I'm relatively new to sailing (taken a few lessons, gone out single-handed several times in a 14' rental, and did some sailing years ago in a 19), but really enjoy it a lot....
Considering the above and if you have no time in this boat I'd go the ICW, but question the wisdom of doing this trip by yourself if you have never been over the route, the boat and equipment is new to you, do you totally trust the motor, etc..
Have you been out in the boat for a sea trial and seen that all the systems work and that you are comfortable with them for a trip of possibly two days.
Does it have anchoring gear that is good. Would you stay at a marina at night? Will you be able to dock the boat there?
You need charts for sure and it would be really good to have at least a handheld GPS with waypoints on it to keep you in the ICW if you have any doubts on following the markers.
When we bought our Endeavour we were faced with something similar. We went out for a short sea trial, so I felt confident about the diesel, but I sill put a fresh filter on it. We put up the sails on the sea trial for a short time. The boat is rigged just like our smaller Mac so we felt that should the diesel fail we had a pretty good chance of sailing her somewhere.
It had good anchors, but still we bought an additional one, a Manson Supreme. You need the anchor for more than just staying on the hook overnight. If you had the engine quit on you on the ICW, under a bridge or about any place else you need to be able to deploy one quickly.
We were moving her about 70 miles from Ft. Myers Beach up inside of Charlotte Harbor and could of gone almost the whole way inside, part of it the ICE, or we could of gone up the outside and cut in at Boca Granda. We wrestled with the decision for a couple days while preparing the boat for the trip and finally decided on the inside as being the safer decision for us.
We went that route and ran aground for about 5 minutes on the way at the Miserable mile, but got off. We did have tow insurance and I would for sure suggest that you get the same before the trip.
We had also been over the same route before, so knew it pretty well and had the whole route in the chartplotter along with paper charts.
I don't want to sound too negative, but if you are going to do this I suggest trying to find someone who has made that trip before to go with you. If you had a problem and had to get towed with no insurance you might spend a lot of money. Read the thread on tow insurance on the main board.
Did you give up on getting a boat with a trailer? Is that an option?
Good luck on getting the boat and making the move,
Sum
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