There's no wrong choice when choosing a route for your boat hire holiday on the Shannon, Ireland is a small country and the landscape is pretty much the same all through the midlands.
The Upper Shannon has some of the best activities and pubs/restaurants on the Shannon - award winning cuisine in the Cottage in Jamestown to home-cooked meals on Cox's Steakhouse in Dromod. Lough Key Forest Park is worth a visit with some great family-based activities, and Shannon River Adventure on Kilglass Lake near Rooskey will keep you busy for the day - you'll sleep well afterwards! You can moor your hire boat in the forest park, and Shannon adventure will collect you if from Rooskey.
There are cosy pubs all along the upper Shannon, many with live music at weekends. Traditional music sessions are getting harder to find, but are available periodically in Leitrim Village and Rooskey. Kilglass Lake and Grange Lake near Rooskey offer an isolated atmosphere, not much here but water and tranquility.