How to spend a weekend in San Francisco

Planning on a trip to the Golden City any time soon? Or are you just intrigued by what the Californian metropolis has to offer? Look no further than this jam-packed day-by-day guide. 

San Francisco’s Chinatown is unmissable, due to both its gargantuan size (it spans 24 square blocks and hosts one of the largest Chinese communities outside Asia), and the mouth-watering scents that snake up out of hectic basement kitchens. By American standards, this section of town is old. Very old in fact, having been established way back in 1848.

Owing to its size, there really is an endless list of places to eat so if you have a sudden craving for won-ton soup while out and about in San Fran, your stomach won’t be grumbling for long.

Stockton Street is the main thoroughfare for Chinese food shops, and “general stores”, while the streets that connect to it include most of the restaurants and cafes that heavily perfume the district.

For the nightcrawlers, Chinatown has dive-bars that could give the famed bars of New York a run for their money. LiPo Cocktail Lounge, a funky 1930s hole-in-the-wall decorated with lanterns and a known haunt of the late celebrity chef Anthony Bourdain, is one of them.

As a cocktail lounge, the place is known for its Mai Tai but the Chinese beers on tap are a must too. Also worth checking out is the Buddha Lounge, a darkly-lit affair where you can try some Chinese whiskies.

Sweet tooth? Round off the afternoon by traversing down to Insomnia Cookies located on the southern edge of Chinatown on Kearney Street, where you can tuck (or break) your teeth into a monster sized ice cream sandwich. If you’d rather keep things on the (slightly) healthier side, you can always pop into Matcha Cafe Maiko for either matcha tea or ice-cream.

A red-velvet cookie that you can nab at Insomnia Cookies

The Italian shopfronts on Columbus Avenue

Make a short detour north from Chinatown and you’ll find yourself suddenly in the streets of Italy—of the windswept San Franciscan variety, of course.

Columbus Avenue is the main thoroughfare of the area, and the warm fairy-lit pavement seating areas of family run trattorias, pizzerias and wine bars attract throngs of people in the evenings, so it’s worth booking a table in advance if you don’t want to be disappointed.

Given the fact that California is a wine producing state, and San Francisco’s proximity to the famous Napa Valley, it’s only fair that you don’t neglect to try the award-winning wines that Cali has to offer while wining and dining in Little Italy.

If you’re on the prowl for a quick bite to eat, pop into Molinari Delicatessen, a fifth generation Italian deli for some delectable salami and mozzarella sandwiches or head to the Liguria Bakery on Stockton Street for green onion, rosemary, mushroom and pizza focaccia, baked out of an oven more than a century old.

Saints Peter and Paul Church, above, is the spiritual hub of many locals 

If you’re looking for a moment of respite from the hustle and bustle, the quiet greenery of Washington Square is an inviting space to kick your feet up for a while. Directly across from the square sits the striking Saints Peter and Paul Church (rebuilt in 1924 after the Great Earthquake of 1906 destroyed its first 1884 incarnation) which has been remarked as being the “Italian Cathedral of the West”.

Fun fact: Marilyn Monroe and Joe DiMaggio returned for photographs on the steps of this church after their wedding in 1954, while a number of Hollywood films including parts of Sister Act 2 were filmed here. In recent years the church has become the spiritual home of the Chinese American Roman Catholic population, and it offers weekly masses in Cantonese alongside Italian and English.

Overlooking Little Italy and perched upon Telegraph Hill is the famous Coit Tower, an art deco masterpiece 64 metres tall which offers almost unparalleled views of the San Francisco Bay.

The Coit Tower overlooking Little Italy, with Alcatraz Island in the background 

Step inside and you’ll be greeted by a mural depicting San Franciscan workers of all industries, in a fresco that wraps around the entire ground floor lobby. While the murals are free to view, a non-resident adult ticket to go to the top of the tower costs ten dollars.

After admiring the views, be sure to round off your day with fresh gelato at one of the many ice cream parlours on Columbus Avenue. Delicioso.

San Francisco is consistently ranked as one of the most public transport friendly cities in the US, with 464 miles of bike lanes, as well as a well-connected cable car, metro and bus network. Unlike most of the rest of America, visitors don’t need to rent a car or endlessly order taxis to get around.

Go Bike It, located at the bottom of Telegraph Hill and just a short walk from Little Italy, offers day rates starting at $29 for adult bikes. Once you’re on your bike, head north down Mason Street towards Fisherman’s Wharf. This pedestrian-friendly area is home to Boudin Bakery Cafe where you can try their world-famous clam chowder soup served in a sourdough bread bowl.

A delicious clam chowder bread bowl 

Pier 39, a water-front complex featuring restaurants, gift shops, and an aquarium is also worth checking out though it has to be said it truly comes alive at night when you’ll also be able to witness live acts and performances at the head of the pier.

After taking in the sights of Fisherman’s Wharf, cycle west on Jefferson Street and follow the cycle trail past Ghirardelli (a famous chocolatier) and along the waterfront until you reach the remarkable Palace of the Fine Arts.

An oasis of calm in the madness, built specifically for the 1915 Panama-Pacific Exposition, the main spectacle is a 49 metre Ancient Romanesque building with an open rotunda ceiling in the middle of a lagoon.

The Palace of the Fine Arts lagoon and its spectacular dome

From the Palace, head west again and cycle onto the Golden Gate Beach, where you’ll be greeted with the looming, iconic beauty of the Golden Gate Bridge. If you’re in need of a pause, this windswept beach is a cute spot for a picnic or for watching surfers as they crash onto towering waves.

The Golden Gate Bridge stretches across the Bay for nearly two miles and you can cycle its entire length and head north to the vineyards and rugged beauty of the Marin Headlands—be prepared for the gusty winds though!

On your return to San Francisco head south-west along the Presidio Park for a breezy downhill ride along the waterfront that will eventually take you to Ocean Beach, where you can gaze in awe at the immensity of the Pacific Ocean. It’s no doubt a sight that will make the bike ride worth the earlier uphill struggle.

The beautiful serenity of the Japanese Tea Garden makes it a must-visit 

At three miles long, Golden Gate Park is 20 per cent bigger than New York’s Central Park, and it isn’t an exaggeration to say you could spend the best part of a day here. It features a stunning Botanical Garden ($10 entry), and the Japanese Tea Garden, the oldest garden of its kind in the country.

In the middle of the Park you can find Strawberry Hill, where a Chinese peace pagoda sits in its unrefined beauty. In the north-eastern corner stands the DeYoung Museum, a fine arts museum where you can indulge in a huge selection of American art.

If you’re in the mood for some shopping, take a wander down Haight Street, which is immediately east of the Park. Featuring a plethora of upscale bars, and boutique hipster clothes shops, it’s well worth a visit.

After your shopping spree, head east down Haight Street until you reach Steiner Street, walk north a couple of blocks and you’ll reach the ubiquitous Painted Ladies, a row of colourfully painted large Victorian and Edwardian houses lining Alamo Square, a petite park with beautiful views of the city. Rest here and take pictures to show off on your Instagram feed (or not).

Alamo Square offers both a view of the Painted Ladies and a breathtaking sight of the San Francisco skyline

Looking for a spot to eat? A short walk away on Hayes Street you can find Papito, a small and inviting Mexican restaurant and bar serving luscious burritos for an affordable price.

If you’re not tired from cycling earlier, get your skates on at the Church of 8 Wheels which is a roller rink housed in an otherwise unassuming church. If you can’t visit on the weekend, bear in mind that it is closed on Mondays, Wednesdays and Thursdays.

Downtown San Francisco is teeming with museums and art galleries that are well worth a visit. In the Yerba district you can come across three museums alone: The Contemporary Jewish Museum, Museum of the African Diaspora, and the San Francisco Museum of Modern Art.

In the Civic Centre district, you can find The Asian Arts Museum, which houses some of the most comprehensive Asian art collections in the world, while the city’s theatre district is a short walk away.

This is the city of Harvey Milk, the famous gay rights activist and politician who was killed for his beliefs, and you can learn more about San Francisco’s history of Queer activism at the GLBT Historical Society Museum in the Castro district.

You can’t miss the bright rainbow flags and lights of the Castro district, the home of San Francisco’s sizeable queer community.

San Francisco is known for being a queer-friendly city, with its globally renowned Pride procession normally attracting nearly two million attendess on each given year, and Castro Street is its hub.

If you’re looking to line your stomach before a night out in Castro you have to give Orphan Andy’s a go. A delightful neon-lit old-school diner with a mouth-watering menu fit for champions, it’s open 24/7. From stuffed French Toast to Banana hotcakes and splendid bagels to filling steaks and burgers, the choice on offer is dazzling.

The sparkly interior of Orphan Andy's 

Your night out can include watching a film at the historic Castro Theatre, or bar-hopping of course.

If your knees can still carry you, an evening sunset hike up to nearby Twin Peaks, two 282 metre hills, is a perfect way to round off your visit to the Golden City. If you can’t manage the hike, don’t worry, as you can drive up to the top too.

A nighttime view atop Twin Peaks

Twin Peaks provides probably the best vantage point in the entire city so prepare to gasp at the mesmerising glittering cityscape below you when you make it to the top. The sight just might make you feel San Francisco is yours for the night.

Read more: How celibacy became cool

Read more: Exploring Cape Town's revival

To claim your exclusive access code to our discounted travel club and to keep up with the top stories from Reader's Digest by subscribing to our weekly newsletter