I think watching for the tired signs is the right way to go. It will fall into a loose routine and this has worked very well for both my boys who are both very good sleepers now.

It has been harder with Tom, as Jack's activities (playgroup etc) inevitably happen during Tom's sleepy times. When he was younger Tom would just sleep in the car or the sling wherever we were, but at 5 months he doesn't do this so easily now. This doesn't cause a huge problem, it just usually makes it a little harder to get him down for the next sleep (and makes for a grumpy boy for a short while). Like others have said, if Tom has had a particularly disrupted time I will skip Jack's activities to let TOm sleep, otherwise we do our normal thing.

So most days Tom will go down about 30 - 60 mins after waking up and sleep for 1 - 2 hours. Then some awake time, then he goes down about 11am. Jack has lunch and goes down for his nap, both boys will mostly sleep until 3 or so which is fabulous. Then some playtime all together, baths and by then Tom will be really tired and go down for the night (between 4:30 and 5:30pm usually). I give him a dream feed before I go to sleep and he will either sleep through or wake for one feed around 3am. Then wake around 6am and we start again. Jack's activities are all mornings so this is where the disruption occurs, but then we have all day to make up for it.