Originally Posted by
davidrr16
I've done LCY to Waterloo a few times with a checked bag no hassle at all. Best option (as said above) is definitely DLR to Canning Town and Jubilee into Waterloo. There's escalators so it's no hassle with trying to combat stairs with a bag.
Note that if you value convenience over time, make sure you get a DLR to Bank rather than Stratford (trains alternate) - straight down an escalator at Canning Town, rather than steps down, along a passage and escalator up.