Hi,
I would say Wooten to Wilmcote is 1.5 hours. Day 1
Wilmcote to Stratford Basin is 6 hours (Min) Day 2
Stratford to Bidford is around 3 Hours Day 3
Bidford to Pershore 6 Hours Day 4
etc etc etc
I would say it would not be relaxing as I would recommend a stop at Wilmcote (Mary Arden House Pub) and Stratford for a Day. Bidford is nice and so is Evesham. You never know what unexpected thnigs you'll find either. Lovely villages / pubs etc etc. Nothing worse than not being able to stop and take time. Also raining days come into play, busy locks, broken locks etc etc.
I know the route well, drop me a PM if you need more info.
Enjoy!
Neil