Day one: Plymouth to Salcombe
Day two: sailing around Salcombe
Day three: sailing Salcombe to Dartmouth
Day four: sailing up to Totnes on the Dart
Day five: sailing from Totnes to Brixham or Torquay
Then I will need to sail back again as I can't work out how to get the trailer up to Torquay. The missus, rightly so, doesn't want to tow a trailer up there, having never towed anything before. I think the sail back could be done in two days depending on the weather with a stop off overnight in Salcombe.
My other thought is to go west and drive down to falmouth. Camping at Falmouth, I could then do sails over to and up the Helford. A sail up to Truro or one of the other creeks sounds nice as does a sail around to Mevagissy or Fowey and back. I could easily soak up a week down there as well.