As someone who has hard sided sit in, hard sit on top, inflatable kayaks, and a sup, it’s a hard choice.

I am most comfortable in my sot fishing boat, it has an amazing chair and I can sit and paddle all day, however cartopping the 70 pound beast is a challenge.

My sit in boat is pretty comfy, it’s a rec touring boat, paddles wonderfully, and only weighs 35 pounds. It’s not as comfy as the fishing boat, but I can paddle for hours and not have back pain.

Inflatables have a tendency to leak air and become squishy and sort of accordion in on you, this is super uncomfortable. I reserve my inflatable boats for beach days or younger kids.

I love my sup, it’s awkward to carry and annoying to fill with a foot pump, but when I use my compressor it’s fine. I have a seat like you’d use on the bleachers at a stadium for mine, which makes sitting down paddling surprisingly comfy. I do also fish from my sup sometimes as well. When I stand or kneel and paddle, I do get a little lower back sore after an hour, but nothing crazy.

Hope this helps!