We’ve been using the “2Talk Bluetooth Heatsets” by Sena. They fit comfortably, and the design going around the back of the neck doesn’t interfere with any hats, or my wife’s ponytail. They have lots of range – great for stern tying and not yelling from shore to boat. The earpieces aren’t so tight that you can’t hear ambient noise or others talking, which is nice when docking or loading on the trailer. The only negative thing I can say is my glasses interfere a bit with the over the ear part. Price wise they were the least expensive in the quality brand range (that I could find here in Canada). I have been using Sena Bluetooth intercoms for over 10 years on my motorcycle, and the controls are similar, once on and paired (in 5 seconds) just adjust the volume if needed, no fuss. They hold their charge very well, last year I think we charged them only twice even though there wasn’t a low battery notification.
I see Sena has a bunch of different styles now referred to as “Nautitalk” (great name!). If I had to purchase again from what I know about the 2Talk model, I’d probably lean towards the Nautitalk Open model. Although they look to be double the price, they appear to be lighter, smaller and likely more comfortable.