Considering the time of year, the possible need to sit out wx, scheduling...It might make make sense to "drive the bus" and motor up the ICW instead.
Unless you are looking to equip the boat for offshore use, in which case you may want to look into safety equipment (i.e. life raft
) and plan on spending some time to install and equip the boat before the trip.
If this was a centerboard boat that has had the board modified or sealed up, it may not be suitable for the offshore run at all. Or if it was fixed in the down position, you might not be able to consider the ICW. Post some information, shed some light. Could be useful to you, too.