5 Days in San Francisco


Day 1: Union Square, Chinatown, North Beach & Telegraph Hill

Lotta's Fountain San FranciscoWe arrived the evening before and conveniently stayed in an apartment on Market & 10th St. It’s not the best part of the town at the moment, especially at night. A taxi from the airport can set you back $45-60 and in rush hour, can be a lot more. Instead, we took the BART from the airport directly to the Civic Center stop, paying only $8.75 one way and taking about 30 mins.

The following day, we headed out to explore the downtown area of San Francisco. The first stop was Lotta’s Fountain, at the corner of 3rd St. Named after actress Lotta Crabtree, this now decommissioned fountain, served as a gathering spot after the devastating 1906 earthquake. Market St. is also a great place to see some of San Francisco’s railway cars (not to be confused with the cable cars). These railway cars were actually bought by Muni from other U.S. and world cities, restored, and put in service within the city. Each car is uniquely painted and you can read about its origin on board.

Street Cars San Francisco

It was time for breakfast and we headed to Union Square and Sears Fine Food on Powell St. just across from the famous Sir Francis Drake Hotel. Aside from the signature meals this place has been serving since 1938 (including the famous Swedish pancakes), it’s rich with old San Francisco history and you’ll see right when you walk through the door. Ceiling fans, wooden decor, and tiled floor tell the story of this place and hundreds line up here each morning (breakfast served until 3 pm). We had the eggs benedict on English muffin and a vegetarian omelet with hash browns – delicious! At the end of your meal, spin the slot machine on your way out for your chance to win some yummy prizes.

Sears Fine Food San Francisco

Next up was Union Square, San Francisco’s major shopping spot. The square itself is lovely to walk through (or skate through in the winter) and surrounding it are dozens of shops and hotels. You’ll find here luxury brands like Tiffany’s, Coach and Burberry, but also more down to earth shops like Nike, Levi’s, DSW and of course, Macy’s. Macy’s Union Square is actually made up of two buildings, one for men and the other for women. If you’re visiting from outside the US, be sure to get your visitors pass, which will give you a 10% discount at Macy’s. Be sure to also make your way up to the top floor and to the Cheesecake Factory. Though this place does serve ordinary dishes, it’s famous for… you guessed it – cheesecake. Choose from dozens of variations and enjoy the best view of Union Square from the outside balcony. Other good shopping choices in the area include nearby Maiden Lane on Morton St. and the Westfield Shopping Center on Market.

  • Union Square San Francisco

A short stroll away on the corner of Grant and Bush is the entrance gate to a totally different world, Chinatown. San Francisco is home to the oldest Chinatown in the US and walking through some areas of it really does feel like you’re in a different place. Chinatown is concentrated around two major streets: Grant and Stockton, along with the side streets in between. Grant Avenue is more tourist-oriented while Stockton Street is home to more locally used businesses. The best and most famous way to enter Chinatown is via the Grant Avenue Chinatown Gate.

Chinatown Gate San Francisco

As you walk up Grant Avenue, you are greeted by dozens of kitschy shops selling anything from Chinese firecrackers to giant ceramic vases. You’ll soon hit the cable car tracks of the California Street line and a red brick church – Old St. Mary’s Church. Head inside the church for a great photo exhibition of the area just after the devastating 1906 earthquake and fire that brought immense destruction (and reconstruction) to this part of town. If you come here at noon on a Tuesday, you’ll also be treated to a classical concert! Grant Avenue from this point looks just lovely, decorated with a Chinese touch all across.

Old St. Mary's Church

From Old St Mary’s Church, we went on a little detour, climbing California Street. Stop at the corner of Stockton St. and wait for a cable car to climb up or roll down the hill. This is a great photo spot with the skyscrapers below and the Bay Bridge making a slight appearance in the background.

Cable Car San Francisco

Further along California St. is Grace Cathedral which looks like a church straight out of Europe. This is one of the nicest spots in Nob Hill. If you really feel like getting a good view and further exploring this neighborhood, continue up to Ina Coolbrith Park on Taylor St. for one of the best downtown views. You might even have this place all to yourself.

  • Grace Cathedral San Francisco

Now back in Chinatown, it was time to explore Stockton St. Abundant with vegetable stalls, Dim Sum joints, and fish markets, this place has an authentic feel to it, in sharp contrast to souvenir shop lined Grant Avenue. Turn right on Clay St. and then either right or left on Waverly Place, a very small but beautiful street. On this tiny street, look above you and you’ll see magnificent Chinese pagodas. Waverly Place is home to numerous temples. At #109 is Norras Temple and at #125 is Tin How Temple, which we visited. Don’t let the modest staircase fool you, this active Tibetan temple is magnificent. Incense is continuously burned and traditional Chinese red ornaments light up this prayer chamber. Step outside onto the balcony and admire the tranquility of this place, at the heart of bustling Chinatown. Entrance is free but donations are highly appreciated, no photography is allowed.

Fortune Cookie Factory San FranciscoNow open up your smelling sense and walk up the tiny Ross Alley. You’ll soon smell something familiar (it’s not ‘weed’) and just towards the end, find the Golden Gate Fortune Cookie Factory. Step inside this crowded working factory that’s been making fortune cookies since the 1960s. Watch how cookies (and fortunes) are made and also buy a small bag if you want ($1). Also, be prepared to pay 50 cents for taking photos but it’s totally worth it. Just across the road is Delicious Dim Sum on Jackson St, very popular with the locals.

Take a right on Grant and a left on Washington St. and you’ll see across the street a beautiful Pagoda housing the East West Bank but better known as the Chinese American Telephone Exchange Building. Opened in 1909, this former busy telephone exchange was manned by operators who routed the calls by memorizing each subscriber’s destination, as Chinese homes did not have a number, due to traditional customs.

  • Ellision Enterprises San Francisco

Just across from you at 763 Washington St, head into Ellision Enterprises Corp. Don’t let the ambiguous name fool you, this traditional Chinese medicine shop is lined up with hundreds of different herbs for any ailment and excellent tea options. Pharmacists still use hand-held scales to serve customers – really cool to see and great if you’re in the market for some ginseng.


Back on the other side of the street was our last Chinatown stop, Portsmouth Square. This little square is extremely popular with the locals and you’ll see many congregate in small circles and watch as two battle it out in an intense game of Chinese checkers.

Portsmouth Square San Francisco

San Francisco’s Chinatown was by far the coolest one we’ve ever visited. There are so many spots to explore and it’s amazing what just a few city blocks in San Francisco can do, to completely change the atmosphere – a theme that would repeat itself on our city journey.

Chinatown San Francisco

It was time for a late lunch by now so we walked down to Columbus Avenue via Kearny Street towards Washington Square Park. Along the way, stop at the intersection with Pacific Avenue and Kearny Street, for a great view of new and old architecture in San Francisco. You’ll see the famous Transamerica Pyramid which was completed in 1972, in the backdrop of the Columbus Tower, completed in 1907.

Transamerica Pyramid San Francisco

Further along Columbus Avenue, you are now entering the area known as North Beach. This part of town is Little Italy and at just a few blocks away from Chinatown, really shows how diverse San Francisco is.

North Beach is home to many Italians and many Italians mean great food and European style cafes.

  • Mario's Bohemian Cigar Store Cafe

You’ll find dozens of good options in this part of town. We stopped for lunch at Mario’s Bohemian Cigar Store Cafe. This cafe has a simple and inexpensive yet delicious Italian menu and a great selection of Italian flavored soda. The staff is friendly, the food is great but the bathroom could use a makeover. We enjoyed the cannelloni and turkey focaccia with fine Washington Square views.


After a good lunch, we headed for a stroll in Washington Square Park. This is a very popular hangout spot and if you come in the morning, you’re bound to see Chinese seniors practicing their tai-chi. Saint Peter and Paul Church cannot be missed from the park area, and its two towers are a dominant feature in the local skyline. We had already done quite a bit of walking so relaxing in the park was a pretty good idea.

Washington Square Park San Francisco

Our next stop was the Coit Tower on Telegraph Hill and we made our way via the Filbert Steps on Filbert Street. The climb is compensated by great vistas which come into view as you head up to one of San Francisco’s most famous landmarks. The Coit Tower was built in 1933 and rises like a pin over Telegraph Hill. The view from Pioneer Park, where the tower resides, is amazing with the entire San Francisco Bay just below you, along with Alcatraz and the Golden Gate Bridge to the west. You can climb to the top of Coit Tower but since the queue was too long, we decided to just enjoy the view from the park.

  • Coit Tower San Francisco

You can head back down the same way you came but a better option is to take the Greenwich Steps down towards the opposite side. This steep staircase takes you through a lush urban forest and through some beautiful homes with enviable views.

Greenwich Steps Coit Tower

From here, we headed to the Embarcadero and caught the ‘F’ streetcar back to Market Street. For dinner, we decided to explore Japantown and went to Isobune Sushi at the Japantown Plaza. Japantown certainly lacks the architecture and vibe of Chinatown but there’s a great choice of excellent sushi restaurants around here. The plaza is really a small shopping center that’s worth visiting when the shops are open if you’re into crafts and Japanese fine paper. Isobune Sushi is not your average sushi joint. Guests sit around a river, where boats deliver the sushi that’s being prepared by the chefs in the ‘island’. Take what you want and pay according to the plate’s color. The sushi is simple and not the fanciest in town but this place certainly gets points for originality and the sushi is not bad at all. It’s also extremely reasonably priced and we had boatloads of sushi for only $45 including beer.

Isobune Sushi San Francisco

Any regrets?

  1. We really enjoyed Chinatown and wish we had more time to explore. There are a few good tea shops in Chinatown that we wanted to try.
  2. The view from Pioneer Park is really amazing. However, we would have loved to catch the unobstructed view from the top of the Coit Tower but the queues were simply too long.


  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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