I was just perusing this forum and came across my own post from 2016 as I’ve been planning another sailing trip.

To close the loop, I ultimately did find a great owners time charter that was worked out great for my family and the boats owner. We sailed the Leeward islands from BVIs to Guadeloupe and back - 1k nautical miles, 10 countries, 40 islands - all just prior to hurricanes Irma and Maria. 2 months after our May - June sail, the hurricanes hit and our charterered sailboat was declared a total loss - tragic. However, We had a great time!