Howdy and welcome aboard this forum!
Dreaming of sailing or cruising (power boat) is a nice dream we all share.
Since you mentioned some of your worries, I have a few friendly suggestions:
1. Take the girls on a charter
(not on a cruise
ship) on a crewed sail boat in a nice place like the Caribbean
. This should be fun, adventure every teen should enjoy, sunshine, water
, and an excellent chance to see how they would like being on a boat in such a place. It may just get them hooked on your dream too.
2. Buy a small sailboat (you can buy a dinghy
sailboat used for about $1,000) and take it sailing where you live now. Get time on the water
, and see if your kids
like sailing small boats (lots of kids do). They may get hooked on your dream this way too.
3. Don't wait till you retire to take a trip of a week or so on a boat. With or without the kids, you could join someone else on their boat and see if you really like the lifestyle.
One never knows what life has in store for us. So, enjoy your dreaming, but make some of that dreaming come true now or soon, rather than waiting till you are 48.
Good luck and I hope you enjoy your time on this forum.