Our Annual Tradition: Celebrating Christmas in Downtown San Francisco

There’s something about Christmas in San Francisco that never gets old. The lights, the music, the energy of people gathering together — it’s a feeling we look forward to every year. Over time, our Downtown holiday outing has become a tradition we cherish, a way to slow down, soak in the season, and make memories in the heart of the city we love.

We kicked off the day with Winter Walk, hosted by JPMorgan, which set the tone perfectly. Downtown felt alive and festive. A bar truck served up warm holiday drinks, an Old Navy pop-up brought some playful retail cheer, and a group of Christmas carolers filled the street with classic songs that instantly put everyone in the holiday spirit. One of the highlights was a fun Super Mario Brothers photo opportunity, complete with Mario and Princess Peach — a playful surprise that drew smiles from kids and adults alike. Of course, no holiday walk would be complete without photos with Santa, a moment that always feels nostalgic no matter how old you are.

From there, we made our way to Union Square to see the iconic Christmas tree. Standing there, surrounded by lights and people pausing to take it all in, reminded us why this spot remains such a classic centerpiece of the season. It’s one of those moments where the city feels especially magical.

Next, we stopped by one of our favorite holiday sights every year — the Westin St. Francis. Their Christmas decorations never disappoint. The warmth, elegance, and attention to detail make it feel like stepping into a classic holiday film. It’s easily one of our most-loved decorated hotels in the city, and we never skip it.

Lunch was at the Neiman Marcus Rotunda, a tradition within the tradition. We lingered over a meal beneath the iconic dome — I ordered the burger, while my wife enjoyed the lobster sandwich. It’s one of those places where time slows down just enough to savor both the food and the atmosphere.

After lunch, we stopped by Williams Sonoma, which felt especially meaningful this year, as it may be their last season in that location. Walking through the store brought back memories of past holidays and the role these familiar spaces play in shaping our traditions.

We ended the day at Ghirardelli Square, where the holiday decorations, live music, and gathering crowds created a beautiful finale. A violinist and pianist played modern music, drawing people together as they stopped to listen, record videos, or simply stand still for a moment. It was one of those scenes that perfectly captures the spirit of the season — strangers sharing a quiet, joyful experience together.

This annual Downtown Christmas tradition has become more than just a day out. It’s a reminder of how special it is to experience the city during the holidays, to revisit favorite places, and to create new memories year after year. San Francisco does Christmas in its own unique way, and we’re grateful to be part of it — every single season.