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More or less anywhere you are likely to find hotels and pubs with live Scottish music (and loads more with horrible musac). There are too many to list and anyway they keep changing what they do and when. There is no particular one that I am knowledgeable enough to recommend but there are a couple of festivals in September - one on Colonsay and the other on Jura. And Islay has a jazz festival, also in September, which sounds fun. And there is the Islay Festival of Music and Malt in late May every year. As festivals are all the rage for pulling in the tourists I imagine there will be more and more as the years go by.
I imagine most boaties would not be wanting to go to the cinema unless the weather was really really horrible, and anyway there are very few to go to. The Phoenix (apt name) cinema in Oban has reopened after a massive fund raising effort. Tiree may still have a community cinema which is struggling, in Crossapol Bay which is too far to walk from any of the anchorages.
I have only once managed to catch the mobile Screen Machine. Since 1998 it has served a very useful purpose indeed, and surely should be supported, because it travels on a truck around various locations in the Highlands and Islands including Tobermory and Gigha. It's the only fulltime self-contained mobile cinema in the UK.
if you are into films you must also look at Scotland the Movie Location Guide which tells you were various scenes were set in the many movies which have used Scotland as the backdrop from the 39 Steps to Harry Potter to Braveheart and more recently Skyfall (that is the last but one James Bond if you live on another planet). Visit Scotland got in on the act in 2015 with their rather 'gushing' website featuring films showing off Scotland and encouraging tourists to visit.
I think there is only one theatre, and it is wonderful - the Mull Theatre just out of Tobermory. Go there.
The Mendelssohn on Mull Music Festival happens in July and is worth catching if one of the venues is convenient for anchoring, like Duart Castle, Salen and Bunessan.
The Corran Halls in Oban, an unattractive 1960s flat roofed affair, has various visiting shows as well as conferences which you can track on their website.
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The iconic black and white film from the 1940s, set on Mull