For this post, I want to talk about a few best practices for making this a fun, joyful practice that you might adopt for yourself.
1. Choose a city with a transit pass, and buy it for the right length
Transit is usually actually cheaper than driving as a lifestyle, but it feels different: usually you pay for a car upfront (rentals, purchase price) or in the background (depreciation, gas, etc.) and you pay for transit ride by ride. But a transit pass flips this around, making marginal trips free. Obviously this only really applies if you've got the right timeline available for a pass: buying a monthly or annual pass for a 3 day visit isn't cost effective!
But if you can get a daily, weekend, or weekly pass, or whatever is similar to your visit time, it can unlock the whole city for a (usually) reasonable fee.
I did this in Paris and Amsterdam last year, and it made things infinitely easier. I particularly appreciated how these cities have passes that cover multiple modes of transit, so I could take for example an Amsterdam tram and the metro on the same pass, or a Paris tram and RER.
Some systems work this differently: London does sell day travelcards, but for Oyster and contactless you can also just tap until you hit a daily cap without pre-purchasing a pass, and once you hit the cap marginal travel is free like with a pass.
Either way, finding a place you can not be concerned about how much each trip will add to your cost is a good start. I'm looking at you, San Francisco: BART doesn't offer passes.
2. Choose a well-connected city
I mentioned above that I like to use the transit to visit places that aren't just traditional tourist areas. But to do that, transit has to go to places that aren't just tourist areas in a useful way: no Detroit People Mover that's just downtown (though in Detroit that might not even be a tourist area) or Seattle Monorail that only has two, very touristy, stations.
To do this, ideally, you want a city where the transit is used by actual residents, so tha you know it'll take you to a wide variety of places. Big cities aren't the only ones that do this, but it does help. Fortunately, a good system often means a good travel pass system, though not always, which is why I put these separately.
3. Choose a city with good transit timing
See my last post on the Metra for what bad transit timing can do. You don't want to explore somewhere only to get stuck an extra hour or two because they don't have a train back--especially if you only have 24 or 48 hours in a city!
This doesn't always or at least only mean purely good frequency, though turn-up-and-go service levels are ideal for this. It means reliability, both in terms of on-time performance and not cancelling trains or buses. And it means timings that fit your schedule, whatever that is: frequent service that starts after you need to be somewhere or ends before you want to leave doesn't help all that much, but a less frequent but better-timed service might help more.
The actual implementation of this kind of tourism isn't too hard: get on a bus or a train or a tram and find a place to get off and explore--or find a place and then figure out the transit to it. But in order to do it enjoyably and without too much worry and expense, I recommend these three priorities for picking a place to do transit-based tourism.
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