A Weekend Guide to San Francisco

A couple of weeks ago, Finn and I headed to San Francisco for a much-needed getaway. We were actually in Las Vegas for a few days for the National Hardware Show and figured as long as we were all the way on the west coast we might as well check out another city after work was over! weekend guide to san francisco

While I’ve visited San Francisco before (I actually had my bachelorette party in Sonoma a few years back), Finn has never even been to California – at least as an adult. (I think he came one time as a toddler!) So we figured now would be the perfect time to check out this amazing state together. Our weekend guide to San Francisco, California

I had so much fun sharing our adventures on Insta Stories and I got some amazing feedback from you guys while we were there. I saved all of those adventures on a “San Francisco” highlight on my Instagram profile if you want to check that out.

Weekend Guide to San Francisco

weekend guide to san francisco

Whenever I’m planning a trip, I now ask you guys ahead of time for your recommendations and suggestions on where to go, what to eat, where to stay, etc. While we weren’t able to check out every spot you sent our way, I’ll definitely share all of the amazing recs you gave me from Instagram. Hopefully, this weekend guide to San Francisco helps as you plan your upcoming trip to this awesome city!

Where We Stayed

We ended up staying at Hotel Spero in Union Square. I wanted a place that was centrally located and Union Square is kinda smack dab in the middle of the city. The hotel itself was really nice and the decor was on point. Gotta love a boutique hotel with cool vibes.

If you’re familiar with San Francisco, you’ll know that there is a bit of a housing crisis and therefore there are lots of homeless people on the streets. This area was actually pretty full of homeless people and we were a bit surprised when we arrived. While I wouldn’t discourage you from visiting that area (we never felt unsafe), it’s just something to keep in mind.

Maybe a local will be able to chime in in the comment section with a better suggestion on the best area to stay in town when you visit.  If I had to do it all over again, I’m not totally sure which area would be best for us, so I’d love to hear your recommendations.

Where We Ate

Whenever Finn and I go on vacation, we always eat our way through the city, tapas style. For us, that means we never really sit down and have a huge meal. Instead, we’ll just get an appetizer here, and a drink there. Then we’ll split an entree at our next location, so on and so forth. We love doing this because it allows us to try out more places and experience different cuisine, and we’re never left feeling overly stuffed and in need of an afternoon nap (no food comas allowed on vacation!).

It’s funny because a few of you guys mentioned on Insta Stories that it felt like we were just doing a big food tour of the city, which is partly true! We love to eat and drink on vacation, all the while walking everywhere (so we can burn off a few of those calories). Here are a few of the spots we checked out during our three days.

    • Matador: This was close to our hotel, so we popped in here for happy hour one day. The margaritas and chips and guac were phenomenal!

the buena vista in san francisco

  • The Buena Vista: So many of you guys recommended this spot, so we had to check it out! It’s by the water and it’s an old-school bar with fun drinks. Make sure to order the Irish Coffee (it was heavenly!).
  • Lou’s Fish Shack:  A little touristy, but we ate clam chowder in a bread bowl and it was yum!Baked bear in San Francisco
  • Baked Bear: Holy smokes, this was the cutest little ice cream shop ever. All of the ice cream sandwiches are made to order, so you can choose your cookie, ice cream flavor, and the toppings. It was absolutely delicious!
  • Philz Coffee: Another spot that came highly recommended (and I’m extra excited because we’re getting one of these in our neighborhood in Chicago!). The coffee was so unique and they had yummy breakfast options (I got the avocado toast and it was a  great way to start the day).
  • MarketBar: This cute restaurant is in the Ferry Building (a must-see!) and we sat outside enjoying fresh seafood.
  • Mission Cheese: We were still full from our lunch, so we didn’t get any cheese but their cheese boards looked delectable. Instead, we got a cold glass of vino here.cookie from tartine bakery
  • Tartine Bakery: Lots of DMs to check out this place and it did not disappoint. I got a chocolate chip cookie, but their other desserts were just as mouthwatering.
  • Oracle Park: Seems random to put a baseball stadium on the list, but I was so impressed by their food selection. I ended up getting the “Cha Cha Bowl” which was a yummy chicken bowl with veggies (surprisingly healthy for a baseball game). We also got the garlic fries and warning… we legit smelled like garlic for two days! But I’ve got to say…worth the stink! haha. Prosecco at barbocce
  • BarBocce: One of our friends recommended this spot in Sausalito and it was adorable. While the bocce court was full, we still enjoyed our time drinking cocktails in the sunshine, gazing out at the water.Ceviche for lunch in sausalito
  • Barrel House Tavern: The yummiest lunch of the trip was at this restaurant in Sausalito. We ate outside and split the ceviche, flatbread, and snapper sandwich. I’m not sure if we were just starving, but every bite tasted unbelievable!


Your SuggestionsGhirardelli in San Francisco

  • Ghirardelli – “Split a giant sundae.”
  • Souvla – “Best Greek food I’ve ever eaten.”
  • La Boudin
  • La Taqueria
  • Neptune Oyster
  • Osso Steakhouse
  • The View for a Drink – “The views are incredible!”
  • Trattoria Contadina
  • Farmhouse Kitchen – “Unique Thai food”
  • Nob Hill Cafe – “Best little Italian restaurant in a great neighborhood.”
  • Toast – “Great breakfast spot.”
  • Pompei’s Grotto
  • Mini Donuts on Pier 39
  • Hog Island Oyster Co.
  • The Slanted Door *lots of recs for this one!
  • Burma Superstar
  • Il Casaro – “Great pizza!”
  • Nopa Restaurant
  • Drinks at the top of the Mark
  • Scoma’s Restaurant
  • Flour & Water
  • Nick’s Lighthouse
  • The Stinking Rose *lots of recs for this one!
  • Salt & Straw – “Best ice cream”
  • Kokari – “Best Greek food in the city.”

What We Did

boats in Sausalito

We weren’t able to cross everything off our San Francisco to-do list (never got around to seeing The Painted Ladies), but I feel like we did cover a lot of ground in the 2.5 days we were there. First of all, we walked everywhere! It’s a big town (with lots of steep hills!), but I love exploring a city on foot. You just never know what you might discover as you stroll along the city streets.Alcatraz island

Here are a few of the spots we hit up.Chinatown in San Francisco

    • Chinatown: This neighborhood is huuuuuge and it’s really fun to walk through. They have Chinese markets, storefronts, and the coolest wall murals in this area. Definitely walk through it.Lombard street in San Francisco
    • Lombard Street: This is the famous twisty-turny street that you’ve probably see in the movies. Worth a stop for a cute pic!Pier 39 in San Francisco
    • Pier 39: The Fisherman’s Wharf area is a bit touristy, but it’s a must-see.  And don’t forget to stop at Pier 39 and check out all of the seals sunbathing. It’s smelly, but also incredibly hilarious to see them lazing around and making tons of noise!
    • Washington Square: There are lots of cool restaurants in this area (lots of good Italian ones) and we wish we had more time to really enjoy this cool park.Finn enjoying the trolley
    • Trolley Ride: You’ve got to take a trolley ride at least once during your San  Fran trip. Did I sing the rice-a-roni song the entire time? You betcha!

Weekend guide to San Francisco

  • Visit the Ferry Building: The Ferry Building was such a neat spot full of unique restaurants and local shops. They even had a farmer’s market happening there on Saturday. Definitely check it out, especially for a yummy snack!finn in front of a wall mural
  • Bike Ride to Mission District: A lot of the restaurant recs you guys sent our way were for the Mission District area of the city. It was about 2.5 miles from our hotel, so we ended up biking over there. Lots of street art, cute shops, and cool bars in this area.
  • Mission Dolores Park: This is near Tartine Bakery, so we ended up getting some goodies and enjoying them in the sunny park.Oracle Park stadium
  • Baseball Game: While I’m not a huge sports lover, I absolutely love going to all kinds of sporting events. It’s just so fun to check out a new stadium, eat some food, and take in the sights. Oracle Park is gorgeous because it’s right on the water and you’ll even see people kayaking in the water waiting for home runs!
  • Alcatraz Island: This was on the very top of our to-do list and I’m so happy we visited this San Francisco attraction. While it was a bit creepy to tour this old prison, it was also incredibly fascinating. We opted for the free audio tour and it was so well done.  They also offer a night tour, but I’m way too big of a scaredy-cat to ever do that!

    Visiting alcatraz island for weekend guide to san francisco

    • Travel Tip: Be sure to book your tickets well in advance for Alcatraz as it fills up quickly. We booked ours about a month out and had no trouble getting an 11 am ferry on a Saturday. Ferry ride to sausalito
  • Ferry to Sausalito: We had every intention to bike across the Golden Gate bridge over to the Sausalito area of the city, but we didn’t get back from Alcatraz until 1:30 pm and wanted to make the most of our Saturday. Instead, we took a 30-minute ferry across the way to Sausalito. We purchased a round-trip ticket in San Francisco at the Ferry Building and it was incredibly easy both ways! Plus, the views from the boat are stunning.
  • Walk Around Sausalito: Our favorite afternoon was spent exploring Sausalito. This cute town is full of colorful homes, quaint shops, and yummy restaurants. I highly recommend carving out a day for this. We wish we could have had more time there! Next time, we’ll definitely try to bike across the bridge super early and spend our entire day exploring Sausalito.


Your Suggestions

  • Muir Woods – “The redwoods are amazing and it’s very peaceful.”
  • Walk the Golden Gate Bridge
  • Botanical Gardens
  • Drive to the Sequoias
  • Japanese Tea Garden
  • Penny Arcade on 45
  • Angel Island
  • Visit the Painted Ladies (I’m sad we didn’t fit this into the trip!)
  • Urban Putt – “Indoor mini golf with adult beverages.”

What We Packedwhat we packed for our trip to San Francisco

Casey riding the trolley in San Francisco

If you take one thing away from this post, it should be this…pack allllll the layers for your trip to San Francisco. The weather is bonkers (at least in early May). One minute you’re sweating in the sunshine, the next you’re reaching for your jacket to bundle up. Even though the weather app said 60 and sunny every day, it was all over the place. The wind and the fog make 60 degrees feel a lot cooler than 60 degrees in Chicago. Trust me.

I wish I would have brought more sweaters and maybe even a heavier jacket. I also packed a few dresses that I didn’t wear (between the wind and the cold there was just no way!).  Finn donned shorts the first day and he was freezing his tush off! Finn wearing t-shirts in San FranciscoHere’s what I suggest packing…

  • Jeans: I brought black, white, and regular. I never wore shorts.
  • Jackets: I brought my favorite utility jacket and this jean jacket. I wish I would have packed my leather jacket too.
  • Gym Shoes: Omg, an absolute must! We walked miles and miles every single day. I brought cute heeled sandals that I never wore. I did wear flat sandals during the day, but cute gym shoes would have worked fine (like my favorite blush ones!)Wearing white jeans in San Francisco
  • Crossbody Bag: So you can be hands-free as you explore.
  • Sweaters: I only brought one to wear to the baseball game and wish I would have packed a few more.
  • T-shirts: I was very casual throughout the entire trip and mostly wore my favorite v-neck shirts underneath my jacket. That way if it warmed up I could ditch the jacket and feel perfect!
  • Hat: I wore a baseball cap to the baseball game, but ended up wearing it for other parts of the trip too. It came in handy on the ferries when my hair was whipping around like crazy! Definitely add a hat to your suitcase. (I got lots of questions about my gray cap on Instagram and sadly it’s super old from Nordstrom. But this one is super similar!)
  • Sunglasses: I packed my favorite black sunglasses (I get tons of compliments on these).

Casey and Finn at the baseball gameIf you do go to Oracle Park for a game, bundle up! It was super windy and brisk right on the water and we both wished we would have packed warmer items for the game.

Until Next Time, San Francisco!

Weekend guide to San FranciscoSan Francisco Palm treesCasey and Finn in San Francisco

Overall, it was a trip to remember! And we definitely need to make it back to explore more gorgeous cities in California. Hope this weekend guide to San Francisco helps you plan your next trip! Let me know in the comments below if I missed any must-see activities!



The Year of Casey

Hey there!

I’m Casey Finn, the voice behind The DIY Playbook. I’m a Chicago gal teaching you how to design, DIY, and maintain your home…by yourself! Learn more about me right here.

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