Q: How is Cape Air with the “golf bags” coming from CT to my buddies house on island?
A: My experience is this: Cape Air will get your gear here and probably not charge extra. However if a flight is full they might not be able to fit the bag on and they will prioritize it down. So if I am flying off I usually try to send my gear over on the boat so I know it will be there at the same time as me. But coming out it doesn’t really matter that it arrives on the same plane as long as it arrives soon after.
So it shouldn’t be a problem.