When I sold the sailboat I did not have time to race or even cruise, I made several pacts with myself to use it. But, I didn`t. Then I knew it was time, it became an unused degrading depreciating asset, better converted to $.
You have to be sure. I came back to boating post retirement, and enjoy it. Your situation, having retired, and thinking it may be time, is different, but some of what went into my earlier withdrawal from boating may help.
Island Gypsy 36 Europa "Doriana"