We did it kind of piecemeal. Wife and I talked a lot about our goals when we got married and traveling was a big goal. We targeted retiring at 50 but didn't make it. At 55 we announced to our staff that we were 50% retiring and started turning a lot of the day to day stuff over to them. Started traveling a lot more and did more extended travels where we would be gone 2-3 months at a time. By 60 I would say we were 75% retired and all the day to day stuff was handled by staff. Fully retired at almost 65, sold most or our machinery then had a clean up auction for the rest of it. Rented our owned land out and helped landlords that wanted us to to find tenants for them. Guys doing the farming for us are doing a bang up job. 

Have not missed it at all and even though we were mostly retired up until full retirement, didn't realize the stress relief there would be when we finally gave it all up. Was a load off my shoulders, especially when I knew all our valuable employees had new employment (they had no problems finding new jobs). 

I think the key for us was we had life other than the farm and plans for such many years in advance of the final decision. Never wanted to do anything but farm (and sell farm machinery for 7 years) since 5th grade and if I count right did 48 crops on my own. That was enough for me. In reality the last few years of our operation it was mainly for our employees rather than us. I think the final decision was made when we came to the realization we were keeping it going for the wrong reason, as there were plenty of opportunities for them outside our farm. We were keeping it going for a reason that no longer made sense.

It all has been good. No regrets. Had fun winding it up and winding it down has been good too. Writing the checks for the IRS was no fun, but at least the pain was short lived and over with after the second year (the sales of all the "stuff" spread over two year period).

Enjoying retirement immensely.