The Best 4-Day Itinerary in San Francisco

Anytime, we have an opportunity to go see a favorite band in another city we book the ticket. It's even better when the band is THE GROWLERS! (I mean... Brooks Nielsen). Our trip to San Francisco started off with a concert and turned into a great long weekend with some of our California friends. Keep reading to see a day by day itinerary of our favorite highlights of San Francisco!

Day 1: Union Square, Chinatown, Golden Gate Bridge

We landed late on a Thursday evening around midnight, and got to our hotel around 12:30 am, so the real fun started the following morning.

We started our day with the best breakfast burritos at Taqueria Cazadores, then made our way to Union Square for a free walking tour . The tour takes about 2 and a half hours and covers most of downtown San Fran: Union Square, Chinatown, Financial District, and Embarcadero. We had the greatest guide named, Dany and you could tell his passion for his city. He had the greatest stories about the people, places, historic events and current affairs of the city. Some of my favorite highlights were the buried ships under the buildings, the influential women, the gold-diggers and gold rush, and effects of the earthquakes.

Walking tours are one of my favorite ways to get to know a city. The tours give you a good layout of neighborhoods that you'll be traveling through during your time there. If you've never been on one I HIGHLY recommend giving it a try.

During our trip, it was Lunar New Year. So a highlight to this walking tour was going through Chinatown. We learned more about the significance of the celebration, as well as the importance that Chinatown plays in the culture of San Fran's success. We made some great stops, like a fortune cookie factory, the alleyway with the original layout of Chinatown, the home of Bruce Lee and our guide did a great job of pointing out lots of dim sum restaurants for us to try at a later time.

Our tour ended at the Ferry Building, which is where my friend Michelle joined us for the rest of our trip!

In the Ferry Building we grabbed lunch and enjoyed the views of the Bay Bridge and then grabbed a scoop of ice cream from Humphry Slocombe. You have to try a scoop of the "surprise breakfast." You won't be disappointed!

Next, we hopped in an Uber and did a quick trip over to the Golden Gate Bridge. Since the weather was nice, we walked the entire distance to and from with beautiful views of the bay, Alcatraz, and tons of dolphins. The entire bridge is 1.7 miles each way. With all the stops to take in the views and pictures it took us about an hour and a half.

We wrapped up that evening grabbing dinner at Suppenkuche with another dear friend from college, Lizzie. We loved having the chance to catch up and meet her sweet baby girl and husband. Lizzie has lived in San Francisco for the past six years and gave the GREATEST recommendations for the remainder of our trip. We ended the evening with a nightcap at Brass Tacks.

Day 2: Alcatraz Island

This day we started with breakfast with our friend Lizzie, at Kantine. They had great coffee and sandwiches.

We couldn't stay too long since we had to make our way down to the ferry port to hop on the ferry to Alcatraz Island. We took the guided audio walking tour which was super informative and extremely sad. We also learned a lot about Native American presence on Alcatraz Island back in the 70's which really opened my eyes to the history of San Francisco at the time. The day was a bit rainy and drizzly, but perfect since we spent a few hours here inside.

After Alcatraz, we walked about 15 minutes to Pier 39 to catch a glimpse of the sea lions.

Then we hopped on a bus and made our way back to Chinatown. After a chilly rainy afternoon, we each decided on a big bowl of noodles at Chong Qing Xiao Mian to celebrate New Years and to ensure Michelle had a chance to see Chinatown. We loved getting to share a lot of interesting facts with her from our tour the previous day.

After dinner, we grabbed a few drinks to prep for our concert and to stay out of the rain. Our concert was later that night at August Hall. August Hall was absolutely beautiful, I loved that even though it was a sold out show they didn't pack the place. Once the show was over, we made our way back to our side of town and ended our night at a martini bar called Martuni's.

Day 3: Wine Country

Day three we rented a car from the airport and made our way out to wine country. Our friend Lizzie recommended some AMAZING wineries in Healdsburg. The drive there was stunning. We were shocked how nervous everyone was about the rain that was projected to come that day, and our friend kept telling us that people in Californians are not prepared for rain due to the poor infrastructure on the roads. (She was not wrong...). On the bright side, this made for easy entrance to all the wineries we wanted to see!

Our first winery of the day was called Cast. It was absolutely lovely! The wine was to die for. The staff was super kind and friendly and it turned out one of them used to live in Chicago next to the building that I work. (What a small world!) After our tasting, we unanimously voted that the Zinfandel was our favorite.

Our second winery for the day was called Comstock. Again due to the poor weather forecast, these wineries were not nearly as crowded as we would've expected for a Sunday on a holiday weekend. So we got to enjoy the wineries in peace which let us ask all kinds of questions and enriched our experience. We also tried their charcuterie board and had to request a special order of the edamame hummus and crackers (it was to DIE for!)

After our second tasting, we decided that we needed to grab a snack, so we grabbed sandwiches in the pouring rain at the Dry Creek General Store.

Once we were done, we decided we wanted to stop in downtown Healdsburg. We did one more full tasting at Williamson Wines, they had a lovely cheese pairing with each wine (our favorite was the lasagna cheese). Then we stopped at Marine Layer winery for one last glass before dinner in Healdsburg. For dinner we stopped at PizZando. We ordered the crispy artichokes, the rosemary focaccia, bucatini amatriciana and the Spicy Coppa pizza.

Then we made our way back to the city. Before turning in for the night, we decided on one last nightcap across the street at Martuni's. It turned out to be karaoke night and it must've been invitation only because every performer seemed to have been in musical theater or on Broadway! Everybody who performed with the live piano player was absolutely PHENOMENAL so we felt like we hit gold on the entertainment.

Day 4: Golden Gate Park, Castro and Mission's District

After running up and down the hills of San Francisco, we were starting to lose some steam, but knew that we had until 4 o'clock to see our last few destinations before having to get back to the airport. So we decided to make the most of it. We stopped for a quick breakfast at Café Reveille. We walked around for a while over there before moving on to see the Painted Ladies.

Then we spent most of the afternoon walking around Golden Gate Park. With the weather being as unpredictable as it was, we spent some time in the Conservatory of Flowers during a torrential downpour. We walked around multiple nooks and crannies in the park and got the chance to enjoy the outdoors before spending multiple hours on an airplane. My favorite space was the National AIDS Memorial Grove. The trees were so beautiful and the memorial was so peaceful.

The last thing that we did before heading back to the airport was make one last stop in Castro to grab lunch at Souvla and then a scoop of ice cream at Bi-Rite creamery.

All in all, San Francisco despite the unpredictable weather, was an absolute delight! The friends, architecture, history, and music made this long weekend one we won't forget! We look forward to having any opportunity to go back and visit.