Romantic Things to Do in San Francisco for the Holidays

1. Run (or Walk) in the National Ugly Sweater Day Virtual Race

December 12th | $20

Celebrate National Ugly Sweater Day on December 19th by joining this virtual race. Whether you run, walk, or jog, you can choose your distance (1 mile, 5K, or even a marathon) and complete it anywhere you like. It’s a great way to stay active and do some good—15% of the registration fee supports Feed My Starving Children, a nonprofit fighting hunger.

For $20, you’ll get a race bib, medal, and the satisfaction of contributing to a good cause. Throw on your favorite ugly sweater, lace up your shoes, and make this a date to remember.

2. Peter Pan Pantomime

December 14th-29th | $17-$68

Catch a fun and quirky take on the classic Peter Pan story in this British-style pantomime. Filled with over-the-top humor, audience participation (don’t forget to boo the villains!), and even flying candy, it’s a playful twist on a holiday theater night.

Join Peter, Wendy, and the Lost Boys as they take on Captain Hook and his pirates. If you’re looking for a lighthearted evening, this show is perfect for some laughs and holiday cheer.

3. Holiday Cookie Workshop

December 12th | FREE

Nothing says "holiday fun" like decorating cookies together. On December 19th at 4 PM, head to a Holiday Cookie Workshop where you can don your ugly sweater, decorate cookies, and get into the festive mood. It's a simple, laid-back way to spend an afternoon, and you might even pick up some ideas to use at home.

4. “Winter Wind” Choral Concert

December 22nd | $25

If you’re in the mood for something different, check out Winter Wind by Ragazzi Continuo. This choral concert combines haunting winter-themed songs with lesser-known holiday carols. The performance is emotional and unique, blending cold, ghostly themes with the warmth of seasonal music.

It’s an intimate and special experience—perfect if you and your partner enjoy live music and want something more low-key for the holidays.

5. Holiday Movie Trivia

December 17th | FREE

Love holiday movies? Test your knowledge at Holiday Movie Trivia Night on December 17th at Dave & Buster’s in Daly City. From Home Alone to Elf, this trivia night covers all the classics. It’s interactive, competitive, and full of laughs.

Play as a team, answer questions through your phone, and see if you can climb the leaderboard. Plus, there are prizes for the winners. It’s a great way to have some fun together while celebrating your favorite holiday flicks.

6. Let’s Glow SF

December 6th-15th | FREE

Photo credit: Let's Glow SF

Head downtown for Let’s Glow SF, the biggest holiday projection event in the country. From December 6–15, buildings in eight locations will light up with stunning animated displays by artists from around the world. Walk around with your partner, grab some free hot chocolate, and enjoy the festive vibe.

For an extra special night, check out the Glow on Front Block Party on December 13th. There will be live performances, food trucks, and lots of holiday cheer—all for free.

7. The Dickens Fair

Until December 22nd | $45

Photo credit: Dickens Fair

Travel back in time at the Dickens Fair, held at the Cow Palace. This immersive holiday experience recreates Victorian London with winding streets, pubs, shops, and live performances. Explore with your partner, sip on mulled wine, and enjoy themed events like a pub crawl with Jekyll & Hyde or a chocolate and champagne tasting.

Whether you’re dancing, shopping, or just soaking in the festive atmosphere, the Dickens Fair is a unique holiday outing.

8. Winter Walk in Union Square

December 13th-22nd | FREE

Photo credit: Winter Walk

From December 13–22, Winter Walk transforms Union Square into a festive holiday hub. Walk along Stockton Street, which will be decked out with lights, snow machines, live performances, and plenty of seasonal food and drinks.

Don’t miss the special croissant creation—the Winter Walk Matterhorn, filled with tiramisu Chantilly cream. Snap some photos with Santa, watch carolers, and enjoy the lively holiday atmosphere.