Things You Must Do This Holiday in San Francisco

Every December, I find myself looking for those little traditions that make the city feel alive. San Francisco has a way of turning familiar places into something magical — hotels become gingerbread wonderlands, rooftops turn into holiday markets, and Union Square feels like the center of the season. If you’re planning a holiday outing, here’s how I’d spend the day.

Fairmont San Francisco

The Fairmont is always the first stop. You walk in, and there’s this massive two‑story gingerbread house that smells as good as it looks. It’s the kind of display that makes you feel like a kid again. And if you’re around December 19–21, the rooftop garden hosts a holiday market with local makers — browsing stalls while looking out over Nob Hill is a holiday mood all on its own.

InterContinental Mark Hopkins

Right across the street, the InterContinental leans into the season with cozy décor and plenty of photo ops. Santa usually makes an appearance, which makes it a fun stop whether you’ve got kids with you or just want that classic holiday snapshot. It’s quick, cheerful, and worth the detour.

Westin St. Francis

The Westin’s Castle is one of those traditions that never gets old. It’s whimsical, detailed, and completely over‑the‑top in the best way. Grab a hot drink in the lobby and take a few minutes to admire it — it’s the kind of pause that makes the holiday rush feel slower, sweeter.

Photo credit: crawlsf.com

Union Square

Union Square is the city’s holiday heartbeat. The tree towers over the plaza, carolers drop in with music, and craft stations pop up on weekends. At night, skating under the lights while the city buzzes around you is one of those only‑in‑SF experiences. It’s busy, it’s joyful, and it’s everything the holidays should feel like.

The Vault Garden

End the night at The Vault Garden. They turn their outdoor space into a winter wonderland, with festive cocktails, big shareable plates, and live music. Heated seating makes it cozy even when the air gets chilly. It’s the perfect spot to linger, laugh, and wrap up the day.

That’s my version of a holiday day in San Francisco — a mix of tradition, community, and celebration. Whether you’re skating, sipping, or just wandering through the lights, these stops guarantee a season full of memories. And honestly, that’s what makes the holidays here so special: the city feels like it’s inviting you in.