My bestie and I live several states away so we covet the only four or so days we get to be together each year. We move our daily, onscreen Marco Polo conversations to face-to-face, real life while exploring a different city and it is LIFE GIVING. We both agree that after about a decade of doing this, our 2025 trip to San Francisco might've been our best trip yet. Below I'm detailing what we did, where we went, what we ate and some other great suggestions and resources to help you plan your San Francisco girls trip!
We chose January solely because it seems to be the most quiet month from ongoing kid activities. The weather ended up being nearly perfect for our entire trip. Upper 50s and sunny! We also went during the workweek (Sunday-Thursday). Not only does that make it easier on the dads juggling work and kids, but things aren't as busy and aren't quite as expensive from a traveling standpoint.
Where We Stayed
Hotel Zeppelin San Francisco in Union Square neighborhood
Let's start with where we stayed. We were back and forth about location and hotel options and ultimately decided to stay in the Union Square neighborhood at Hotel Zeppelin and were glad we did. To be honest, we were a little worried we weren't hip enough. Their tagline is "bold, bohemian and anything but basic". It also says it's a place for the rebels! I definitely don't consider us "rebels" but let me be clear, not only did we feel 100% comfortable at this hotel, it also brought us out of our regular mom lives a little bit more. We weren't in a regular room at the Hilton, we were at this boutique hotel that had a cool, relaxed vibe, which is just what we were after.
Here's what we loved about it.
It was a great central location to all of the things we wanted to see and do and an ideal jumping off spot. It also wasn't super touristy like some of the other spots we were eyeing. I felt like it gave us a good glimpse into downtown San Francisco life. The hotel itself was a small boutique hotel- funky and charming and felt safe. It is near the Tenderloin District which can be a bit more dicey, but it is across the street from the JW Marriott and literally only two blocks from Tiffany & Co. so you know- it's in the city. We kept our strolling to the Union Square side, as we had been advised, and never had any trouble and loved exploring and shopping in that neighborhood.
Check out Babble's IG for video highlights of the property here.
DAY 1:
Our only real plan for Day 1 was a great dinner reservation and exploring our neighborhood. After an Uber from the airport and checking into our hotel, we went in desperate search for a long, overdue lunch. We were immediately beckoned from across the street and drawn into Johnny Foley's Irish House where we kicked off the trip with some fish & chips and a pint and a half of Harp. Girls weekend had officially started.
Afterwards we strolled along Union Square and stopped in some shops. Hello Sephora! It's so much more fun to shop for makeup with a girlfriend. The afternoon went quickly and after freshening up at the hotel we Ubered to Pier 39 for our only reservation of the trip.
Pier 39 was adorable, especially lit up at dusk with the sun setting over the bay. So many cute families taking in the magic show on the boardwalk or finding goodies in the souvenir shops. We strolled there until our reservation at Fog House Fish House. The view was picture perfect with the sun setting just behind the Golden Gate Bridge as we looked out on the water and boats. It was definitely worth making a reservation requesting a table with a view! We chose this restaurant specifically for their view and for a bowl of their famous clam chowder, but our favorite dish ended up being the ahi poke (and truth be told, the bottle of NZ Marborough Sauvingnon Blanc). I felt like we were already easily checking a lot of the San Francisco boxes- Golden Gate Bridge ✓, Pier 39 ✓, fresh seafood ✓...bring it on!
And then, as all 45 year olds do, we grabbed a 24 pack of water at a CVS and headed back to our hotel by 9pm.
Day 2:
We stayed in bed chatting until noon. It was glorious. No need to be anywhere and zero distractions from a great conversation with my girlfriend on a Monday morning.
We finally moved the conversation to the totally hip and inviting lobby and started the day with coffee at Cafe Zeppelin at the hotel. We enjoyed delicious coffees and pastries cozied up next to their fireplace. Absolutely lovely!
From there we took the cable car from Union Square to Lombard Street. Honestly the cable car might be touristy but it was one of the highlights of our trip! So unique and fun and oh so San Francisco! The Union Square cable car station was very busy and popular, but also completely easy to navigate without any prior planning. I've heard you can go one stop away and get on without waiting, but as tourists do, we stayed in the short line and watched how they turn the cable car and took in the full process of it all. We immediately wished we got the full day pass because it was not only fun, but really easy to hop and off and get to see a lot of the city that way.
We had planned on riding the cable car all the way to Fisherman's Warf, but hopped off on Lombard Street. We took photos at the top of the crooked street and walked down it talking about what it must be like to live right on that famous street and then it was an easy walk from that area over to the Fisherman's Warf.
We strolled up and down the Warf again peeking in souvenir shops and taking in the view and then stopped for lunch at Flying Ninja because we heard that San Francisco has incredible sushi! We were not steered wrong.
From there we took the short walk to Ghirardelli Square, (you know their chocolate and if you haven't yet, please try their brownie mix you can get in the grocery store. Our family's fav!) We shopped at the boutiques (going back to one in particular a whopping 3x because we kept deciding we needed more of their treasures), got chocolate souvenirs for our family and skipped the chocolate experience ourselves (even though it was enticing) and hit up a charming wine happy hour while we mapped out our next steps. We had planned to walk over the Golden Gate Bridge, but it was getting chilly and windy so we decided to skip it. (I do want to link An Insider's Guide to Walking Over the Golden Gate Bridge in case you are interested. We'll have to hit that up the next time we're in SF.) Instead we took the cable car from Fisherman's Warf back to Union Square.
We did a little shopping and daydreaming at Tiffany & Co. and hit up Zara and then shared a pasta dish and a couple of glasses of Pinot Nior and great conversation at Cesario's. It was the perfect end to a laidback and delightful day together in San Francisco. Once again we were back at the hotel early-ish where we watched the Bachelor premiere and prepped for our big day...
DAY 3:
This the kind of day dreams are made of. A bucket list item that couldn't be more perfect for a girls weekend. We were headed on the Napa Valley Wine Train! The shining star of our trip.
When we started researching where we wanted to go for our girls weekend and started to settle on the San Francisco area in California we found out about the Napa Valley Wine Train and we knew we wanted to make this happen.
I cannot describe to you how incredible this experience was. It was a pinch me type of day with my best friend that we will talk about and dream about forever. We knew it was special from the minute we were greeted like VIPs with a glass of crisp sparkling wine and crooners as we boarded the vintage train.
The Napa Valley Wine Train has a few different trips so check their website, but we did The Legacy Experience 6 hour tour which included a 4 course meal and multiple wine tastings. The first of which took place in the open-air Pullman rail car overlooking the famed Napa Valley welcome sign.
Throughout our excursion we enjoyed two seated tastings at both Charles Krug, Napa Valley's oldest winery estate, and V. Sattui vineyards, which makes you feel like your in Italy!
The gourmet 4 course meal served aboard the train was out of this world. In fact, by far the best food we had on our entire trip (and we enjoyed some great food). We savored every bite and every sip on this gorgeous and unique train while vineyard views went by outside our window. A delicious whipped brie with honey and crostini would be placed in front of us at precisely the right moment. Just when you didn't know you needed a little bite until it was there and then realized it was just what you needed in between wine tastings.
I love that we got to choose our main course (which both of us ended up going with the Truffle Mushroom Risotto) although our favorite dish was the Smoked Salmon Benedict we savored just after the train embarked on its first leg of the trip. Not to mention the dessert that capped off our experience on our final leg. I enjoyed the vanilla Crème Brulée while Anissa had the Chocolate Lava Cake (I guess we dug in too quickly because we didn't even manage a photo!;)).
To top it all off, our tour ended with an optional dance party in the open air train car (think Dirty Dancing soundtrack and other old time favorites). We laughed and spun around with all our new friends on the train! This joint experience brought out the fun, carefree side of every one of the passengers. Exactly what any good vacation and special occasion should do!
I truly can't say enough about it. Perfectly paired gourmet cuisine, award winning wines, vineyard views and incredible hospitality, all flawlessly executed by their team from food and beverage to hospitality and entertainment. They have found the magic at Napa Valley Wine Train and created an enchanting experience for all of us to enjoy.
I do want to point out that getting to/from Napa and San Francisco was not as easy as we had hoped. Yes there are some shuttles, but they primarily leave from the airport, so for us it didn't make sense to backtrack to the airport from Union Square just to hop on the shuttle (when we looked the shuttle was $60 each way) and it would've meant an even early wakeup call. We wanted to be in Napa by 9:30am and it was a little over an hour to get there from our location. We researched several private car services but they were expensive ($300 or more each direction) and we also looked into taking the ferry and were told about the bus. At the end of the day, we ended up just scheduling an Uber which worked out just fine. It was around $120 each way, but made it easy picking us up at our hotel and dropping us directly at the station. Just know if you are staying in San Francisco and wanting to head to Napa and the Napa Valley Wine Train to factor that into your planning for budget and time. TOTALLY worth it BTW if that hasn't been clear. I would 100% recommend this experience. Top 10 day for sure.
When we got back to San Francisco we settled in for dinner at PSL on Post, the restaurant conveniently connected to the Hotel Zeppelin, where we soaked up our fun with a delicious smash burger and fries. We were thankful for the accommodation of having a great restaurant onsite at the hotel! A great end to bookend an incredible day.
DAY 4:
We had planned for feeling a little rough on Day 4 and you know what...we weren't that bad. At 45 we know staying hydrated and eating are key and we took some extra precautions before, during and after our wine train experience. (Jury is still out on if we think the Recovery Patch did anything, but it was worth a shot. Of course Liquid IV is nonnegotiable for any girls trip at this point.)
We also had already spied a good looking greasy spoon that seemed popular with the locals and it was just what the doctor ordered. We hit up Pinecrest Diner and these midwest girls did not f@#$ around ordering up some chicken fried steak and eggs and of course coffee. This breakfast was so good I would've been hard pressed not to go there again if we had another day. Still thinking about it.
It was over breakfast that we decided we were going to try Waymo for our next transportation option. If you aren't yet familiar, it is a driverless, self-driving ride-share and they were all over San Francisco. We expected to be totally freaked out riding in it and we're blown away by how comfortable we felt, and actually how we preferred it to Uber and Lyft. The car was so nice and so clean and we didn't have to worry if the driver was creepy or too chatty or smelled odd. We were also in full control of the temperature and music. We felt completely safe and would 100% take Waymo again. Also, it was priced very similar to Uber and Lyft so it made it a great option. See our full experience here. We took Waymo over to the Painted Ladies. They are so adorable and even better, they are the standout, front and center, in photos with a picturesque San Francisco city and bay backdrop. This whole area was so cute- the park, the houses, the view!
We were disappointed to learn that the Full House house from the opening credits of the show is not actually one of the Painted Ladies. It is located about a mile north of Alamo Square Park where the Painted Ladies are. If you are interested and want to take a deep dive into the Full House house (and who can blame you), check out this article from Architectural Digest. In my mind though, I'm choosing to think that we saw it. Close enough.
We went on a bit of a longer walk through cute neighborhoods to get from the Painted Ladies to the Haight-Ashbury neighborhood. Known for it's 60s vibe and vintage shops, we took it all in including going home with a few vintage scarf treasures.
It was at the end of the street where we stopped at Cha Cha Cha's Caribbean Tapas & Bar for a half pitcher of the sangria they are known for and really great chips and guac as well as shishito peppers. Again, tough to beat great food, drink and conversation with one of your oldest friends.
Replenished we decided to go just a few more blocks into Golden Gate Park. It was WAY bigger and WAY more beautiful than I imagined! We weaved through taking in all the activities and cute dogs along the way when we decided we were winding down.
Without a real plan we walked over to the Inner Sunset neighborhood on 9th & Irving (or as we were told, it is called "Nerving" by the locals). Another adorable neighborhood with little boutiques and lots of good looking restaurants with a great variety of cuisine to choose from. We decided to go with a spot that had a little line outside before it opened, Fiorella Neighborhood Italian. It was Wednesday night at 5pm and the only spot to sit without a reservation was at the bar so you know it's good! We hit up a happy hour beer and shared a burrata pizza. A great meal to close out our vacation.
Waymo was little more expensive than Uber and Lyft for the way back to the hotel so we opted for old school Uber and got back to our hotel to pack up for our ridiculously early alarms to go off for flights home.
We're still talking about how this trip was a perfect mix of easy and laidback San Francisco exploring, great food, incredible Napa bucket list indulging and getting reconnected with and old friend while getting acquainted with a charming city.
Check out the video highlight reel on Babble's IG here. Also, while you are there be sure to follow @babblewithbrookeig for the anti-influencer take on everything for 40+ ladies- fashion, food, beauty, travel, parenting, wellness, entertainment and more. The best way to not miss a thing is by signing up for the Babble newsletter on this site. Take what you want and leave the rest. ;)
Of course there were more things we could've seen and done, but we will leave that for the next trip. If you are still looking for more ideas, check out what my friend The Traveling Spud has to say here. She used to live in San Francisco and was a great resource for me.
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