I think part of your question is missing: "What is your favorite Scottish and why?" There should be a noun after "Scottish." Town, area, island, meat pie, etc.
If you're going to be on Skye, then Talisker would be your best bet, since you're going to be there anyway. As far as distilleries go, the distillation process is pretty much the same. It's the water, special ingredients, and casking that make the difference. So unless someone in your party is a true connoisseur of whisky, one distillery will suffice.
As far as traditional music goes, what is your definition of same? Some people define "traditional" Scots music as ceilidh band music with accordion and fiddle (Jimmy Shand, for example); as well as singers like Andy Stewart, Peter Morison, Calum Kennedy, Kenneth McKellar, or Moira Anderson. Others define "traditional" as folk bands like the Battlefield Band, Tannahill Weavers, Ossian, Malinky, Manran, Skippinish, Tide Lines, the Mackenzie Sisters, etc.; or solo performers like Norrie MacIver, Davy Steele, Karine Polwart, Emily Smith, Dick Gaughan, Arthur Cormack, Steve Byrne, Sheena Wellington, etc.
There is plenty of live music to fit either definition. The former can mainly be found at "Traditional Highland" nights, laid on at fancy hotels; the latter can be found at folk clubs and festivals throughout Scotland. There are also various folk music sessions throughout the country, where amateur (and professional) musicians get together for a few hours to swap songs and tunes. The Edinbane Inn on Skye is one such venue for these sessions, as is Hootenanny in Inverness.
There are two small folk festivals going on in mid May. One in Moniave, in the Borders, on May 10th.; and one in Strichen, near Banchory, on May 17th. Folk clubs usually met on a specific day once a week, once a month, or every other week. You can usually find updated folk club information through the website of The Living Tradition, Scotland's traditional folk music magazine, or by listening to Celtic Music Radio www.celticmusicradio.net
p.s.: In addition to Hadrian's Wall, you may want to check out the Scottish version. The Antonine Wall, started in 142 A.D. during the rule of Antoninius Pius, stretched across Scotland from the Forth to the Clyde. Several portions of it remain, especially in the Falkirk - Croy area.