How to Design Your 49 Mile Drive Trip in San Francisco

Have you heard of the scenic 49 Mile Scenic Drive?

The original scenic road tour highlight was created by the San Francisco Down Town Association in 1938 to showcase the city’s major attractions during the 1939 Golden Gate International Exposition. While the route was modified several times through the years, the loop around San Francisco remained. To me, it’s the best way to explore the city’s downtown area and have a taste of all the historic sites, landmarks, and natural beauty.


The 49 Mile Drive trivia

First of all, why “49 Mile”? In fact, the number “49” is not the length of the drive, nor a numbered highway; it represents the coverage of the size of San Francisco downtown, which is 49 square miles.

The route is marked by blue and white signs with a seagull featured on it. The sign was the winner of a design competition held by the Association back in 1955. Even if you don’t intend to, you might sometimes find yourself on a scenic drive when you are traveling in the city.

The signs themselves are part of the history of the scenic drive, and the signs are just too cute that they often get stolen! It takes time to replace the signs, so, while I don’t say you can truly rely on them to point you in the right direction on the drive, don’t forget to take a picture of it when you see them on the road.

How to Plan Your 49 Mile Drive

A detailed, free, and printable map of the route is available on the 49 Mile Drive website, which includes full details on every sport along the route. The list covers 37 spots and it might take a few days to complete if you stop by every one of them (For example, Alcatraz is an island in the harbor and it requires several hours to hop on a ferry and explore the island).

The quickest way to complete the route takes about 4 hours of driving to cover the entire route (just stopping at each spot for about a minute); It is also possible to complete the route in a day if you stop for about 10-15 minutes for some photo-taking, and take about an hour for lunch.

I would, however, suggest spending about 3 days covering the key locations and re-visit some of your favorite spots if you have more time. Just visit these places at your own pace and pick up where you left off the next day. The route is a loop, and so even if the spots are numbered, you may kick-start your scenic drive at any point and you would end up at the same spot – if you follow exactly the entire route.

I guess my point is that Mile Drive offers a good guiding reference for you to have good coverage of the major attractions (as well as places and Instagram-worthy spots that you may not be aware of had you just explored the city on foot or by public transportation) in San Francisco Down Town – how and when and where is completely flexible and up to you.

Besides, tackling the traffic, parking spaces, the one-way streets, and the slopes in the city could be confusing and frustrating to holiday drivers – you don’t want to waste your precious time navigating these streets just because you are sticky to the map. Be smart and make good judgments on the road.

For several spots, it would be much easier to simply park your car in one spot and explore a couple of places on foot. Whether you decide to follow the route strictly or not, the most important thing is that you get acquainted and enjoy your time in San Francisco. All in all, it’s a nicely designed “marketing” plan for tourists that has been kept for decades.


Here are some of my favorite spots on 49 Mile Drive, maybe, some of these places are new to you!

#2 Ferry Building and #3 Embarcadero

This is marked as the beginning and the end of the drive. The Embarcadero is the eastern waterfront and roadway of the Port of San Francisco, the Central Embarcadero Piers Historic District features a lot of Ferry Buildings along the city’s miles-long embarkment. It connects all the way to the Fishermans’ wharf in the north. If you start your day at this spot (like I do) – there are, in fact, some nice restaurants or cafes with windows of the ocean where you can enjoy a traditional America-style breakfast before your “big” adventure.

The current Ferry Building is a historic rehabilitation in 2003. Facilitated by Mayor Brown Jr., and the San Francisco Port Commission. The building is a multi-function complex at the city’s waterfront that features a few great restaurants, shops, and a farmer’s market.

The front of the building offers a great and unobstructed view of the Oakland Bay Bridge that connects to Oakland, and this is also where ferries will take you to Treasure Island.

San Francisco’s historic streetcarMuni, intersects at the Ferry Terminal station in front of the building. The streetcar is a good way to get around the city, as well as to the Castro District – a hip and trendy neighborhood with a lot of great restaurants and entertainment.

49 Mile Drive - Ferry Building

#4 California Street with Cable Cars and #6 Cable Cars at Powell

The cable car runs in Downtown San Francisco and it has been one of the most popular and recognizable attractions. It is the world’s last manually operated cable car system. Don’t be surprised when you see a long queue on California Street waiting to get on the cable car. There are three cable car lines: one starts at California Street and runs up the steep hills of the Financial District, and two starts at Powell and Market and continues to the Fisherman’s Wharf area. While passengers might be standing on the side of the car and holding on to the poles, the busy streets and steep hills might make your cable car experience an exciting ride.

49 Mile Drive - Cable Cars 1

#7 Painted Ladies

The Painted Ladies (720 Steiner Street) is a row of remarkable Victorian and Edwardian houses with the dramatic San Francisco skyline in the background. The houses were repainted in the 1960s with different colors that embellish or enhance their architectural details.

They have been called “Painted Ladies” since 1978, coined by writers Elizabeth Pomada and Michael Larsen in their book Painted Ladies – San Francisco’s Resplendent Victorians. The term is actually a general term that describes a row of the houses of the Victorian and Edwardian genres in three or more colors; Painted Ladies could be found in other cities like St Louis, Cincinnati, Baltimore, and more. Anyway, it is a great spot to take photos of historic houses with the city’s skyline in the background. For a full Hollywood experience, join a San Francisco Movie Sights City Tour.


#8 Union Square and Steep Hill & Chinatown

There are actually quite a lot of “Union Squares” in the world yet they are not as busy as the one in San Francisco. The public plaza is the central shopping district surrounded by shopping malls, restaurants, hotels, theatres, and entertainment in the busy streets of Powell, Geary, Post, and Stockton Streets. It’s filled with festival cheers during holidays like Christmas and New Year!

49 Mile Drive, Union Square, San Francisco

PC160169If you have more time (and if you can find a parking space, take a stroll a little further to the Moscone Center, SFMOMA (San Francisco Museum of Modern Art), and Contemporary Jewish Museum. Many of you may know that I am an art lover and so, naturally, SFMOMA is one of my favorite places to visit in the city.
I also love to hang out with my friends during Christmas at Union Square. The Christmas tree and Holiday Ice Rink have become a tradition for the locals!

“Christmas… in San Francisco What a lovely place to be…”

Check it out: Seven Great Ideas of Where to Spend Your Christmas in California

Steep Hill is a very steep street in the city and Chinatown is one of the oldest and most well-known Chinatowns in North America. They are located close to Union Square so that you could just explore all these places on foot.

#13 Coit Tower, #14 Filbert Steps & #12 Transamerica Pyramid

The Coit Tower stands at the top of Telegraph Hill in Pioneer Park. This small structure plays a big role in the city’s history and development.

The Coit Tower was built in 1932 and it offers a great view of the city’s harborfront. Don’t forget to enter the tower as it’s filled with murals created by a group of artists. The public works of art project includes 26 local muralists, they are the precursor to the Works Progress Administration and their paintings depict contemporary San Francisco life.


#15 Lombard Crooked Street

Lombard Street is a long street that dissects the city’s downtown. This is another iconic city highlight that you couldn’t see in any other part of the world – one portion of this street though is named the crooked driving street in the world that puts your driving skills to the test.

In fact, the city boasts some of the steepest streets in the country, and Lombard Street is one of the most unique of the vertically endowed roads and it’s a great photo spot. To have a better idea of how steep Lombard Street is, go two blocks up to Filbert Street and look down over the ridge. Lombard Street is even steeper!

Come put your driving skills to the test as this is still a functioning road that connects Lombard Street between Hyde Street and Leavenworth Street.

These attractions (from Union Square to Lombard Street) may look very close to one another by driving but somehow they are actually not that close on foot. You may park at a few points and group a few spots at each stop. Find a place for lunch on the way, or take a walk to the Fisherman’s Wharf afterward.


#16 Alcatraz

Wow, the Alcatraz. The island is located 2 km offshore in San Francisco Bay so it is not exactly located on the route of 49 Mile Drive, but still, this is so famous that you simply can’t skip this place. Carved by natural and human forces, Alcatraz served the army as a fortress and military prison, and the Department of Justice as a maximum-security federal penitentiary.

Today, this once-desolate island in the center of San Francisco Bay is a national parkland with historic gardens, tidepools, bird colonies, and bay views beyond compare. The former military prison is featured in many literature and movies – from Escape from Alcatraz, Point Blank, to Leonardo’s Shutter Island – which makes the citadel so much more mysterious and fascinating. Myths and legends aside, the island has left some historical buildings behind, and the Lighthouse and Warden’s house outside the Cell House offers an amazing view of San Francisco Bay and the city’s skyline!

Don’t forget to stand by the deck while you are on the ferry, not only you don’t want to miss the skyline that I just mentioned, but also you may spot sea lions swimming in the ocean and wave “hello”~!

How to get to Alcatraz

The first ferry for the island leaves at 9 a.m. and runs between the island and San Francisco at about 30- to 40-minute intervals. In the summer, the island closes at 6:30 a.m. During the fall, winter, and spring months, the closing time is 4:30 p.m. Evening tours are also available. For a full scenic experience, try the Alcatraz Visit with Ferry and Bay Cruise.

Alcatraz night tour

The Alcatraz night tour makes it possible for visitors to experience the island in the evening. Special programs on a variety of Alcatraz topics, smaller crowds, and dramatic evening views of the San Francisco skyline are among the night tour’s attractions. Some sections of the island open during the day are not open at night.

When and why did the prison close?

Deteriorating buildings and high operating costs ended Alcatraz’s days as a federal prison. The last inmates left the island on March 21, 193, and the prison officially closed its doors a few months later.

How many prisoners were housed in Alcatraz? What was the total? The average number?

Alcatraz was never filled to capacity. The average number was approximately 260, the lowest was 222, and the highest was 320. Although 1,576 inmate numbers were issued, the total number of actual prisoners was fewer because some inmates served multiple terms on Alcatraz and there was no consistent policy regarding giving returning inmates new numbers or reissuing them their previous numbers.

How many cells are there?

There are four cellblocks in the prison. A Block was not used to house inmates during the federal penitentiary years. CAlls in B and C blocks were considered “general population.” Unruly inmates were “segregated” in D Block (42 cells), also known as Isolation.

Which cells did AI Capone and Robert “The Birdman” Stroud occupy?

Prisoners were moved from cell to cell throughout their time on the Rock. Al Capone was no exception, and during his time at Alcatraz (1934-1938), he spent time in various cells including a short stretch on D Block (Isolation) following a fistfight with another inmate. He was eventually transferred to a medical prison facility in southern California. Robert Stroud spent no time in a general population cell. After arriving on the island in 1942, he was placed to D Block and in 1948 to the hospital wing. He remained there until 1959, when he was transferred to a medical facility for federal prisoners in Springfield, Missouri.

How many correctional officers worked here?

It required 90 officers to cover three 8-hour shifts and to fill in for those on annual and sick leave. Beginning in the 1950s, the number of correctional officers was reduced due to budget cuts.

Where did the correctional officers and their families live?

Some lived in San Francisco, but many lived on the island. Building 64 included a number of apartments, and there were three apartment buildings, wood-frame houses, and a duplex on the Parade Ground. The warden lived in a large house near the prison building. Some of these buildings were destroyed by fire in 1970, and others were demolished by the government a short time later.

Did anyone ever escape? What about the 1962 “dummy head” escape?

In the 29 years that Alcatraz served as a federal penitentiary, 36 prisoners tried to escape the Rock; all but five were recaptured or otherwise accounted for. Three who were unaccounted for participating in the same breakout, the June 1962 escape, are immortalized in the movie Escape from Alcatraz with Clint Eastwood.

Does Alcatraz have a gas chamber?

No. Alcatraz had no “death row” or any facility for executions.

How many prisoners died here? What happened to their bodies?

Eight inmates were murdered by other inmates, five committed suicide, and fifteen died of natural causes, including disease. Bodies were sent back to family members or, in a few cases, buried in local paupers’ graves.

Does the government plan to re-open Alcatraz as a prison? Is there a modern-day equivalent of Alcatraz?

Alcatraz is now a unit of the National Park Service and will remain so. The modern “super-max” equivalent of Alcatraz is in Florence, Colorado.

#18 Sea Lions on Pier 39

Located in the Fisherman’s Wharf area, Pier 39 is where sea lions reside. Look out for these lovely creatures on shore, enjoy a lovely and warming calm chowder at the Fisherman’s Wharf, and take pictures of the Golden Gate Bridge at the bayfront!

#22 Golden Gate Bridge (view from Fort Mason), and #30 Baker Beach)

Another great spot to view the Golden Gate Bridge is on the other side of the bay. Baker Beach is a popular beach in the city that offers a dramatic scene of the Pacific Ocean and beyond. There are nude areas on the beach also!

The area is an upscale residential area. You may also want to do some house-looking driving down the streets. A great way to travel both sides of the harbour is by taking the Bridge to Bridge Cruise.


#24 Palace of Fine Arts

Not a lot of travelers know about this. The Palace of Fine Arts is located in the Marina District. The monument was built for the 1915 Panama-Pacific Exposition and served as a venue to display artworks and exhibits. The pavilion is the focal point of the site, and it was built in Beaux-Arts architectural style which took inspiration from Roman and Ancient Greek architecture. The Exploratorium Science Museum is located near the site as well.


#33 Ocean Beach (to Golden Gate Park)

If you are taking the long route and driving through Ocean Beach, you simply cannot miss Golden Gate Park – it was a little bit weird to me that there’s not a numbered spot on the Official Map, but you will see its route clearing weaving through the park from one end to the other.

While it is one of the Best Urban Parks in the World, Golden Gate Park is a rectangular-shaped urban park wrapped by one of the American big cities. In fact, it’s even 20% larger than Central Park. The administration work began in 1871, (almost the same time as Central Park), and now, it’s the third most visited city park in the United States after Central Park and the Lincoln Memorial.

One thing that I think Golden Gate Park is different from Central Park, is that it’s a bit off from the city’s commercial district; instead, it’s surrounded by a residential area, and so to me, the park is truly dedicated to the well-being and recreation of the locals.

The park features a De Young Museum (I love the sculpture garden), the Academy of Sciences, and a Japanese Tea Garden. At this point, I would also like to include the Presidio of San Francisco as the park is merely 5 minutes away through the Richmond district.

The park is a former U.S. Army military fort and it’s part of the Golden Gate National Area. The park features a golf course, and don’t miss out on  The Palace Of Fine Arts, an impressive monumental structure originally constructed for the 1915 Panama-Pacific Exposition in order to exhibit art.

#34 Market Street from Twin Peaks

If you do complete the route in the right order, you should be reaching the Twin Peaks almost at sunset, which is a great spot to have a panoramic view of San Francisco.

If you are on the right track returning to the City Hall afterward, you should be passing Castro, and why not stop there for a nice dinner (there are a lot of restaurants with cuisines from the East to the West) or even catch a show?

49 Mile Drive - Castro

#36 Oakland Bay Bridge and #37 Treasure Island 

Another architectural wonder connecting San Francisco and Oakland. The project is a manifestation of architectural achievements and it could be viewed at the Ferry Building or AT&T Park. The bridge goes through Treasure Island, which is a former naval base and now is used for housing and another tourist spot.

49 Mile Drive - Oakland Bay Bridge


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