This is what I would recommend:

Cooper
Leverick
Anegada
Anegada
Scrub
Cane Garden Bay
Jost Van Dyke
Sopers Hole(clear out of BVI ) not an overnight stop, they do have some nice gift shops
St John
Sopers (check into BVI) not overnight stop
Norman
Peter Island


This route would be less sailing into the wind compared to your option 1 but gets to the same destinations. I suggest 2 nights at Anegada but you can play that by ear.


For seasickness see your General Practice Dr. to get an Rx for scopolamine patch (very effective, minor side effects- dry mouth) I suggest you try one prior to your trip so you know what side effects you have.

Cheers,
Tony