How to Strategize Your San Francisco Vacation

 There is so much to see in San Francisco between Alcatraz, Fisherman's Wharf, the Fine Arts Palace, Land's End, Golden Gate Park, and so much more! Trying to see it all while on vacation requires a game plan. So I want to write this post to help you strategize (as best I can) your visit and get the most out of your stay in San Francisco. - The Confused Millennial



Home to the Tanner clan!

I absolutely love San Francisco.  I went as a kid and remember really enjoying it, to this day it was one of my favorite vacations growing up. The red wood forests! The Painted Ladies! The Golden Gate! Fisherman's Wharf! The Cable Cars! I thought it was so cool when I was little.

Now going back with my fiance, who has never been, I tried to see as much as possible but I really did a poor job planning and we spent a lot of time back tracking to part's of the city to see one thing we missed in that area… talk about a waste of time!

Seriously, there is so much to see between Alcatraz, Fisherman's Wharf, the Fine Arts Palace, Land's End, Golden Gate Park, and so much more! Trying to see it all while on vacation requires a game plan. So I want to write this post to help you strategize (as best I can) your visit and get the most out of your stay in San Francisco because there is A LOT to see (a lot I still haven't even seen!!).

– Book your trip to Alcatraz ASAP! I went as a kid, and just kind of assumed that my mom had us go when we were there… but nope, you need tickets like a month or two in advance! Unfortunately, this trip we did not see Alcatraz. I loved it as a kid, though! So I would definitely say get those tickets early!


san francisco alcatraz rachel ritlop


The city is all over the place with clusters of lot's to do/see in different little areas. We did not do any guided tours or tours buses, we used Uberpool everywhere (when I crunched the numbers it was way cheaper Uberpool than buy two tickets on the bus tours.

We were staying in the Castro District (pretty much the bottom center of this map below). I am going to start around Castro, then work from South East(ish) to South West(ish) I am going to do my best to give you the most efficient way around the city so you don't have to back track to the same area on various days because you missed something (like we did….oops!):


san francisco rachel ritlop


Castro District is considered the LGBT heart of the city.

We ate at a couple of places here since it's where we were staying:

1) Frances.  They have applewood smoked bacon beignets that are to die for! Chickpea fritters (Panisse Frites) with the most delicious dipping sauce! A salad special that night and Honey brined pork chop.  The salad was okay, nothing special and same with the pork chop. What upset me was that they added a sharing charge of $8 because we only got one formal entree (but, um, hello we had three appetizers!). So because of that, and the fact it's generally pricey with no real standout entrees, I would actually recommend skipping it, unless you are going to just get apps there and go somewhere else for dinner.

2) Kitchen Story. AMAZING! Again on the pricier side of things, but seriously it's worth it. This place super cute and delicious. We split the BEC (Maplewood bacon, egg, and white cheddar cheese melt) and the New England Burger (maple syrup wagyu patty with millionaire's bacon, arugula, and white cheddar) which was probably top 5 favorite burgers I've ever had. I think we may have gotten a fried egg on it too… I can't remember. The food was great, coffee was delicious, and it was so cute.


san francisco rachel ritlop


Next up is Mission District.

Mission District, aka The Mission, is a really cool district. It's extremely diverse. Some parts are beautiful and other parts (according to my friends who have lived there) you can hear regular shootings. It's fun to walk around and see all of the different art/graffiti and culture, but the best part about the Mission in my opinion is Dolores Park. Dolores Park is huge and offers beautiful views of the city line and Bay in the distance.



The biggest thing I feel like we missed out on in the Mission was a stop at La Taqueria. EVERYONE (from friends to Uber driver's) recommended it.

From Dolores Park I would recommend walking the mile over to the Painted Ladies.


painted ladies san francisco


From the Painted Ladies I would recommend starting to head north east towards the Westfield shopping center on Market St and Union Square. This is such a great area if you are looking to splurge, they have a great variety of affordable and high-end stores in the shopping center and along Market street in this area as you continue walking north east more towards the Financial District.


While you're in the Financial District and walking over towards the Ferry Building, I would strongly recommend stopping at Philz and getting a mint mojito (despite the name it does not come with alcohol) coffee. Seriously, this is like the most delicious coffee I have ever had. They have other delicious one's if you're not a mint person. My fiance had the mocha tesora and it was just as amazing.

From Philz you are just a couple of blocks from the Ferry Building. Enjoy the views of the Oakland Bay Bridge. While you're in this area too! The Ferry Building has some cute shops and places to eat and people watch.

san francisco


We had lunch with the amazing Veronica Chung at Out The Door which is a spinoff of Charles Phan's nationally acclaimed Vietnamese restaurant, The Slanted Door (located in the Ferry Building too I think on a higher level). The crispy imperial roll was outstanding!


san francisco


Also near the Financial District (although not quite along the coastline like the Ferry Building) is House of Nanking. You must stop here for some of the most delicious Chinese food I've ever had! It's so clean. The tables are kind of weird, and you will probably end up sitting with other people, but I have to say I was so impressed. Better than any Chinese restaurant in NY I've been too (but you guys know I am not a fan of NY so I might be biased haha). But even my fiance who grew up in NY and lived there for 25 years agrees it was amazing!

From the Ferry Building I would walk along the coastline towards Fisherman's Wharf. The mistake we made our first couple of hours there was head straight for Fisherman's Wharf. Bad move. It's smack in the middle of things you want to see, so I would either start at the Ferry Building and work my way west or Fort Mason and work my way east.


Around Fisherman's Wharf make sure to check out the antique arcade, shops, sea lions (if they are out!) at pier 39, and embrace the gorgeous views coming at you from every angle!


If you are starting from Fort Mason and working your way East, I would stop at Lombard Street and then work my way down to Ghiradelli square and the coastline.


Otherwise, if you are down by Fisherman's Wharf and Ghiradelli square, make sure to head a mile south on Hyde Street or Leavenworth Street to check out the famous Lombard Street.


Continuing with our east to west direction… from Fisherman's Wharf / Lombard St / Ghiradelli Square area, head past Fort Mason, the Marina Green, until you hit The Palace of Fine Arts Theatre. This is a must see it's so gorgeous. Also sign up in advance for the escape the rooms inside.



From The Palace of Fine Arts it's 2 miles towards the Golden Gate Bridge Welcome center and Fort Point.


This next part is my absolute favorite part of San Francisco. From Fort Point we walked about 4.5 miles through Helmet Rock, Baker Beach, the adorable Sea Cliff town, Land's End, to the Sutro Baths (which unfortunately were closed by the time we got there – but basically they are these public baths built in 1896, now the baths are still active and you can see the historic ruins).



One thing we missed on that hike was seeing the Labyrinth! I was so upset we missed it! Every single random beach walk you could take to explore we did except this one because we had already walked 10 miles earlier that day before taking on this last 4.5. GRRR! Anyway when you see the sign for Mile Rock Beach do it!! Take the little path and send me photos! I hope to make it back there someday to see this.


[tribulant_slideshow gallery_id=”9″]


I know this post was packed with places to see and information, but the crazy thing is, I missed SO much! Aside from Alcatraz and the Labyrinth in Land's End, I also missed the Japanese tea garden in Golden Gate Park and the Twin Peaks hike between the Castro District and Noe Valley.


Have you ever been to San Francisco? what are your tips?

Ready to fulfill all of your Wanderlusting dreams?

Download TCM's guide for saving on a tight budget!