I took my family on an 8 week sailing vacation in May-June 2017 which was reasonably well documented in these forums. So, I know the process well - possibly as well as or better than anyone honestly.

For what its worth, it took me the better part of 6 months of planning to pull the whole thing off, but it was well worth it. (And by planning, I mean near daily effort.) However, part of my complication was that I wanted to travel a fair distance - we ended up visiting 10 countries, 40 islands, and covering 1k miles - beginning/ending in Tortola.

I'm happy to discuss, in person, my process. It was a unique "partnership" direct with the owner of a charter company managed sailboat. That was just before Irma, so we were fortunate and the fleet was much larger, meaning significantly better availability. Frankly, unless you booked well in advance at near full retail rates, I can't see how you could pull it off for a December - March charter. Honestly, just getting any contiguous 6 week period during that season would seem nearly impossible, in my experience. Getting any significant "term discount" would seem extraordinarily challenging, as well. My opportunity worked out well for everyone - me, owner, and charter manager.

I did speak to Ron at Seabbatical but nothing in that fleet was appealing to me even though I liked Ron and the concept of Seabbatical. As information, in my very massive and very wide search for a "mid" term charter company or option, I found nothing other than Seabbatical in the Caribbean. That being said, one idea that was pitched to me was to take 8 weeks on a couple of boats "stitched together" - 2 weeks here, 2 weeks there, etc. That absolutely was a non-starter for me given my logistics and interest, but its worth throwing out to you.

Mike, I didn't know that Seabbatical was sold - if that's the case, I'm not surprised, but I am curious about that.

Kevin