First of all, please don't talk yourself into this being your last trip just the 2 of you, although live it like it is! Hopefully, you will be back, just keep a positive attitude. I realize that there might be extenuating circumstances that I don't know about but I just lost my mom in June and I felt like even when she was physically super healthy she talked herself into being old and not able to do things and she missed out on a lot of fun! And, if you really think it is going to be your last trip, go to Anegada!

If you really want to go to Cooper the first night, without "getting of the dock quickly" stress, use Boaty Ball. Yes, I know...controversial to many reading this post but it did help us when we were there over Thanksgiving week. Luckily I had gotten online right at 7am and booked a Boaty Ball at Cooper for our first night. It was nice to know we had a place to tie up when we got off the dock later than we usually do. It also lets you really learn the boat without rushing. If that doesn't work you could go to Cooper and if they are full go to Norman that first night rather than last.

If you don't do Anegada I agree with Winterstale, use Marina Cay as a halfway stop between Leverick and JVD. The next day check out Diamond Cay, Little Jost on your way to White Harbor or Great Harbor.

You actually don't need 2 nights in Leverick to be able to rent a car and go to the Baths. We have always just gotten up super early the day we go to Leverick (this last trip we went from Cooper to Leverick and got to Leverick by 10:00am) and have a car waiting for us there. Rental companies will bring them to you and pick them up. We had plenty of time to explore the island and get the car back by 6pm. You can even keep it longer if you want and have dinner in town.

Here is one of my favorite itineraries...

1/23: Cooper
1/24: Marina Cay
1/25: Leverick and rental car to the Baths
1/26: Anegada (We always rent a car here because it is cheaper for us when we have our kids. For just 2 you could always rent a moped. Rental is so much cheaper than a cab and you are on your own time and can check out multiple beaches. We like Cow Wreck and Anegada Beach Club but if you have never been there definitely check out Loblolly too.)
1/27: Anegada if you want 2 days. We usually only have time for 1 day.
1/28: Diamond Cay, Jost Van Dyke. Check out B Line, Sandy Spit and Foxy's Taboo
1/29: White Bay or Great Harbor (If the weather is good we like to stay the whole day and night in White Bay but many people prefer to overnight in Great Harbor instead.)
1/30: Norman Island
1/31: Return the boat

Of course all weather dependent and how you feel that morning!