I have done this trip both coming and going this year, and in a Cheoy Lee to boot.
I did a direct open sea passage on the westbound trip. Had a good forecast on WindyTV and headed out. 49 hours sea buoy to sea buoy at 8 knots. It was a beautiful passage. I came in at the Gulfport Ms channel and followed the ICW from there. In my opinion, entrance to the lake through the Rigolets is the only way to go. Its a well marked passage, stay close to the north shore until you pass under the I-10 bridge then direct to the railroad bridge and hwy 11 bridge then head for the north draw of the Causeway bridge. From there, head for the Tchefuncta river entrance keeping at least a mile offshore until the entrance buoys line up. You will go further west than you think you need to but when you turn North everything will line up nicely.
I had gone east earlier in the year along the ICW all the way to Appalachacola then offshore to Tarpon Springs. It took me three months to get there but that's because I was enjoying the trip so much, I kept stopping for multiple days at each town along the way. The offshore passage portion of the trip was about 17 hours and we had lumpy seas.
I have done the offshore passage portion in December on three previous occasions. Always had uncomfortable lumpy seas. If you have stabilizers it will help. The boat will take much more than you can.
Here are a few pictures taken during the offshore trip.