Craighouse-Port Ellen-Rathlin -Ballycastle-Ardfern-Peel-Port St. Mary ,should see you OK although the stretch from Oban to Craighouse might make leave you a bit parched in which case add Loch Melford or Craobh Haven.
Long walk back from Melfort but at Craobh The Lord of the Isles is within falling distance of your berth. don't know who is running it this year though.
If you go to Portpatrick eat at "The Crown" the best seafood pancake in Britain....Do not enter in a swell, interesting at night as the 2 leading lights up the side street are disguised by the fairy lights along the front street!!
First time I went in there with a boat was on a wild February night back in 84 whilst taking a Waveney class lifeboat from Fleetwood to Troon...not the same place in February as in August.
Depends on how often you want a pint!
Don't make the mistake of making the trip and missing any of the pubs along the way.... there are too many good ones..... so give yourself a few weeks for the trip!
Hope my advise is helpful! Cheers!