engine for great loop

[ozarkshark]

I just recently retired and am playing with the idea of doing the great loop. I am looking at boats around 27 feet, so I can tow with my truck, I am about 2 hours from the Mississippi. Looking at several pilot house type sail boats, but those with an inboard diesel are kind of few and far between. I was thinking that an outboard engine would not hold up for a complete loop trip? Does anybody have experience? I currently have a 22 foot starwind sloop, but I have mainly just did long weekends, it would be more like camping, and it has an outboard for power as well.