Hey Mainstreet, sorry I'm so late in responding. Just been overseas - building a new yacht in Poland. Very exciting! The Deerfoot is now in FLL and on sale. I found the trip to be pretty much as expected from the advice I was given. If you are anchoring in the Mississippi, then make sure you hug the bank and start early to get a good day's run. Venice Marina was a highlight. Great folk around there. Shallow bank near the entrance, but muddy, so easy to motor off when you touch bottom. Exiting the river into the Gulf, I would highly recommend the Main passage. We tried the smaller of the two passages and found depths to be less than the chart was showing, so turned around and headed back up and round to the main passage. Lots of crab pots and lights and oil platforms and such during the first 24 hours in the Gulf, but plain sailing after that. Our draft is 6ft 6" and 87 ft air draft. We had no issues.
Enjoy the trip! BTW we are Kiwis...

Hi Macaway. I followed your thread about landing in N O and sailing to Key West. Are you a US vessel? I'm Canadian and just bought my boat where it is lying near N O. I'm hoping to make the same run in May... 47' Ketch 6'6" draft 60' air draft. Any recommendations?