5 Days In San Francisco

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

We’ll spend the first day in San Francisco exploring its flat downtown area, later ascending to Chinatown and checking out what’s happening on a few of its scenic hills.

Market Street

Close to the Union Square area, history lovers can begin the day with a quick stop at Lotta’s Fountain, located at the corner of Kearny and Market 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 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. This section of Market Street is also a prime shopping destination, highlighted by the Westfield San Francisco Centre.

Lotta’s Fountain san francisco
san francisco street car on market street
wells fargo bank sign - san francisco

At the corner of Market Street and Powell Street, check out the creative way in which cable cars are turned around when they reach the end of the line. This spot marks the beginning or the end of the Powell-Hyde and Powell-Mason lines. There’s a ticket booth nearby and it’s quite busy (yet orderly) with tourists queueing up to be the first ones to get on the cable car. You can technically hop on a cable car at any station along the route.

san francisco cable car turnabout station

Union Square

If you still haven’t had breakfast, head to Union Square and find a spot at Sears Fine Food on Powell St. just across from the Sir Francis Drake Hotel. Apart 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 notice that 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). 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 is Union Square, San Francisco’s upscale shopping area. 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 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 made up of two buildings, one for men and the other for women. If you’re visiting from outside the U.S., inquire about the visitors’ pass, which should provide a 10% discount at Macy’s.

Union Square san francisco
cable car near union square san francisco
hotel in Union Square san francisco

Be sure to also make your way to the Cheesecake Factory, located on the top floor. Though this place does serve ordinary dishes, it’s famous for… you guessed it – cheesecake. Choose from dozens of variations and enjoy a bird’s eye 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 back on Market Street.

View of San Francisco Union Square from Cheesecake Factory


A short stroll away on the corner of Grant and Bush is the iconic pagoda entrance to Chinatown. San Francisco is home to the oldest Chinatown in the US and walking through some areas of it does feel like you’re in a different country. Chinatown is concentrated around two major streets: Grant and Stockton, along with the side streets between them. 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.

San Francisco Pagoda Gate into chinatown
Shop sign in San Francisco chinatown

As you walk up Grant Avenue, you are faced with 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 marys church san francisco chinatown exterior
old st marys church san francisco chinatown interior

From Old St Mary’s Church, climb on California Street to the corner of Stockton for a photo-op detour. Wait at this spot 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.

taiwan flags in san francisco chinatown

This is also a convenient starting spot for exploring Stockton Street, abundant with vegetable stalls, dim sum restaurants, and fish markets. This is quite an authentic slice of Chinatown, unlike 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.

Street in San Francisco chinatown
pagoda in san francisco chinatown
taiwan flags in san francisco chinatown

Waverly Place is home to numerous temples. At #109 is Norras Temple and at #125 is Tin How Temple. Don’t let the modest staircase fool you, the latter is an active Tibetan temple. 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.

temple in san francisco chinatown

Now 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 to snack on later in the day.

Golden Gate Fortune Cookie Factory chinatown san francisco

Architecture enthusiasts can now head to check out the extravagant pagoda of the East-West Bank, 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.

Slightly down the road at 738 Washington St, step inside Ellision Enterprises Corp. Don’t let the ambiguous name fool you, this traditional Chinese medicine shop is lined 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.

Portsmouth Square san francisco chinatown - chinese checker game

For the last “official” stop on the Chinatown tour, cross the street, and explore Portsmouth Square. This little square is popular with locals, mostly seniors, and you’ll see many congregate in small circles and watch as two players battle it out in an intense game of Chinese checkers.

Ellision Enterprises Corp traditional chinese medicine - chinatown san francisco
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San Francisco’s Chinatown is worth exploring, even if you just stroll through. It’s amazing what just a few city blocks in San Francisco can do, completely changing the atmosphere. This is a theme that you’ll notice throughout the city’s distinctive neighborhoods.

Nob Hill

From our last stop in Chinatown – Portsmouth Square – walk up scenic Washington and enter the outskirts of Nob Hill, an affluent and picturesque neighborhood. As its name suggests, the area is built on a hill so getting up here does put your feet to work.

nob hill san francisco

Take a break from the climb at the San Francisco Cable Car Museum, located at the corner of Washington and Mason (free admission). At the very least, a convenient bathroom stop, if you’re either traveling with children or if you appreciate history and old technology, visiting the cable car museum is a must. Inside, you’ll learn about the history of this engineering marvel and also see the cables that run the entire system at work. In other words, this museum is not only a museum but also a critical function in the cable car infrastructure.

San Francisco Cable Car Museum
San Francisco Cable Car Museum - working cables

Next up, check out the European-looking Grace Cathedral. This is one of the nicest spots in Nob Hill, with the tranquil Huntington Park just across the street.

Grace Cathedral from Huntington Park - san francisco

A short stroll from Washington Park brings you to the tiny scenic lookout known as Ina Coolbrith Park. This spot offers some of the finest views of San Francisco and it’s a great spot for a picnic lunch or just a scenic break. This part of town has some seriously steep roads, making you wonder how the breaks on your car must be if you’re a neighborhood resident.

steep streets in nob hill san francisco
alcatraz island from nob hill san francisco

Little Italy

It’s time to head down to level ground in the direction of Washington Square Park. Along the way, stop at the intersection of Columbus Avenue with Stockton and Green St. for a great view of new and old San Francisco architecture. You’ll see the famous Transamerica Pyramid which was completed in 1972, in the backdrop of the Columbus Tower, completed in 1907.

Further down Columbus Avenue, you are now entering North Beach. This part of town is Little Italy and just a few blocks away from Chinatown, here’s another example of San Francisco’s diversity of neighborhoods. North Beach is home to many Italians and many Italians mean great food and European-style cafes.

little italy san francisco

You’ll find dozens of good casual dining options in this part of town. At Mario’s Bohemian Cigar Store Cafe, choose from a simple and inexpensive yet delicious Italian menu, along with a selection of Italian-flavored soda. The staff is friendly and the food is great. Try the cannelloni and turkey focaccia, with a side of fine Washington Square views.

Other solid nearby options include locals’-favorite Tony’s Pizza Napoletana, Golden Boy Pizza, Gino & Carlo, and the French cuisine at Cafe Jacqueline. Also worth mentioning are the fine focaccias at Liguria Bakery and the extremely-popular brunches at Mama’s On Washington Square (open until 2 pm on weekdays and 3 pm on weekends).

Tony's Pizza Napoletana little italy san francisco

After a good lunch, take a break at Washington Square Park. This is a 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, and its two towers are a dominant feature in the local skyline. It’s worth checking if the church is open and seeing its lavish interior with your own eyes.

Washington Square Park san francisco
Washington Square Park from coit tower san francisco
Saint Peter and Paul Church san francisco - exterior
Saint Peter and Paul Church san francisco - interior

Coit Tower

Well rested, it’s time to put the legs back to work. Head to Coit Tower on Telegraph Hill via the Filbert Steps. The climb is rewarded with great vistas in 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 is amazing with the entire San Francisco Bay just below you, along with Alcatraz and the Golden Gate Bridge to the west.

Coit Tower San Francisco
Alcatraz from Coit Tower parking - san francisco
golden gate bridge from Coit Tower parking - san francisco
telegraph hill parking - san francisco coit tower

If the queue isn’t too bad, it’s worth climbing to the top of Coit Tower (approx. $10). The views from here are even better and the breeze is great on a hot day. You might even catch a glimpse of birds riding the wind to hover in the air close to the tower.

View of San Francisco downtown from Coit Tower
View of Alcatraz from Coit Tower - San Francisco
san francisco bay from top of coit tower san francisco
ferry terminal and bay bridge from top of 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 waterfront. This steep staircase takes you through a lush urban forest and some beautiful homes with enviable views.

Greenwich Steps telegraph hill san francisco

Dinner in Japantown

Japantown is not an area we’ll devote much time to in this itinerary so it’s a good idea to check it out over dinner. It certainly lacks the architecture and vibe of Chinatown but there’s a great choice of excellent Japanese restaurants around here. We sampled the food at Isobune Sushi, located at the Japantown Plaza whose shops are certainly worth visiting 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 on 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.

Isobune Sushi on boats japantown san francisco