Hey Matthew,
It's great that you are looking to spend two weeks roadtripping on the island this summer!
I know for a fact that tour-operators offer "fly & drive" or self drive tours formulas, which means the itinerary, car rental and accommodation is prepared, but you still retain flexibility on what you'd like to do in between stops.
We have a few tour operators who have such formulas such as
Gate 1 Travel,
CIE Tours or
Great Value. Here's a complete round up of
tour-operators for US visitors.
Did you have an itinerary in mind for the two weeks you intend to spend with us?
Have a lovely Sunday,
Antoine