Have you ever booked a trip that was so last minute that you had to scramble to find a cheap flight, decent accommodations, and plan for activities all at once? Our trip to San Francisco and Napa Valley was that kind of trip. It started when Shreya and I were having coffee at our new favorite coffee spot in Houston when we were trying to book a last-minute vacation somewhere and saw cheap flights to San Francisco. At first, we weren’t too thrilled with the idea of visiting San Francisco again because we had gone before, but we ultimately decided that it had been too long since our last visit and that this time around we would spend more time in the city. Plus, we knew from a prior trip that we could hop over to Napa Valley in an hour so of course the prospect of having a day of wine drinking sealed the deal. After a late-night of trying to coordinate flights and book hotels at once, we were on our way to the Bay City. If you’re interested in finding out how we spent 5 days (3 days in San Francisco, 2 days in Napa Valley) keep on reading!
Day 1: Travel to San Francisco, Union Square/Downtown
We started our day bright and early Friday morning with a 5 a.m. flight to San Francisco with a quick layover in Dallas. We landed in San Francisco around 8:30 a.m. and quickly took an Uber to our hotel downtown. We stayed at the Hilton Union Square because of its prime location and because we had good experiences with prior stays. The hotel didn’t have a room ready for us so we dropped our bags off at the bell stand and decided to venture out for breakfast. At this point we were starving and in dire need of caffeine so we opened up Yelp and found a highly rated crepery near the hotel – hurray!
We made our way over to Honey Honey Cafe & Crepery and had a delicious breakfast of fluffy waffles, pancakes, roasted potatoes, eggs, and chicken sausage. And of course, lots and lots of coffee!
After being happily fed and caffeinated, we realized we still had hours until we could check into our room. We decided to walk around downtown, which first included a stroll through the shops and malls in Union Square. We ooh and ahh’d at the designer shops, the cute trolleys, and mentally tried to remember where we wanted to return once we were showered and freshened up.
Next, we ended up walking through Chinatown by accident (we wanted to save it for another day when we could return for photos and lunch) and continued our aimless walking until we somehow reached the Ferry Building Marketplace where we were greeted with blue skies, palm trees, and a rush of people heading towards to the building for lunch. The Ferry Building reminded us of an indoor farmer’s market with local coffee, wines, cheeses, and a variety of other things to try and buy. We explored the building a bit and then went outside to sit by the water when, luckily, the hotel texted us that our room was ready – yay! At this point we were so exhausted from the early travel day that we immediately threw ourselves in bed and tried to relax before getting ready for the night.
Next, we got ready for the night and made our way to the View Lounge, an iconic rooftop bar with stunning views of the city. Since we went to that bar a few years ago, we knew it would be very popular around sunset so we tried to get there an hour beforehand to stake out a prime spot. Unfortunately the tables by the window were all taken, but we managed to get a decent table.
We left the lounge when it started getting busy and went to Fino Ristorante & Bar to make our 6:30 p.m. dinner reservation. At this point we were so exhausted that we ended our night by enjoying a hearty plate of pasta and returned back to our hotel in a happy food coma.
Day 2: Golden Gate Bridge, Fisherman’s Wharf, Pier 39, and Twin Peaks
Since we love brunch so much (and because our college friends happened to be in town for the weekend) we met up with them at the Rambler for an awesome brunch with mimosas. We had the Rambler (breakfast combo with an omelette and potatoes) and huevos rancheros (sans hueveos because Tina does not like eggs). It was exactly what we needed before our busy day of touristy activities ahead!
No trip to San Francisco is complete without visiting the Golden Gate Bridge. Of course you can see this stunning structure from a distance, but why not actually walk the 2 miles across the bridge? We had no idea it was that long when we first started our walk, but we eventually tracked our steps when we realized we had been walking for a really long time. We ended up at the Golden Gate visitor center where we followed the crowds to the bridge’s walking lanes. From there we enjoyed amazing views of the city, saw a few dolphins in the bay, and made our way to the Vista Point scenic view point where we took photos.
We thought the walk across the Golden Gate Bridge counted as exercise which means our next stop, Ghiradelli Square, was well-deserved! We took an Uber from the bridge to Fisherman’s Wharf where we enjoyed sinfully delicious (and famous, apparently) ice cream sundaes made with Ghiradelli chocolate.
As our super friendly but brutally honest Uber drive told us, Fisherman’s Wharf and Pier 39 are total tourist traps but still a must-see at least once. Since we were still full from lunch and our sugar coma, we just walked around the shops, strolled around the pier, and watched the sea lions wrestle each other for a bit. Honestly, there’s not much else to do here unless you want to hang out by the nearby beach park or shop around.
Since the day was rapidly coming to an end, we decided we wanted to catch the sunset at a scenic location. Based on other suggestions and blog posts, we chose Twin Peaks which has one of the best views of the cities! There’s a slight hike to the top, but there are stairs, so no worries there. We would recommend you wear some flat shoes for this as it’s not completely smooth once you are at the top. The peak quickly filled up with other people looking to take photos, but we got there just before the crowds arrived.
Since our trip was last-minute and we didn’t have much time to prepare, we had the hardest time finding dinner availability at the famous, top-rated restaurants in the city. We managed to make a late reservation at Limon Rotisserie, a trendy restaurant serving modern Peruvian cuisine which turned out to be absolutely amazing. Seriously, we had the best ceviche ever!
After dinner we decided that this would be our main night of bar hopping. Boy, were we wrong. First, we had a hard time finding where the main bar districts were, but eventually figured out we should head to the Mission District for most of our drinking. We found some amazing bars, but to be honest we were distracted by the fact that we were overly dressed compared to the local patrons. Just to give you an example, we were wearing traditional “going out” dresses, mini skirts, stilettos, etc. whereas we saw many local women dressed casually in cutoff jean shorts, jeans, t-shirts, and sneakers. Since our prior trips to San Francisco were very brief and we didn’t explore the nightlife, we had no idea how to dress for the bar scene – oops!!
Day 3: Chinatown, Alcatraz, Lombard St., Painted Ladies
We ended our night pretty late so we slept in a bit and started our day around 10 a.m. in SF Chinatown -the oldest and most established in the US, and the largest outside Asia. As we walked through Dragon Gate, which is one of the main entrances to Chinatown, we were greeted by souvenir shops selling a variety of trinkets, red lanterns decorating the streets, and delicious smells from the local restaurants.
We had skipped out on breakfast, so by the time it was 11 a.m., we were starving from all of the walking. One of our followers from Instagram who is local to SF recommended we check out Z & Y Restaurant, so we made our way to this well known restaurant that has served famous guests from Presidents to Vice Presidents. We ordered Chicken With Explosive Chili Pepper, Crispy Garlic Flavor Prawns, and Chicken Fried Rice. Everything was delicious and authentic – we definitely walked out with a food coma!
To burn off some of the calories we just ate (and to wake ourselves up from the food coma), we decided to walk from the restaurant to Pier 33, where we boarded on the Alcatraz Cruise for the tour of the infamous maximum high-security federal prison, which housed inmates like Al Capone and Machine Gun Kelly. A quick tip – make sure you book tickets ahead of time on their website since they sell out pretty fast.
You can do the tour on your own, but we wanted to learn the detailed history of the prison, so we opted to do the 45 min audio tour. The audio presented was very well done and it guided us through the prison cells, dining hall, library, prison yard, warden’s office, as well as explained the escape attempts by prisoners. We really enjoyed this tour and highly recommend it!
It was around 2 p.m. when we disembarked from the cruise and we were in desperate need of some caffeine. We stopped by Biscoff Coffee Corner and grabbed lattes (and free cookies!) as we made our way to Lombard Street, known as the “crookedest” street in the world. We spent some time here watching people attempt to drive down this street – one car totally messed up their tires as they hit the curb during a turn, ouch!
If you grew up watching Full House like we did, then you know why we had to come visit the Painted Ladies! Even though the real Full House house isn’t one of them, you will still notice that the opening sequence of each episode ended with the family picnicking in Alamo Square Park with the picture-perfect row of Painted Ladies in the background. The view from the park was gorgeous, especially during sunset. It’s also a perfect spot to have a picnic if you have an afternoon to relax.
After visiting the Painted Ladies, we headed to pick up our car rental for the next day’s drive to Napa. When we returned to the hotel we got ready to enjoy our last night in San Francisco. Naturally being a Texan, we crave tacos and margaritas all the time – and this night was no exception for dinner. A simple yelp search pointed us towards Tacolicious in Mission District, and it definitely didn’t disappoint. Both the drinks and the food were exceptional and we loved the ambience of this restaurant.
No dinner is complete without dessert, especially ice cream! Since Bi-Rite Creamery was walking distance to Tacolicious, we knew we had to go get some of their famous ice-cream. Bi-Rite offers homemade organic ice cream and the flavors were exceptional. It was one of the best ice-creams we’ve had!
We learned from our previous night that dressing down was the key to having fun in SF at night. So tonight, we made sure we were dressed more casual and ended up at a pirate themed bar, called Smuggler’s Cove. The bar is kind of hidden – with an unmarked door and a low-key feel to it. Once you enter, you will be greeted with a pirate ship decor and tiki-style drinks (warning: these drinks are pretty strong!).
Day 4: Napa Valley – Chateau Montelena Winery, Castello di Amorosa, Domaine Carneros
Tina and I both love wine, so naturally, we had to take a quick trip to Napa! We rented a car and after a quick stop at Philz Coffee (mint mojito coffee anyone?!), we were on our way to the vineyards. To make sure that we weren’t rushed, we decided to visit only 3 wineries with a break for lunch in the middle.
The first winery on our list was Chateau Montelena, one of the oldest wineries in Napa, known for its award winning Chardonnay. Apart from the great wines, Chateau Montelena also has beautiful, picturesque grounds – stone castle, Chinese garden, and a lake. We walked into the tasting room and were greeted warmly by a sommelier, who explained the history and properties of each each wine. After finishing our set of tastings (and being a little buzzed), we roamed outside to enjoy the view and take a few photos.
We’ve actually visited Castello di Amorosa on our previous trips to Napa but we can’t help but visit this castle every single time. Driving up to this winery, we immediately feel like we’ve been transported to the Tuscan hills of Italy (or if you’re a Game of Thrones fan – in King’s Landing). The courtyard is stunning and the wine here is our favorite (Tina especially loves the sweet dessert wine, La Fantasia). You can choose to do a tour+tastings (which we recommend if it’s your first time), or just do the tastings by itself.
After two sets of wine tastings, we were definitely ready for lunch (especially carbs!). We wanted something quick and easy since we wanted to make it to one more winery before sunset, so we headed over to V. Sattui Winery. This winery has a deli that serves delicious sandwiches, pastas, salads, and cheese & crackers, that you can enjoy on their picnic grounds. It is one of the few places near the wineries that serves “real” food other than cheese plates. We grabbed fresh paninis and enjoyed the Napa sun as we ate.
We ended our day at Domaine Carneros, partly because they specialize in sparkling wine, and also because it was the closest to our hotel in Napa. It’s also a gorgeous winery, complete with French-style mansion, that’s apparently a replica of the owner’s home in France. Since the mansion sits up high, we were able to watch the sun set over the vineyards as we sipped on some champagne.
Day 5: Napa Downtown, Brunch, Travel Home
On our last day, we quickly packed up and spent the morning walking around downtown Napa and visiting the boutiques and shops. Downtown Napa is such a cute area with an old-town vibe and we highly recommend you spend time visiting this area if you get a break from the wineries!
What better way to end the trip than brunch? Before we headed to the airport, we stopped at Grace’s Table to enjoy the delicious food, including their amazing iron skillet cornbread with lavender honey butter (so yum!).
We hope you found this helpful! Have you been to SF and Napa? Let us know your recommendations below!
-Tina and Shreya