to corporate America, or at least I think that’s how the story goes]

Later on, I had many friends who went to Burning Man. There were intricate preparations in place: when to strike when the tickets go on sale, whom to camp with, what to wear (somehow there are costumes involved?), what to share with the community, and more.

Never once in the conversations did the festival of seemingly lawlessness appeal to me. What DID appeal to me, was the exodus of all the people out of SF and its surrounding areas.

When Burning Man did happen (it was canceled in 2020 and 2021 due to Covid), the city of San Francisco, and its surrounding neighborhoods became…. Quieter. With all the ragers and bangers gone, there was an abundance of parking, and instead of waiting in lines for brunch, one would literally waltz in at 10:00 am and score a table for 4. I know, because I did this.

Starting in 2018, Ben and I started fulfilling the dream of spending Burning Man/Labor Day weekend in SF. Our first year we scored a little Airbnb in Pac Heights/Cow Hollow, walking distance to Union Street and all its great restaurants, including my personal fav, Le Boulangerie. With a toddler in tow (A was 1½ years old), we literally strolled in on Saturday, got food, and enjoyed an amazing breakfast. We also walked all the way down to Fort Mason, saw the Golden Gate Bridge, meandered, before coming home on a Cable Car. It. Was. Incredible.

Year 2 we found ourselves in outer Noe Valley, at a kids-friendly Airbnb on 30th Street. We walked EVERYWHERE - to dinner. To ice cream, to the upper Noe Valley Playground everyday.

We skipped this tradition in 2020 because, well, you know.

Determined to return in 2021, this year I started making reservations in May. We found an amazingly spacious pad, this time in the outer Mission District (in the gentrified area). We walked to the Franklin Square Playground every day, we walked to Mission Dolores Park TWICE, we walked to Valencia for Smitten Ice Cream. Kids loved the adventure, we ate ALL the food.

Did I mention how good the food is in SF? On this particular sojourn, we visited Flour + Water with the kids (yes, they have kids’ pasta, which is basically tube pasta soaked in butter, we literally had to get 2 servings because kids tore through the first one). We also stopped by fan favorite Tartine Manufactory for breakfast (reservations were hard to come by) and brought home a bunch of pastries for the next day. Ben LOVED his almost daily lattes from Sightglass Coffee. Ben & I even enjoyed a date night at “Al’s Place,” which was still buzzing after its recent Michelin One Star win.

So how do you plan these trips, Merry? Glad you asked! Here are some tips to get started:

Though Ben and I are partial to fancy hotels (my personal favorite is the St Regis right next to SF MOMA), Airbnb is probably the more practical lodging option when traveling with young children. In our case, I literally scope out each Airbnb and see what’s in the surrounding area: Which restaurants can we walk to? What coffee shops? And most importantly, WHERE ARE THE PLAYGROUNDS? I also like it when the airbnb is close-ish to a busy street (say, Mission Blvd, or 24th Street), but not actually ON the busy street.
Focus on ONE neighborhood at a time. San Francisco is a big city with lots to offer. You could try to do it all and be physically and emotionally exhausted, OR, you can pick a great neighborhood and truly live like a local. Go to the local coffee shop (not Starbucks), check out the bakery in the corner. Almost every neighborhood has an ice cream shop. :) For the most recent trip, we were staying in/near the Mission, and there are literally hundreds of murals in the neighborhood. We’d stop at each one, and observe the mural and what we think it wanted to share, or is it a nice picture that someone drew. There’s SO much to see, I can’t say we’ve ever run out of stuff to do in a particular neighborhood
What gives you light/energy? Do THAT. Do you enjoy museums? If so, plan your trip/stay around the museum/arts district. Do you enjoy swanky shops? If so, maybe Pac Heights/Nob Hill is your speed. In our case, our mutual passion is FOOD. As mentioned above, I’ll literally scope out the restaurant scene before booking the Airbnb. What would enrich your soul? Do that and stay someplace that makes it super easy.
Optional, but if you like having structure, plan ONE major outing during your stay. Our first visit to SF, the major outing was to see the Golden Gate Bridge. So we did -- we actually walked through the Marina to Fort Mason, grabbed coffee then walked all the way down to the Yacht Harbor, before returning via Cable Car. Year 2 we spent the day at The Exploratorium, which was exhausting but SO worth the visit. This year we spent most of Sunday at the Bay Area Discovery Museum and my only regret was we waited this long to visit. It’s amazing in every way.
Plan for some downtime. City living can be really fun and exciting, but it can also be a lot (especially for kids). Plan about a 2 hour “downtime” each day to give everybody a break. If your kids still nap, the nap time is a natural downtime. Otherwise maybe they could read, or even watch their tablet for a bit. Overstimulation is real.
Finally - book a babysitter! Plenty of good ones on Urbansitter. Or, if you already have a regular babysitter, ask if they would be willing to come up to SF for the afternoon/evening. In our case, one of our regular sitters was already planning to be in SF that weekend and she babysat for us for 4 hours, which was glorious for us, and didn’t interrupt her birthday weekend plan. It was a win-win.

Next year, I think we’ll plan our trip around visiting the Golden Gate Park and eating ALL the good food in the Sunset/Richmond. Our flagship activity would probably be visiting the SF Zoo, unless we just decide to spend an entire day at Golden Gate Park. The good news is, the City is literally our oyster.

In the years to come, I hope to spend weekends in Chinatown/Little Italy, Hayes Valley, or maybe near the Ballpark. The options are endless. If it works out, I’ll get to spend the next 10 Labor Day weekends with my boys in San Francisco, and that would literally be my dream come true. <3

What are your family long-weekend traditions? What would be your dream come true? Share with us in the comments below!