I think a more realistic thing that could actually be pulled off would be some kind of weekend getaway on land at some resort in California. Or at a stretch: Hawaii or Cancun, Mexico. A place near a nice beach with a stage, PA system, etc set up to do the nightly entertainment that was done on the original Boob Cruises.
However, there's an issue with those festivities in that a lot of the young and popular big boob models and porn stars do not have the background in live exotic dancing that the women on the original boob cruise did. Can Leanne Crow do a live striptease in front of two dozen horny men? Would she?
Speaking of Leanne, I don't know about some of the names I'm seeing in this thread. Winter Pierzina and Poetry Travis seem like bizarre and illogical choices. The original Boob Cruises were a who's who of the scene at the time. If you want to recreate the original magic I think you got to go for the big guns. You have to get Leanne, Tessa, Jordan Carver, Lana Kendrick, Antonella Kahllo, Amy Anderssen, Candy Charms, Maseratixxx, Hitomi Tanaka, and Gianna Michaels. Everybody on the west coast or people who can get there easily. The industry has moved on from the big implanted girls. The big naturals are the queens now. But a few for variety and old times sake would be great.
Karla James, September Carrino, Lorna Morgan, Rachel Aldana, a few others have husbands and/or kids. I don't think they'd be up for spending a weekend partying with a bunch of (probably single) dudes getting wasted.
But I think it could happen if it was cheap enough for the men and there was a financial incentive for the women. Just going on a free vacation wouldn't be enough. There would have to be a bunch of photos and videos made, probably for Score again, but also for the women's individual websites. No DVD sales. That would be ripped and put up as a torrent on CJ the day it came out.