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Unfortunately, as you've noticed by now, the Bay Area is a mess of different transit agencies that don't really care for each other and don't have a whole lot of regard for the practicality of the rider experience. While there are efforts to improve that situation, it presents some problems for your trip.
The good news is that the BART station at SFO now ...
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Caltrain is terribly slow, so it will take you an hour to ride from Sunnyvale to San Francisco. Evening service is quite limited, and takes even longer (1h20). Be sure to check the schedules before you leave, and plan your day.
If you can't get a Clipper Card beforehand, it'll cost you $16.50 for the return trip between Sunnyvale and San Francisco.
In San ...
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Having a Clipper card would be convenient, as it can be used on BART, CalTrain, and MUNI. In your sort-duration trip, however, obtaining a Clipper card may be more trouble than it’s worth. The challenge is that while value can be easily added to a Clipper card in many locations, the card itself is harder to obtain.
Some BART stations have humans in a ticket ...
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