No bad suggestions given. As you may be aware I make multiple trips every year back from PR to CYOA moving boats after hurricane season on boats as small as 36'. Last year was some of the worst conditions I've encountered taking nearly 11hrs to do the 42 miles on a 40' cat. Typically the worst conditions are from Culebra to Sail Rock. With that in mind, it is only about 10 miles. I've made the trip many times on my previous 31' mono as well. Yes it can be miserable but only for a couple of hours or so. It really depends on the winds. If the forecast is for over 6' seas I don't go unless for a delivery. 6' forecast means 8-12' steep faced waves in the worst area just off Culebra in the shallow water. It sucks, period. You can turn off and sail south which prolongs the agony. I prefer to motor sail about 15 degrees off the wind while trying to go the shortest distance to the lee of St Thomas. Since you will be on a private boat I would aim for Savanah, if not directly into the wind, and then fall off to the south in the lee. I would confirm all the owners are in favor of that. Boats have hit the reefs south of the airport around Flat Cay in the past. That 40' Bene you're on sails and motors well. I would go for shortest route back.