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I think, for the most part, sailing a bigger boat is easier. Except for docking.

I took ASA classes on 34' boats last summer and when I did my first charter this May I got a 39' boat. I did OK, but none of my dockings were quite to my satisfaction.

Shortly after that trip I put my new-to-me Catalina 22 in the water and spent all summer sailing a couple times a week.

This fall I again chartered a 39' boat and my docking was perfect! Just right.

My little 22' weighs max 3000 lbs full of soaking wet people and the 39' Beneteau was probably more like 20,000 lbs, so they are obviously very different things to dock, but I really think my summer of practice on the small boat helped out a lot when it came time to bring the big one in.
 
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