San Francisco is so bounded, so separate, so distinct from its surroundings that entering it can feel like entering a giant amusement park. The city should turn exploring it into a game.
To encourage in-depth, multi-day exploration across many different neighborhoods, the city could create gamified touring courses that, like scavenger hunts, motivate participants to explore widely. Impelled by their natural drive to collect and complete, many visitors would see more, go farther, and perhaps even stay longer.
Jump links
#39 Pilgrim’s Progress: Trip Tracker App
#40 Cabled Conveyances: The 49-K Tug
#41 Trains & Trolleys: The 49-Mile Roll
#42 Scenic Cycling: The Tour de François (49-mile bicycling course)
#43 Pedestrian’s Pilgrimage: Trail of the Old 49
#44 Climber’s Collection: The 49-Peak Experience (mainly for locals)
#45 Topical Tours: Gamified touring courses for specific interests
¯¯¯
#39 Pilgrim’s Progress: Trip Tracker App
The city could make a “Trip Tracker” app that visitors use to navigate each touring course with GPS, hear recorded guides, log selfies from designated photo checkpoints, and share their progress on social media.
When visitors finish a course, they could receive an auto-generated virtual trip log with a two-page spread displaying each leg of their completed pilgrimage. Each spread could show the relevant checkpoint selfie next to a timed validation stamp (drawing the time from the photo’s metadata), plus a map image for that leg and relevant historical information. The last spread could show a city map, with pin images showing each completed stop. Visitors could use the app to order a printed, passport-style trip log, with a portion of the proceeds going to the city.
Visitors who complete all four main touring courses using the official app (the 49K-Tug, the 49-Mile Roll, the Trail of the Old 49, and the Tour de François) could automatically receive an email with a printable, letter-size pdf Croix de François (Francis’s Cross), formed from the names of the touring courses oriented in the four cardinal directions (✚), with an option to order a printed certificate stamped with the seal of the city.
¯¯¯
#40 Cabled Conveyances: The 49-K Tug
Map (shows overlapping segments in one color only)
¯¯¯

The “49-K Tug” consists of all the existing and proposed cable-drawn rides in the city, including the Hyde and Mason cable cars, the proposed Pac Heights and Union Street cable cars (extensions of the existing California Street cable car), the proposed Telegraph Hill Funicular, and all four proposed skyways.
Counting overlapping segments only once, the total length of these routes would be 49 kilometers. This number obviously did not happen by lucky coincidence. I got 49 by:
- splitting cabled and non-cabled rides into separate courses, then
- switching the distance unit for the cabled lines to kilometers, then
- stretching the Bay Bridge Skyway to Treasure Island (I previously had it stopping at the top of Yerba Buena Island).
In manipulating the length to 49, I did not add or subtract lines, or even portions of lines, other than stretching the Bay Bridge Skyway to Treasure Island (which in retrospect seems like a no-brainer, since that’s where the proposed theme parks are). So the map does reflect my true judgment as to what lines and stops would be good to build.
As I did on the fantasy map, skyway designers could fine-tune the total length of cabled lines by simply moving the Treasure Island stop a bit farther out or in. But if the total length of cabled lines actually built does not end up near 49 kilometers, this tour could just be called the “25-Mile Tug”, the “3-Hour Tug”, or whatever.
To complete this course efficiently, riders could make round trips incorporating (a) the Hyde and Mason cable cars, (b) the Pac Heights and Union Street cable cars, and (c) the Golden Gate and Ocean Beach skyways (linking these last two with a Presidio-Land’s End hike).
To coordinate the 49-K Tug with the 49-Mile Roll, riders could take the Six Hills Skyway out to the zoo and return via the L to West Portal, M to Balboa Park, and BART to Embarcadero.
¯¯¯
#41 Trains & Trolleys: The 49-Mile Roll
Map (shows overlapping segments in one color only)
¯¯¯

The “49-Mile Roll” consists of all the train and trolley rides in the city, including BART (from Embarcadero to Balboa Park), Caltrain/HSR (from the proposed SF Central Station to Bayshore), the F Streetcar (including the extension proposed in Idea #4), and all the Muni light-rail lines (J, K, L, M, N, and T, including the extensions of the N and T called for in Idea #1). Counting overlapping segments only once, the total length of these routes would be 49 miles.
I got the total to 49 by:
- splitting cabled and non-cabled rides into separate courses, then
- keeping the Trains & Trolleys course in miles, even after changing the Cabled Conveyances course to kilometers, then
- excluding the Balboa Park-Daly City BART segment (which seemed justifiable enough, since traveling it requires leaving the city), then
- making the proposed T line detour (at Mission Bay) a bit more direct than I first had.
Getting the total trackage between 48.5 and 49.5 miles actually seems pretty realistic, because:
- If the F Streetcar extension (Idea #4) did not come to pass, one could get the total between 48.5 and 49 miles by simply counting the F line’s inbound Beach St track track separately from the parallel outbound track on Jefferson St/Embarcadero.
- If neither Idea #1 nor Idea #4 came to pass, the 49-mile total could be reached by simply extending HSR/Caltrain to the Transbay Terminal (as currently planned) and adding the Balboa Park-Daly City BART segment to the tour.
So with a little creativity regarding how the track mileage is counted, it should be possible to get it between 48.5 and 49.5 regardless of what happens with train routes.
¯¯¯
Downtown detail:
¯¯¯

Notes:
- The map uses the N Judah line (dark blue) to represent the Muni Metro trackage under Market St and north of Duboce Avenue. The green line along Market (between Storrie and Duboce) represents the section of Muni Metro tracks under Market that is not used by the N Judah.
- Where the map shows multiple lines in parallel, separate tracks exist in real life. For example, the three parallel lines along Market indicate the F Streetcar tracks at ground level (orange), the Muni Metro tracks below that (dark blue, showing the N Judah line), and the BART tracks below that (light blue).
- The 49-mile length includes the re-routing of the T line to hit the proposed Mission Bay Station, as well as the extension of the N line to reach that station.
- The 49-mile length counts Caltrain/HSR all the way to the hypothetical SF Central Station at Market & Van Ness. It does not include:
- the currently used segment from Mission Bay to the 4th Street station (which would be replaced by the hypothetical SF Central Station); or
- the map’s proposed “Rail yard access spur” (meant for empty trains); or
- the stretch of track along King that one would need to take to reach the proposed Crossbay Tunnel (even if this track existed, it would be excluded on the same grounds as the BART segment between Balboa Park and Daly City—it requires leaving the city).
- The line distances listed on the map do not match the officially published lengths of some lines, because I cut them off where they meet an already counted section (e.g., I cut the J Church line where it intersects with the N Judah).
To cover the 49 miles (and some of the 49-K Tug) efficiently, pilgrims could:
- Take BART from Embarcadero to Balboa Park, then the M to West Portal, then the L to the Zoo, then the Six Hills Skyway back to Embarcadero.
- Combine the K in a round trip with the J.
- Combine the N in a round trip with the Ocean Beach Skyway.
- Combine the T in a round trip with Caltrain (walking from the Sunnydale T stop to the Bayshore Caltrain stop).
¯¯¯
#42 Scenic Cycling: The Tour de François (49-mile bicycling course)
Map showing selfie checkpoints
¯¯¯

The Tour de François map shows a 49-mile cycling course with 49 selfie checkpoints for the Trip Tracker app. The route starts and ends at the Ferry Building. It mostly follows existing bike routes, but presupposes the creation of a few greenways and bikeways that are proposed in the 49 Or So Ideas map (including segments north and south of Sloat Blvd, and the segment from City Hall to Mission Bay).
The route aims to be as scenic as possible, but prioritizes rider safety and limiting ups and downs. It requires brief dismounted walks in four places, all marked in green on the Google map.
¯¯¯
#43 Pedestrian’s Pilgrimage: Trail of the Old 49
Jackson Square and Banker’s District
¯¯¯

This 49-km tourist pilgrimage pays a photographic tribute to each of the city’s “Old 49 Neighborhoods” (proposed in Idea 47). The figure-8 route allows visitors to complete the pilgrimage in two hikes that each conveniently starts and ends at Union Square, or in four hikes with convenient transit to and from the designated turnaround points.
Pilgrims could use the proposed Trip Tracker app to navigate the Trail, hear a recorded tour guide, log selfies from 49 designated scenic checkpoints (one per neighborhood), share their progress on social media, and order an auto-generated trip log containing their photos, time-marked validation stamps, and historical information on each neighborhood.
I have mapped two possible trails through 49 old neighborhoods:
- The reclassified-neighborhoods version counts the Presidio plus all the neighborhoods east of the city’s old western boundary (Divisadero/Castro) and north of the city’s the old southern boundary (Precita Creek), including the new neighborhoods proposed in Idea 47 (Barbary Coast, Jackson Square, Italian Hill, Theater District, Central Crossing, Sitlintac, Yerba Buena, China Basin):
¯¯¯

¯¯¯
- The existing-classification version uses only existing city-designated neighborhoods, filling out the 49 by adding 7 of the oldest neighborhoods west of Divisadero/Castro (Presidio Heights, NOPA, Haight Ashbury, Cole Valley, Ashbury Heights, Buena Vista, and Corona Heights):
¯¯¯

¯¯¯
The information below applies to both trail versions, unless otherwise noted.
Four-day hiking route:
- Old Coast Trail (maroon): Union Sq ↔︎ Pac Heights via Fisherman’s Wharf, Marina, & Presidio.
- Can be shortened by returning directly from Pac Heights via proposed skyway.
- North Hills Trail (purple): Pac Heights ↔︎ Union Square via non-coastal neighborhoods.
- Old Mission Trail (green): Union Square ↔︎ Dolores Park via central districts.
- South Piers Trail (blue): Dolores Park ↔︎ Union Square via Potrero Hill, waterfront, & Market.
- This is the longest trail but also the flattest.
Two-day hiking route:
- Old North Trail (Old Coast Trail + North Hills Trail; totals 24.77 km in the reclassified neighborhoods version)
- Old South Trail (Old Mission Trail + South Piers Trail; totals 24.19 km in the reclassified neighborhoods version)
Transit options at the turnaround points:
- At Pac Heights: Turnaround point is a stop on the proposed Golden Gate Skyway.
- At Dolores Park: J Streetcar.
Other notes:
- Both maps list neighborhoods in the order in which one would reach their selfie checkpoints if proceeding counterclockwise along the Old North then Old South trails. This differs from the order in which one would enter each district following each route, because some districts’ selfie checkpoints are not reached until the second or third time one enters them.
- As envisioned in the reclassified neighborhoods version, the Trail would skirt seven neighborhoods along their edges, though each would have a suitable spot for taking the required photo.
- Alternate course name: Camino de San Francisco (from Spain’s Camino de Santiago).
- The diagonal shortcut from Terry Francois Blvd to 3rd St is under construction (2023).
¯¯¯
#44 Climber’s Collection: The 49-Peak Experience (mainly for locals)
¯¯¯

San Francisco’s hills are among its greatest attractions. The city could get more tourism value from them if it made an official list and map of “The 49 Hills of San Francisco”. A gamified hiking challenge comprising these 49 hills would be a fun and healthy activity encouraging locals and frequent visitors to discover more of what the city has to offer. It might even cause some hiking enthusiasts to make an extra visit or two to complete their collection.
Forty-nine is as reasonable a number as any. For one thing, counting hills is inevitably an arbitrary business. How high must a hill be to be counted? How prominent? How separate from adjoining elevations? How steep? Must it be on the mainland? Must it lie primarily within the city limits? What about factors like historical or institutional significance? Accessibility? Having a name?
Using various sets of criteria, people have reckoned the number of hills in San Francisco to be anywhere from 7 to 74. Dave Schweisguth’s sfgazetteer.com gives an excellent survey of these reckonings – along with some of the arbitrariness, self-contradictions, and outright errors they have involved. Schweisguth’s exceptionally inclusive inventory lists 74 hills, but contains hills without names, hills that are not on the mainland, foothills and shoulders of Mt. Davidson, hills less than 100 feet above sea level, and minor undulations like “Hippie Hill”. Others have generally excluded such elevations, producing counts that typically fall between 42 and 53, such as those of Tom Graham (53), the anonymously authored Hills of San Francisco (42), Gladys Hansen’s San Francisco Almanac (43), SF49hills.com, and the now offline 47hills.com. If one excluded the five hills on Schweisguth’s list that are either under 100 feet above sea level or not on the mainland, his total would be 69, bringing the average count of the foregoing lists to 50.5. And so if one factors in that Schweisguth’s 69 is a bit of an outlier, it is clear that these lists’ overall center of gravity is very close to 49.
Given this fact, and the inherent arbitrariness of hill-counting, it is perfectly reasonable for the city to define a list of 49 hills to promote tourism. One way to do so would be to apply a geo-mathematical formula and simply set the minimum height at the height of the 49th-highest hill. But to allow at least some leeway for subjective considerations (such as a hill’s historical significance and interest to visitors) I would suggest the more holistic approach given below.
The 49-Peak Experience map lists a set of 49 hills that all:
- are located on the mainland;
- are located primarily within the city limits (this excludes the Olympic Club ridge, La Portezuela, and foothills of San Bruno Mountain);
- reach at least 100 ft/30 m above sea level (this excludes, for example, the hill under the Alice Griffith housing project), and meet this height requirement in their current form (this excludes historic Irish Hill);
- require a person to travel uphill from any direction to reach the top (this excludes Kite Hill, Cathedral Hill, Sutro Heights, Mint Hill, and many others); and
- cannot be reached by walking predominantly downhill from another hill (this excludes various hills including Monterey Heights, Robinhood Drive, and all the sub-peaks of McLaren Ridge).
The last factor introduced a degree of subjectivity into the process, as it involved weighing the vertical distance one must descend from the higher summit, the amount of subsequent climbing required to reach the lower summit (which is influenced by the layout of streets and the presence or absence of man-made structures), and the horizontal distance separating the two summits. However, this subjectivity was always guided by the objective goal of excluding any elevation that could be experienced as a minor interruption of a descent.
I included what I am calling “Italian Hill” (cresting just SW of Lombard & Hyde) separately from the main peak of Russian Hill (Vallejo & Florence) for all the reasons given under Idea 46, but also for the fact that the two peaks are virtually equal in height (which means that one can’t be regarded as a shoulder of the other).
These judgments were made possible by the USGS National Map and Brian Stokle’s clean, color-coded SF topo map at Urbanlifesigns.com (he sells printed versions of it).
References
- Graham, Tom. “City of Hills“. San Francisco Chronicle.
- Hansen, Gladys. San Francisco Almanac.
- Hills of San Francisco (anonymous).
- Schweisguth, Dave. SF Gazetteer.
- SF49hills.com.
- Stokle, Brian. Forgotten Hills.
- USGS National Map.
¯¯¯
#45 Topical Tours: Gamified touring courses for specific interests
The Trip Tracker app could also offer gamified courses for quirky niches like hillside staircases or famous car-chase scenes, as well as for popular interests like architecture, visual arts, civic activism, LGBTQ, film, history, literature, etc.
For example, for military buffs, it could offer a “Pacific Defense Passport” consisting of sites related to military history: Fort Mason, Presidio Main Post, Presidio National Cemetery, coastal batteries, Fort Point, the Military Intelligence Service Historic Learning Center, etc. Including such a course could give a sense of belonging to conservatives who might otherwise feel unwelcome in the city due to their political persuasion.