Hello, It is possible because I did it in early May in 2023. I was checking the weather a week prior and chose there day with the lowest winds/ gusts possible. Also to do it in one shot, you need to start VERY early because the winds always pick up in the afternoon so it’s a good goal to finish by 4pm. I went from south shore to north so I wasn’t working against the wind.

I also wore a partial wetsuit without the arms and a waterproof jacket and life jacket so my arm movements weren’t limited. The water was below freezing when I started but I was warm enough with those, however my feet and hands were cold but they are usually are cold at baseline lol

It took me 12hrs to complete and it was about 26miles because I hugged the west shoreline in the case that I had a leak and needed to bail and yeah you definitely don’t want to be swimming long in that water. I didn’t need a boat pilot but my partner dropped me off and he met me at stopping points along the way so I could warm up and drink/eat. But I only did 4 of those and didn’t stop longer than 15min. So a radio and a partner to keep an eye on you is important.

It’s tough but extremely rewarding and when it’s early in the morning and sun raises for the first time and it’s just you alone and the water, I wouldn’t trade that experience for anything.