5 Days in San Francisco – a 5 Day San Francisco Itinerary

5 Days in San Francisco – How to Make the Most of the City

In 5 Days in San Francisco, with careful planning, you can have a full experience of the city. In this 5 day San Francisco itinerary, you’ll be able to make the very most of your stay. It covers the principal sights and the world-class museums. It also gives us a taste of Northern California’s natural splendor.

We’ll also make time for dining, neighborhood walks and getting the flavor of local life. This city is a fantastic place for an urban holiday – even better, it makes the ideal destination for a gorgeous Pacific Coast Highway road trip.

5 Days in San Francisco, Day 1 – Get Oriented with a Tuk Tuk Tour. Then, Union Square and Cocktails in the Tonga Room

To really feel like you have experienced a city and you know it, you need to get an overview. Speeding from landmark to landmark via UBER or metro, you miss how one area relates to another. Also, you miss all of the texture in between. If you have 5 days in San Francisco, you won’t be able to see the whole city on foot.

We had a fantastic time making a huge loop of all the principal sites in a comfortable tuk-tuk on this excellent San Francisco tuk tuk tour. Our guide, Bailey, knew plenty of entertaining and informative stories to help us get to know the city. We stopped for photos and a break along the way. I have never had a better introduction to any city I have visited. Moreover, this was not my first visit to San Francisco. It was, however, the first time I saw nearly all of it all at once in the space of an afternoon.

This was the perfect start to a 5 day San Francisco itinerary – a fun and thorough orientation. After this complete overview, we were able to give our favorite sites the time they deserve in the coming days.

Union Square, San Francisco

We finished our tour in Union Square. This is the commercial center of downtown. The large open square has a couple of cafes as well as plenty of seating and tables. San Franciscans meet here to eat their lunch, as visitors enjoy a coffee and taking photos of the surrounding skyscrapers. Even if you do not care for shopping – several world-class shops like Tiffany and Gucci are around the square – you may enjoy the cosmopolitan buzz.

Cocktail Time

Have your first San Francisco cocktail in a unique lounge, part of the nightlife of San Francisco for decades. The Tonga Room and Hurricane Bar, in the legendary Fairmont Hotel, offers plenty of photogenic, tropical decadence. Enjoy a menu of bites inspired by the Pacific Rim, and elaborate cocktails just as San Franciscans have been doing since 1945. Oh, also – they call it the Hurricane Room because they actually stage periodic tropical rainstorms with thunder and lightning.

A 5 day San Francisco itinerary, day 2 – Art and Culture Downtown: SFMOMA, the Jewish Museum. More Art and Culture: Castro, The Mission

Today, we’ll see two of San Francisco’s finest museums – one a powerhouse of contemporary culture, the other a more intimate, manageable experience. By starting out early at the SFMOMA, we can give it a good two or three hours to see the highlights.

As in any great city, its true heart is in the neighborhoods. The Mission and the Castro are two of the best neighborhoods in San Francisco for getting in touch with the culture and pace of the city.

Minamoto Kitchoan – Japanese Patisserie

Market Street is one of the main streets of downtown San Francisco. The main transportation lines – the BART, MUNI, street cars, and several busses run along Market Street.

First, near the Montgomery Street Station of the BART, on Market Street, is a famous Japanese patisserie/confisserie. The displays and the confections themselves are so exquisite it looks like a jewelry store. Try a delicate mochi scented with cherry blossoms or any other of the ethereal confections, many of them seasonal. Since we’re having an art day, it makes sense to start with an edible work of art.

SFMoMA

The San Francisco Museum of Modern Art is spectacular, definitely one of the highlights of 5 days in San Francisco. After tripling its size in a stellar expansion by the architectural firm Snohetta, the SFMOMA is now among the largest museums of modern and contemporary art in the United States. The collections include familiar highlights of early 20th century art – Kandinsky, Tanguy, Khalo, Magritte, etc. But most compelling are the vast collections of later 20th and even 21st-century works. These span early Lichtenstein, Thiebault, Still, Richter, Kiefer, and many others. Expert to see some monumental paintings, some of tremendous scale, in amazing spaces.

Take a Break

For hectic downtown, places for a snack or a coffee rarely come more pleasant or affordable than the museum’s own places. Moreover, the SFMOMA shop is an excellent place for gifts and books related both to contemporary art and culture and to San Francisco itself.

The Contemporary Jewish Museum

Architect Daniel Libeskind’s vision for the Contemporary Jewish Museum, incorporating a historic power station of 1881, is reason enough to visit. The building is wonderful, from the inside and from without. Exhibitions inspired by Jewish culture and the Jewish presence touch on universal aspects of life. Most recently, the central exhibition relates to Levi Strauss, the inventor of the iconic American garment that has defined decades of sartorial culture and identity. The Contemporary Jewish Museum of San Francisco is very close to the SFMOMA

After visiting these famous centers of contemporary culture, we’ll feel the cultural pulse of the city in a more intimate context, by visiting two of the city’s best-known neighborhoods – Castro and the Mission. Getting there is part of the experience.

Taking the Streetcar F from Market Street

The San Francisco MUNI system includes some lines serviced by gorgeous streetcars from the 1930s and ’40s in excellent condition. The F line runs from Fisherman’s Wharf to the Castro, via Market Street. You can’t get lost – we’re going to the last stop – 17th Street and Castro.

The Castro

This is ground zero for San Francisco’s LBTG/LBTGQIA community. San Francisco has been proudly progressive about sexuality, identity, and alternative lifestyle choices for decades. This means it’s an important center for the worldwide community, flag flying high. The Castro is the heart of Gay San Francisco and is one of the most vibrant neighborhoods of the city.

The Castro is one of San Francisco’s most lively and interesting neighborhoods for the visitor as well as for locals. We’ll find excellent shops and cafes, street fashion and lifestyle.

Stop by the Castro Theater to see their schedule. This classic grand movie house of 1922 shows first-run features, classics, and has famous sing-alongs to musical films.

After visiting the main commercial streets, we enjoyed walking through the residential neighborhoods with their classic examples of San Francisco’s famous Victorian architecture. Pass by Le Maison Bleue – once a famous commune and the inspiration for the 1972 Maxime le Forrestier song (it’s on 18th street between Sanchez and Church). Then continue the French vibe with an impeccable croissant and a cafe au lait at charming Le Marais, on the corner of 18th and Sanchez.

We’re now near Mission Dolores Park.

The Mission

One of the most famous neighborhoods of San Francisco, Mission is a fascinating mix of its local Spanish-speaking population, street art, and creative communities. It takes its name from the actual Mission – the historic Mission Dolores.

Mission Dolores

Originally, and still, the Mission of St. Francis of Assisi, this historic Mission of 1776 is almost always called Mission Dolores, for a creek that was once nearby. This is one of 21 historic Missions of California. This beautiful building is the oldest intact building in all of San Francisco. Come here to see first hand an example of Mission style architecture, which you will see emulated in homes and mansions throughout California. In the cemetery of the Mission rest original Californians of the Ohlone and Miwok, as well as early settlers.

Mission Dolores Park

From this beautiful park on its hilly slope, we’ll enjoy great views of the city. It’s also perfect for people watching. We can like the locals and grab an ice cream at the nearby Bi-Rite.

Creativity Explored

For an inspiring start to our art-forward exploration of the Mission, we can visit Creativity Explored. This community of artists with developmental disabilities create beautiful and moving works in an airy studio space. A gallery and a store are in front.

Street Art

The mission is world-famous for street Art. We’ll see it all over the place throughout this large and diverse neighborhood. But here are a few addresses that are particularly rewarding:

Clarion Alley

Parallel to 17th Street between Valencia and Mission, Clarion Alley is the center of the CAMP (Clarion Alley Mural Project), started in 1992. Here we’ll find hundreds of murals exploring political themes, community soul, and social consciousness.

The Women’s Building

On 18th Street we’ll find the Women’s Building This community center , which opened in 1971, houses and fosters a host of women’s organizations, workshops, services, and celebrations. The 1994 mural, which covers the entire facade, is the collaborative work of several local female artists. It celebrates the contributions of women throughout time, both mythic and historic.

Balmy Alley

At the other end of the neighborhood, off of 24th street which is one of the main streets of Mission is another famous alley of murals – Balmy Alley. The original works here focused on the female experience and was started by the all-female collective Mujeres Muralistas in 1972. Subsequent waves of works focused on indigenous Central American cultures, and more lately the challenges that face the community, including police harassment, narcotics, and gentrification.

Precita Eyes

Those with a strong interest in street art and the history and present of the street art of the Mission district in particular can check in at Precita Eyes. Here, at this non-profit arts organization dedicated to art and community, we found books, information, and guided tours

5 Days in San Francisco, Day 3 – Must-See Highlights

Just because we’re interested in high art and street culture doesn’t mean we should overlook the obvious. This the the all out fun day – full of classic “tourist” attractions of San Francisco. These are essential experiences for a complete 5 day San Francisco itinerary. Each is emblematic of the city.

Most of our activities will be at the waterfront. We will be covering much of the north coast of San Francisco.

The Ferry Building

The old ferry terminal had a complete renovation and reopened in 2003. Now, this beautiful and historic space has the best of California’s culinary scene, from artisanal bakers like Acme, Fromageries like Cowgirl Creamery, and inventive ice cream like Humphrey Slocombe.

From here, we can either board the street car F, but this time going in the direction of Fisherman’s Wharf, or we can walk. Keep in mind we will be doing a lot of walking today, though.

The Cable Car – Essential SF

We’ll start our day at Powell and Market Street to take the cable car – the Powell/Hyde line – over to the north side of the city.

The cable car was invented in San Francisco to scale the incredible hills the city is famous for. Cable cars were declared a San Francisco landmark in 1964.

Totally worth the $8.00 fare and the long wait in line (30 minutes is not at all unusual), the cable car is an icon, one of the best things to do in 5 days in San Francisco. It’s also more thrilling than you expect. The views are fantastic, the sounds cinematic, the engineering impressive. You really feel the power as they are pulled up by the cables running under the street. In order to have the best experience, ride standing up. But be careful, and don’t lean out.

Pier 39

A couple of blocks to the east is the most famous of San Francisco’s piers. To be sure its the most touristy. But the stars of the wharf make it worthwhile – this is home to many many Sea Lions, who find both safety from predators and plenty of delicious fish.

Pier 39 is also where our bay cruise sets off.

Bay Cruise

One of the best things to do in a 5 day San Francisco itinerary is to experience the city from the Bay. In order to do this, we took the Blue and Gold fleet’s one-hour Bay Cruise Adventure. This took us underneath the Golden Gate Bridge and round Alcatraz Island. Besides the excellent views and photo opportunities, there was informative narration, so we got a thorough overview of the history of the city and the specific sites we saw en route.

Fisherman’s Wharf

Any 5 day San Francisco itinerary will have to include Fisherman’s Wharf. Walking back towards Hyde street and passing Pier 39 brings us here. Even though this is a admittedly a very touristy strip along the bay, it has a certain retro charm, sort of ’70’s mood. Take a snapshot of the famous sign that looks like the steering wheel of a ship. Also, stalls sell Dungeness crab and other local fresh seafood specialties on ice – more fine photos. For a sit-down meal, many people enjoy the classic restaurants like Cioppinos and Aliotos.

From here, we will walk a couple of blocks to the corner of Hyde and Beach, just above the turning platform of the cable car.

Irish Coffee at the Buena Vista

On a 5 day San Francisco itinerary, it’s fun to visit a famous San Francisco institution like the Buena Vista. This classic bar opened in 1916, and is a great place to have a drink at the bar. The drink of choice, of course, is Irish Coffee, because the Buena Vista is the first place in the United States to serve it. The owner developed it with the help of a travel writer in the 1950s, modeling it on the coffee served at the Shannon airport. You sip the strong, hot and boozy coffee through a thick head of whipped cream.

Close by, just past the landmark Fontana apartment buildings, at North Point Street and Van Ness, we can catch the MUNI bus 28.

The Palace of Fine Arts

We’ll ask the driver where to get off for the Palace of Fine Arts. Here is one of the surprises of our 5 days in San Francisco. Around a pond filled with swans and other serene water birds is a series of monumental structures that look like the setting of a dream. The Beaux-Arts fantasy of a structure calls to mind monumental ancient ruins. The original Palace of Fine Arts was designed by Bernard Maybeck for the Panama Pacific Exhibition of 1915. Then, years later, citizens of San Francisco saved the temporary structure from destruction, and it was re-built from more permanent materials. This is one of the most romantic sights of San Francisco, indeed the world. The many bridal couples who crowd here for their photographs confirm it.

The same bus continues to the Golden Gate Bridge.

The Golden Gate Bridge – a Highlight of a 5 Day San Francisco Itinerary

5 days in San Francisco could not be complete without walking across the Golden Gate Bridge. This icon, a wonder of engineering and beauty, spans the strait between San Francisco and the Marin headlands. It marks the passage from the open Pacific Ocean to the San Francisco Bay. This was the “Golden Gate,” and it was in part called this because of the Golden Horn in Istanbul. Just as the Golden Horn was the gateway between east and west, so the Golden Gate was the opening to trade with the far east.

The Golden Gate Bridge was opened in 1937. The length of 1.7 miles / 2.7 kilometers made it the longest suspension bridge in the world when it opened. Even today, it remains among the world’s longest. It’s a magnificent sight. The color, made for the bridge, is called International Orange and it glows with beauty. The stylish bridge is crafted with the Art Deco details of its era.

It’s well worth the long walk across for the stunning view of the bay. But first, we can read about the history of the bridge from the informative outdoor displays, which will make our walk more fun. As we walk, we’ll get an up close experience of the monumentality of this world-famous landmark.

After walking across the bridge, we can stop at the visitors’ center for general San Francisco information. There’s also an excellent souvenir shop (not an oxymoron – they had tasteful and pretty things). Additionally, there’s a coffee place with, of course, a fantastic view.

We can now board the bus #28 going in the opposite direction- back to North Point Street and Van Ness – from the very same bus stop where we got off.

Ghirardelli Square and Cheese and Wine at the Cheese School

Another favorite landmark and on many a 5 day San Francisco itinerary, the Ghirardelli Chocolate Factory on the bay of San Francisco is now a restored industrial building housing many businesses. It looks like – and is – another tourist spot. But it is also a surprisingly excellent location for a delicious tasting meal.

At The Cheese School, we enjoyed fantastic views of the bay through the wall of glass, while sampling superb cheeses. Each board came with a careful selection of quality local cheeses and accompaniments such as raisins steeped in desert wine and crisp nuts. Wines by the glass were delicious. This really is a school – you can even come for seminars about cheesemaking and inevntive cheese pairings with wine or chocolate, for example.

If you’re still hungry, you can visit the Ghirardelli shop for a famous hot fudge sunday.

Day 4 – Japantown, Chinatown, North Beach, Coit Tower, Seafood at Pier 23, the Exploratorium

The fourth day of our tour brings us to the Western Addition for a stop in Japantown, then back into the popular tourist area. But this time the emphasis is on culture, social history, and lifestyle. Plus, we’ll visit an interactive museum that will make you feel the thrill of discovery, like being a child again.

San Francisco’s Japantown – Nihonmachi

Today, our 5 day San Francisco itinerary starts with total serenity. San Francisco’s Japantown – Nihonmachi as it is called in Japanese – is distinctive. This compact, spotless, and supremely peaceful district is the largest Japantown in the US. Japantown has a strong identity, organized around the elegant Japan Center of 1968. Its two buildings are separated by a plaza where we will find the elaborate five-tiered, 30 meter (100 foot) Peace Pagoda. We can shop for fine traditional products, visit the exquisite supermarkets, and join the locals at Benkyodo on the corner of Buchanan and Sutter streets for delicate mochi.

Learning about the Japanese-American Experience

Walking around the neighborhood, you’ll see plaques dedicated to the Japanese-American experience. Learning about the peoples who have made San Francisco this fascinating place is an important part of what we can experience in 5 days in San Francisco. Because of this, it’s worth taking time to read them, even though they are difficult. This is because they inform the reader about the internment camps where Japanese Americans were relocated to during the second world war. This is a shameful chapter in the history of the United States, from which hopefully much can be learned.

The MUNI bus #38 on Geary will bring us back downtown.

Chinatown

Another essential in a 5 day San Francisco itinerary, this is just one of several Chinese neighborhoods in the Bay Area. But the central downtown Chinatown is the most photogenic of all. In sharp contrast to Japantown, Chinatown is cluttered, not clean, very chaotic, and loud. It’s also quite fun. The ornate Chinatown gate opens onto Chinatown’s main drag – Grant Avenue. This is prime cheap souvenir hunting ground, with a few more elegant stores offering traditional Chinese clothing and gifts. Most locals eat Chinese food elsewhere. But there are dim sum parlors, restaurants, and bakeries for a snack. Our favorite snack of all was a sack of fresh, crisp fortune cookies (a Chinese-American invention) from the Golden Gate Fortune Cookie Factory in Ross Alley.

As we continue along Grant Avenue, we eventually come to Jack Kerouac Alley on our right, where the scene changes abruptly.

North Beach – The Birth of the Cool

One of the best things about spending 5 days in San Francisco is experiencing such radically different moods and characters from neighborhood to neighborhood. In San Francisco, each area has its own distinctive identity and history. Even though North Beach is directly next to Chinatown, it could not be more different.

North Beach is where the Beat Generation and Italian Culture mingled over strong cups of espresso. Walking through Jack Kerouac Alley, lined with quotes in the pavement and murals on the walls, we come to the corner of Columbus Avenue. Cafe Vesuvio is on our right, and the City Lights Bookstore is on our left. Founded by the poet Lawrence Ferlinghetti and Peter Martin in 1953, this is the birthplace of Beat Poetry. Then, two years later, they founded City Lights publishing. It remains a bastion of counter-cultural literature and thought and is an excellent bookstore experience.

If we turn left on Columbus Avenue, we’ll pass by Italian restaurants and espresso bars. North Beach has historically been an Italian American neighborhood, and it still has this flavor today. A perfect example is Molinari Delicatessen. It’s beautifully stocked and the best bet for a picnic lunch. So we can pick up one of their fabulous sandwiches and a San Pellegrino for a picnic in Washington Square, the park in front of Saints Peter and Paul.

One of the most famous Italian Americans to come out of North Beach was Joe DiMaggio of the New York Yankees. He also had a famous wife for a while – Marilyn Monroe. The famous couple took their wedding photos on the steps of this church overlooking the park. But they married at City Hall, because this is a Catholic church and they both were divorced. Washington Square is lively with people and dogs and makes a pleasant interlude.

Coit Tower

From Washington Square, it’s a short but extremely steep walk up to Coit Tower. This Art Deco style tower was built with a bequest from San Franciscan Lillie Hitchcock Coit. The tower is on a hilltop in Pioneer Park and rises 64 meters (210 feet) to offer sweeping panoramic views. Even if you’re not interested in going up in the tower – there is both a fee and a line for the elevator – it’s worth coming up here. There are also great views from the surrounding park, and the tower is lovely. The murals on the ground floor of the tower are prime examples of Social Realism.

The Parrots of Telegraph Hill

This is the Telegraph Hill neighborhood, and it has some exotic and elusive residents. Escape domesticated parrots have bred. Telegraph Hill proved a hospitable ecosystem, and now this flock of wild parrots numbers as many as 500. It’s worth keeping an eye out for these lovely birds. They are bright green with red heads and are hard to miss.

The Exploratorium

This hands-on museum of science, psychology, and perception is wonderful at any age. The regular hours are open for everyone. But there are also special evening hours – the Exploratorium After Dark – on Thursdays from 6:00 pm to 10:00 pm. The Thursday evening session, with events, music, and guest speakers, is only open to visitors 18 and over.

Seafood by the Pier

Pier 23 is a classic old-style San Francisco spot – on the pier of the same name – for classic old-style San Francisco seafood dishes. On the menu are clam chowder, shrimp and crab Louie, Dungeness crab in the shell, and superb fish and chips. They also serve hamburgers, and a good selection of beers and wines.

5 Days in San Francisco, Day 5 – The Palace of the Legion of Honor, Golden Gate Park, The California Sciences Center, the de Young Museum, Tea in the Japanese Garden, Haight-Ashbury,

We’ve hit many of the highlights of the center in our 5 days in San Francisco. So today, we can head for the open spaces and beautiful sights of western San Francisco. Our day will include museums, Golden Gate Park, and the Japanese Tea Garden, as well as one of San Francisco’s most famous neighborhoods.

The California Palace of the Legion of Honor

The Legion of Honor is a Museum of Fine Arts in Lincoln Park, a dramatic setting overlooking the Golden Gate Bridge and the Pacific Ocean. The museum is an exact replica of the French Pavillion of the Panama Pacific Exhibition of 1915 (the same exhibition that gave the city the Palace of Fine Arts). The French Pavillion, in turn, was a replica in 3/4 scale of the Palais de la Legion d’Honeur.

The collection here spans 6,000 years of Ancient and European art. The collection is particularly strong in European art of the 16th through 20th centuries, including masterworks by Titian, El Greco, Rembrandt, Gainsborogh, van Gogh, Monet, and Renoir. Additionally, there’s a grand gallery of sculptures by Rodin. There are also porcelains and other objects, reconstructed rooms of historic design eras, and books and graphic arts. Before leaving, we stopped in the museum’s cafe. With its outdoor tables on a patio under the trees, it has a Parisian charm.

Hang on to your admission Ticket; it will also cover admission the same day to the de Young Museum later on.

Golden Gate Park

This park of over 1,000 acres stretching from the Pacific Ocean to the heart of San Francisco offers a great variety of experiences.

The Japanese Tea Garden

This lovely Japanese Garden is complete with pagodas, a tea pavillion, a koi pond, a zen garden, and an arched drum bridge. Like the Palace of Fine Arts, the Japanese Tea Garden was originally conceived for a fair. In this case, it was a “Japanese Village” for an international exhibition in 1894. The project was expanded and made permanent by the landscape architect Makoto Hagiwara, who devoted his life and his personal fortune to the project.

Wonderful for wandering and contemplation, the Japanese Tea Garden also does serve tea, along with Japanese delicacies, in an ideally tranquil setting by a reflective pool.

The de Young Museum

Very close to the Japanese Garden, this museum’s collections comprise Oceanic art, African art, and art of the Americas. Additionally, they exhibit fascinating costume and textile Arts and graphic arts. The de Young museum also holds dynamic contemporary and thematic exhibitions of broad impact and interest. Tickets from your same-day admission to the Palace of the Leion of Honor will also grant you entrance to the Young. Special exhibitions are often charged separately.

The California Academy of Sciences

Across from the de Young Museum, this dynamic building is in itself a worthy destination. A study in sustainability, this is the “greenest” museum building in the world. Its architect, Renzo Piano, planned to “lift up piece of the park and place a building beneath.” explaining its beautiful integration with its surroundings.

The California Academy of Sciences comprises a planetarium, aquarium, a natural history museum, and even a rain forest. This is an education forward experience. We left feeling closer to our beautiful planet. We also gained an increased dedication to the environment and all our fellow living creatures. Truly an inspirational experience.

Haight Ashbury

Our 5 day San Francisco itinerary is nearly complete. We’ll finish with one of the best-known neighborhoods in all San Francisco worldwide – Haight Ashbury. Otherwise called the Haight, it’s usually known by its most famous intersection – Haight and Ashbury. The reason people all over the world know Haight Ashbury is that San Francisco became the epicenter of counter-culture during the Summer of Love, 1967. As many as 100,000 people converged here in Haight Ashbury, espousing counter-cultural ideals and rejecting war, materialism and conformist ideology and lifestyle.

Of course, the Haight has moved on with the times, and is now a prime commercial area for contemporary design boutiques, vintage clothing shops, and record stores. Still, there is a degree of nostalgia, and the hippie aesthetic lives on.

Using a San Francisco CityPass to make the most of a 5 day San Francisco Itinerary

We saved some money and a lot of trouble by getting a CityPass, there are a couple of choices – you can read about them here. Our CityPass included a 3-day MUNI passport covering buses, street cars, MUNI, and cable cars – so we could ride the cable cars as much as we liked. If you plan on seeing even more in your 5 days in San Francisco, you can get additional MUNI passports. They are available for one, three, and seven days. More information here.