My husband and I love to visit big cities during the holidays. Because we live in a small town, we enjoy traveling to a large metropolitan area in December with a walkable downtown before Christmas or the week between Christmas and New Year’s Day. In big cities, we can find holiday markets, beautifully decorated shops and streets, special Christmas events/shows, and holiday displays. We love the hustle and bustle of everything, the excitement in the air, and how festive it all is.
It isn’t that our small town doesn’t offer anything Christmasy, it’s just that holidays seem to be the best time to visit the big cities. Many provide unique experiences and attractions we can’t get at home.



Over the years, we’ve traveled in December to Paris, Hamburg, Dallas, New York City, Chicago, Washington DC, Hong Kong, Lake Tahoe, Los Angeles, Pasadena, San Diego, and San Francisco. Because San Francisco is within driving distance from our home, we returned to enjoy some pre-holiday festivities and celebrate my husband’s December birthday. We had a fantastic time!
I’m sharing our five-night itinerary here and including links to places we went in case a trip to San Francisco is in your future. Even if not, I hope you find these snapshots from San Francisco interesting.🙂
San Francisco Itinerary
Day 1:
We arrived in San Francisco on a rainy Saturday around 2:00 p.m. and checked into our beautiful hotel for the night. The Christmas decorations were abundant, and the atmosphere was very festive. We were upgraded to a suite (!!!), and there was a sweet surprise in our room—a birthday cake for Tony and a bottle of champagne.
We decided to stay in and dine at the hotel restaurant for dinner. We had a lovely table by the window and enjoyed a delicious, unhurried meal.
Day 2:
We began our day with breakfast at the hotel and then a walk to Chinatown. Afterward, we returned to our suite to read and relax before our check-out at 2:30.
We left the Ritz Carlton and checked into our next place, a one-bedroom apartment, for the remaining four nights. We had afternoon reservations for Tea at the St. Regis, but it turned out to be disastrous. It’s a long story but with a good ending. ☺️ We gave up on the tea experience, and the manager made it right, so we had a wonderful early dinner instead.





Day 3:
We slept in and awoke to another rainy day. Tony and I both had some work to do that morning, so we stayed in the apartment and then took an Uber to Chez Maman for lunch. We savored our long lunch with a glass of wine, and between the food, the waiters speaking French, and the tight tables, we felt like we were in Paris. 🥰 From there, we spent a leisurely afternoon shopping in Union Square and admiring the gigantic Christmas tree in the center, and then walked back to our apartment to relax.
We had late dinner reservations at the legendary Tadich Grill, a quick walk from our accommodations. Our seafood meals were fabulous! We’d been once before and were glad we returned. From there, we walked to our last stop of the day, The Dawn Club. We had gone there when we were in San Francisco early last year and knew we wanted to return. We made reservations, which ensured a lovely table, and had such a fun night enjoying the live jazz and unique cocktails. I highly recommend a stop here if you like jazz.




Day 4:
Tony and I walked to The Grove for a yummy brunch, then from there, walked down to the Ferry Building to shop and pick up a few things at Mariposa Baking Company. They carry a vast selection of gluten-free baked goods, so we typically stop there when in San Francisco. We wandered around briefly, then hopped on a cable car and rode it to Nob Hill. From there, we walked to The Fairmont Hotel to admire the enormous, gorgeous Christmas tree and stroll through the life-sized gingerbread house. The hotel is always beautifully decorated for Christmas, and if you enjoy afternoon tea (and don’t need it to be gluten-free,) I highly recommend making a reservation there.
Next, we walked over to the stunning Grace Cathedral for a self-guided tour. The cathedral’s stained glass and works of art are worth seeing. They rival the cathedrals we’ve visited in Europe. From there, we walked down to the Mark Hopkins Hotel for a sunset cocktail at the Top of the Mark Sky Lounge. The weather was sunny and clear that day, so the views of the sunset and the Golden Gate Bridge were spectacular. Following our holiday drinks, we hopped on another cable car and rode to Union Square. We window-shopped for a while before heading back to the apartment.
We relaxed and then changed for dinner at another French restaurant, La Société Bar & Café. Tony and I both ordered the steak frites, which were so delicious! They brought Tony an ice cream sundae for his birthday, and we shared an excellent Bourbon au Chocolat. Coincidentally, the La Sociéteé mixologist Engracio Clemena also created the cocktail menu at The Dawn Club! He stopped by our table, and we had fun chatting about his passion for his craft. Our last stop for the day was at Local Edition, an underground club where a jazz orchestra performs weekly. The music was awesome! What a fun night we had!












Day 5:
It was another slow morning, enjoying coffee and reading. I had a Zoom meeting, so we didn’t leave the apartment until nearly lunchtime. We meandered down the street to grab a quick, light lunch, then walked along Market Street for more Christmas shopping. We stopped in a few places along the way and ended up at the San Francisco Centre. From there, we took a cable car to Ghirardelli Square and wandered around. We dined at John’s Grill for an early meal and returned to the apartment to get dressed up for the highlight of our trip: Holidays with Boyz II Men and the San Francisco Symphony. Wow! What a magical night! It was even better than we expected! The gorgeous venue was the perfect place to listen to this performance.






Day 6:
After a light breakfast at our apartment, we packed up, checked out, and sadly, said goodbye to San Francisco.
“You wouldn't think such a place as San Francisco could exist. The wonderful sunlight there, the hills, the great bridges, the Pacific at your shoes. Beautiful Chinatown. Every race in the world. The sardine fleets sailing out. The little cable-cars whizzing down The City hills. And all the people are open and friendly.” Dylan Thomas
P.S.
Because Tony and I have been to San Francisco many times, we decided this trip would be less about sightseeing and more about doing whatever we felt like. We made dinner reservations, so our evenings were planned, but we left a loose schedule for the daytime. We’ve previously visited many of the hot spots in the city (museums, parks, neighborhoods, Fisherman’s Wharf, etc.), so if you have any questions, ask away!
Thanks for reading! If you enjoyed this post, please hit the “like” button! I appreciate it!
With love, Natalie xx
Have you ever been to San Francisco? If so, what are your favorite places there?
Helpful Links
17 Free Things To Do in San Francisco
Gluten-Free Friendly Restaurants in San Francisco
San Francisco Itinerary: 2, 3, and 4 Days
Best Bars & Restaurants with Live Jazz in San Francisco
The 24 Best Things To Do in San Francisco
Incredible photos, and such wonderful festive memories you made there ✨🎄 – and you’ve made SF a definite city for a 🇺🇸 wish list! 😍 (I’ve never been further up the coast than LA). And how wonderful that you got to Grace Cathedral, too. ❤️
This is so wonderful. I grew up there and this hits as exactly how I as a former local would love to spend a week. Beautiful pictures. ❤️❤️