5 Days in San Francisco


Day 2: Civic Center, Painted Ladies & The Mission

San Francisco City HallThe next day of our 5 days in San Francisco involved a lot of walking but would totally pay off. We started with a visit to the nearby Civic Center, a large and open complex of civic buildings (library, opera house and city hall). Strolling around the civic plaza feels like walking around Rome, as magnificent Classical building are all around you. However, this area is also home to many of San Francisco’s homeless population, a stark contradiction. You can’t really miss the San Francisco City Hall, it’s dominant at the center of the plaza with its gold dome, quite impressive. Completed in 1915, this building was also the site of the 1978 murder of Mayor Moscone and gay activist Harvey Milk.

Next up was climbing Fulton St. towards Alamo Square. This gave us a glimpse of what’s to come – beautiful pastel-colored Victorian houses, that are immediately associated with San Francisco. As you reach Alamo Square, you won’t be able to miss the Painted Ladies, a row of Victorian houses with the city’s skyline in the background – famous from postcards, movies, and television shows.

Painted Ladies San Francisco

We then headed back down the hill on Steiner St. and stopped at the lovely Duboce Park Cafe, just across from Duboce Park. This cafe has outside seating and on such a sunny day, after climbing up to Alamo Square, we stopped to relax and catch some sun.

  • Ike's Place San Francisco

Continue down on Sanchez St. until you hit 16th St. and you’ll probably see people queuing up. This is Ike’s Place, a legendary sandwich place in San Francisco. You can call ahead of time and pick up your choice but queuing up gives you a chance to go over the extensive names on the menu such as the Fat Bastard, Al Bundy, Heath Ledger or perhaps the Menage a Trois. The sandwiches here are fresh and fabulous (and quite filling). I had the Elvis Keith, a delicious combination of chicken, teriyaki and wasabi mayo – on a dutch crunchy bread. Wait for your name to be called and in the meantime, enjoy a complimentary bag of hipster style potato chips. But wait – don’t eat your sandwich yet.

Mission Dolores San FranciscoJust a block down the road on 16th St, you can’t miss an impressive classical Spanish basilica. Dwarfed next to it is a tiny adobe church – this is Mission Dolores ($5 entrance) and the 1776 birthplace of San Francisco (or Yerba Buena as it was called back then). This was the first European settlement in the area, on the site of what was then a creek. Mission Dolores also gives its name to one of the coolest neighborhoods to explore in San Francisco – The Mission.

The Mission district is comprised of Mission and Valencia Streets. Though running in parallel, these two streets couldn’t be more different. Mission St. is strikingly Hispanic while Valencia St. is hipster central. This mix of cultures, in a neighborhood that has always been dominated by immigrants, is what gives The Mission its cool flavor and makes for a pleasant stroll. Like Chinatown and North Beach, it’s yet another example of how diverse San Francisco is, in a matter of a couple of city blocks.

We didn’t forget about the sandwiches from Ike’s Place, hard-earned through 20 minutes of wait. We just waited for the perfect spot to have them. That place is Dolores Park, a favorite gathering spot for Mission residents and you can understand why. Dolores Park offers a superb escape from the city, with wide green areas and great city views from the southern end. Along with fellow sunbathers and guitar players, we grabbed a spot on one of the hills to enjoy lunch with a sunny and unobstructed view of San Francisco.

Dolores Park San Francisco

Dolores Park San Francisco

With our stomachs full, it was time to explore The Mission. A good way to head down towards The Mission is via 20th Street. Starting at Dolores Park, this street boasts a great variety of lovely Victorian houses, each with its own unique character.Taqueria San Francisco It’s also relatively quiet here, so different from other parts of town. Because there are no famous landmarks here, not too many tourists venture out to this area and it feels pretty local. We stopped at the corner of Mission St. to explore the Hispanic area first, turning left and heading north on Mission. This street feels rough and vibrant: pawn shops, fruit & vegetable markets, tobacco shops, tattoo parlors, Latin music in full volume from passing cars and of course – a great number of taquerias. Though some recommend avoiding certain parts of Mission Street, we didn’t feel unsafe, and its rough atmosphere was quite cool to suck in. We wished we had some appetite left for burritos as some of the city’s best can be found here.

After a few blocks, you’ll see to your right a tiny but colorful alley, lined up with hundreds of murals. This is Clarion Alley. You might also recognize it by the smell of urine as this place is a bit rough. It’s a good spot to cut west through the alley towards Valencia Street and marvel at some of these remarkable pieces of urban art, usually with a political or cultural theme. More on San Francisco’s famous murals in a bit.

  • Clarion Alley Murals San Francisco

At the end of Clarion Alley,  turn left onto Valencia St. and San Francisco’s ‘hipster central’. Valencia St. couldn’t be more different than its parallel neighbor. This street is made for walking, filled with good ethnic restaurants with a hipster twist, cafes, boutiques, music shops, vintage shops, and specialty shops. If you’re wondering what’s that funny smell in the air, well it’s probably Marijuana (‘weed’ as it’s commonly referred to). It’s San Francisco after all… The atmosphere here is very pleasant and it’s just fun to explore. A good stop for book lovers is Dog Eared books, with a really cool selection of international titles, second hand, and photography books.

  • Dog Eared Book The Mission

Once at 24th St. and Valencia, make a left and walk towards Balmy Alley. On the way, we stopped for some for cardamon tea at Cafe la Boheme, a really cool spot with a good lite menu – quite popular with youngsters on Macs who seem to be working from here on the next tech startup. Another good refreshment option is Philz Coffee on Folsom St. This place regularly receives top awards for its blends and is very popular.

  • Philz Coffee San Francisco

Just a few meters after Folsom, make a right onto Balmy Alleythe best place to admire the Mission’s murals. It’s a lot more pleasant to view the murals here than on Clarion Alley. Local Latino artists have been painting here since the 1970s, depicting Latino life along with their hardships through this beautiful art. The rising real estate prices in San Francisco have forced many out of the neighborhood and the frustration is vented through art in Balmy Alley.

Balmy Alley Murals San Francisco

If your muscles aren’t aching by now and you’re in the mood for another adventure, head back to Folsom St. and keep heading south. You’ll enter the neighborhood of Bernal Heights, a quiet place with a village feel. Its beautiful houses are perched on a steep hill. Residents must either have strong leg muscles or very powerful cars. Continue climbing up Folsom until you reach the entrance to Bernal Heights Park. Trust me, you’ll be rewarded.

Bernal Park 5 days in san francisco

Follow the path and soon you’ll be treated to breathtaking views of the city, with the mission below, the bay to your right and the city’s skyline just in front of you. It’s a great spot to sit back and relax after all that walking. You can actually walk around the hill and gain different perspectives and if you’re feeling even extra adventurous, get off the path and climb to the top of the hill (where the radio tower is) for an even better view. What a way to finish off the day! As a tip, watch out for the fog that will probably start to roll back in (just look to the west) around 5-6pm and time your visit accordingly.

Le Colonial San FranciscoAfter a nice rest, we made our way down and after a stop at Taqueria Can Cun for some ever refreshing Horchata (sweet Mexican drink). The BART conveniently runs below Mission Street and we took it all the way back home.

For dinner, we headed to Le Colonial on Cosmo Place for some French Vietnamese cuisine. Well decorated on the outside, with a lush garden entrance, the interior is just as appealing and colonial in feel with traditional ceiling fans and tiled floor. We started off with some cocktails, The Spice of Saigon and a mojito. For starters, we had some delicious vegetable rolls and for mains – tuna steak and lemongrass chicken in coconut sauce ($100 not including tip).

Any Regrets?

  1. The Mission is filled with excellent taquerias and Mexican restaurants. Among them: Papalote, Es Castillito, and La Espiga De Oro. We would have loved to visit at least one of these but we were quite full from the excellent sandwich at Ike’s place.
  2. Another great spot for a San Francisco view is at Twin Peaks, which commands a great view of the city, just above Market Street. A visit there goes well with exploring the Castro district, which is quite close to Mission Dolores. The Castro is the city’s LGBT hotspot and we were recommended to pay a visit. We simply didn’t have the time and I think this area actually deserves its own day.


  1. hi! we’re goin on a trip in august and i love your recommendation for biking over the Golden Gate to Sausalito ..but if we bike there,is there a place to drop off the bikes so we can take the ferry back over? ..i missed that in case u mentioned..
    ps thank you for your trip itinerary! VERY helpful!!

    1. Hi Stephanie!

      Thanks for the feedback, glad you find it useful! Nothing keeps me more motivated to continue writing that fellow travel readers joining the newsletter 🙂

      As for your question, the Sausalito ferry is very bike friendly so you’ll actually take the your rented bike on the ferry. It’s all very organized.

      Have fun in SFO and don’t forget to pack some warm clothes 🙂

  2. Hi Avichai,
    I’m planning a vacation for my family in September in California. We plan to fly into San Diego and drive to San Francisco making our way through important points such as disneyland, LA, coasts, etc.
    I’ve started with planning the San Diego side of the trip and there are so many things we want to do there that I was planning to give it 5 days (Seaworld, zoo, safari park, USS Midway, Coronado, etc, etc) [Your post was very helpful btw!] I was only planning for 1-2 days in San Francisco but now that I see you took 5 days there I’m a little confused. Do you think we should spend less time in San Diego and more time in San Francisco? We want to go to the parks as well as the beaches!

    1. Thanks for reaching out. I can understand why you would want to spend this amount of time in San Diego. There’s more family stuff to do there with the Zoo, Seaworld etc. I think 5 days might be a bit too much though, depending on how old the kids are and how quickly you can get from place to place. Keep in mind that you’re talking about a very long drive with both L.A and the PCH on the way. Since I spent a lot of time in San Francisco, I got to see a lot of it. I wouldn’t think places like The Mission, Golden Gate Park & Chinatown are musts if you’re on a family trip with young children so perhaps 3 full days in SFO are OK. I would say the musts in SFO are: crossing the bridge, Fisherman’s Wharf area (for the kids), Alcatraz, a bit of nature (Muir Woods) and a bit of walking around. So to make a long story short – if the kids are young and you’re looking primarily to entertain them, your plan seems to be right. Maybe just reduce SD by one day. Have a great trip and feel free to ask anything else!

  3. Great guide! I used to live in San Francisco and it always makes me sad that tourists waste their time going to Pier 39, which only contains restaurants and stores you can find all over the US, if not the world. That being said, I guess I don’t really understand the tourist mentality having lived there. To add to your list: hiking Land’s End, exploring the Presidio, Lyon Street steps in Pacific Heights for some beautiful views and breathtaking mansions, walking down Clement Street in the Richmond, shopping and dining on Fillmore Street, California Science Academy in Golden Gate Park, and taking a tour of the Anchor Steam brewery (with free tastings – must reserve in advance).

  4. Hi there. Great info and so thoughtfully laid out! My husband is travelling to SF for work the first week in March and my 13 month old daughter and I are going to join him. We get a Tuesday-Friday, just the two of us, to explore and have an adventure, then will be staying Friday-Sunday with my husband not working so we can enjoy the area as a family. I feel confident that we can do most of what you suggested and am so excited. The only part that’s a bummer is the biking, because she’s just too young to haul around in a bike trailer. I wear her and have a lightweight, very fold-able stroller. Any tips for substituting the biking with a combo of walking and public transit? Perhaps other travelers with small children would gain some insight from this as well. Again, great post!

    1. FYI, we are staying in near Fisherman’s Wharf the entire time. Tues-Fri my husband will be working, so it’s just the baby and myself exploring. Friday night through Sunday night (taking a red-eye home, so have all day Sunday as well) my husband will be off work and joining us.

  5. Thank you so much for this post. I just came back from San Francisco and it helped me so much, basically I did everything you have in this itinerary and I really I felt like I didn’t miss a single thing of the city.
    You should do this to every other city in America!, this guides help us so we can avoid wasting time in the middle of our trip asking ourselves what can we do next.

    1. Thanks so much Madeleine!

      I’m glad you found the itinerary useful. Working on getting more published, so stay tuned, and tell your friends 🙂

  6. Hello, do you have a recommendation re. where to stay/what area is a good central location, if a family with teens is planning to do this itinerary?

    1. Hi Shannon

      You can’t go wrong with Union Square area hotels. Though on the expensive side, the location is central and you’re close to everything. Another option is by Fisherman’s Wharf. There are lots of family hotels just behind it. Airbnb has a lot of options if you’re comfortable with that. For the ‘real’ experience, you can find a place in Nob Hill or Russian Hill (though you’ll have to negotiate the hills). I put a few recommendations for hotels I stayed on the second page. Enjoy!

  7. Hello Avichai,

    Considering your 5 day itinerary, do you think is usefull to take a hop-on hop-off bus service? or your itinerary considers to walk and use of public transportation to reach every spot.

    I am going to stay 5 1/3 days in SF and your itinerary looks fantastic. Let me know your opinion.

    Thanks in advance


    1. Hi Ricardo

      I used the trams to get down to fisherman’s wharf, subway to get back from Bernal Heights and cable car to get back from that day of cycling. We did a lot of walking though (a lot), which is something I enjoy very much. My friend who went with her mom to SFO (who can’t walk so much), did the hop on / hop off bus and it was ideal for them. The bus does stop at all these attractions and if you don’t want to use public transportation, it’s probably a convenient thing to have. Let me know if you have more questions and have fun in SFO!

  8. Hello,
    We’re coming from New Orleans to SFO and Napa. Our first time visiting.
    Any suggestions for our trip there? We’ll be staying 6 days and would like to do the wine train and coast as well.
    Thanks in advance for all info.

    1. Hi Beverly

      If it’s your first time in the area, I would recommend doing a combination of days 1,3 & 4 from this SFO itinerary http://xdaysiny.com/5-days-san-francisco-california-itinerary-guide/ and days 2 & 3 in this Pacific Coast Highway itinerary http://xdaysiny.com/3-days-pacific-coast-highway-california-road-trip-itinerary-guide/ Napa Valley requires one day from SFO and simply means one person will need to be the designated driver. It’s a bit tight to squeeze everything in 6 days but possible. Enjoy!

  9. Hi Avichai,

    Really interesting subjects covered. Thank You

    Me, my wife and two kids (2 & 4months) are staying in fremont with family and plan to visit SF in three days. Few questions we had was how to travel (Car back and forth or bart train ) We are not staying in SF so would visit , see sites and come back to fremont each day. Can you suggest some itenaries and also how with kids one would reach from one point to the other (For eg Union Square to Fishermans Wharf ). Further down we will drive down to LA from fremont and spend 5 days there (staying in a hotel). and then moving to San Diego for 3 days and back to fremont.

    1. Hi

      So normally I would suggest to take the BART and then Uber around town but you need car seats… If that’s not an issue then you can probably leave the car behind and avoid the parking fees in town. As for itineraries considering you have small infants, that’s difficult for me to say b/c I don’t know how comfortable you are carrying the kids around. However, I would say that Golden Gate Park, Crissey Field area (waterfront + Golden Gate Bridge), Fisherman’s Wharf area (watch the seals), Bernal Heights (get a ride there), Alcatraz – are all sites that you can enjoy as a family (Alcatraz is probably more for the adults). You could also check if Blazing Saddles rents bicycles with child seats or small ‘carriages’ in the back and then enjoy what is (for me) the highlight of visiting SFO – riding across the Golden Gate Bridge. If you do have a car, you can also check out Muir Woods. Hope this helps. Enjoy!!

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