East Coast USA.. Your favorite transient stops???

Rail bridge at New Haven just inside the lock.
Usually not an issue but that rail picking up.
Get the latest chart chip for the lake, That dam dawg-leg past the middle can get confusing.
Watch your wake as you approach Ft Myers, Water Cops (#%$^&%) everywhere down there.

Noticed your bridge clearance above. Hope you can take something down on the top or you will have issues in the Erie Canal and the fiberglass guys will love you. Erie canal lists bridge heights on web site.

Yes, Erie Canal lists minimum bridge height of 20'6. The first low bridge is just North of Troy, NY. Now, everytime I've gone through the Erie Canal (3 times) the minimum height has been around 21'6. But you cannot bet on that.

As others have indicated, you need to make sure you have the ability to reduce your height if needed. If you're coming down the Erie in the spring when it first opens, you might find some of the bridges at their minimum heights, high water mark. It looks like just your mast and what is on it are at issue. What exactly on your boat is over 20' and what would it take to lower it?

If you are on the inside from Southport to Charleston I would skip Georgetown and stop short at Bucksport. Years back I had to stop there due to a mechanical issue. I am glad I chance happened in there. By far the best service and food on the ICW. They really bend over backwards to make your stay enjoyable. Now I always make the stop there. It is one of those off the beaten path hole in the wall gems.

I just wouldn't be on the inside through that area if I was in a hurry.

Good point, but if weather forces a couple of days in the ditch I would stop there.

Well it depends, the OP has a 16 knot boat, so in the Carolina's and GA running outside to safe water and back in is so far, could mean less headway in the direction you plan to go (North) than grinding away on the ICW for the same amount of time. Also the OPs boat is small enough he can run at speed in a lot more places than your boat can.

For example Georgetown,SC to the sea buoy is 16NM, that's an hour at cruise for the OP. I'd rather grind away 2 extra hours a day on the ICW, save a ton of fuel, and not have a boat to rinse and chamois and fuel at the end of every single day and make the same distance in this situation.

Any thoughts about Lincoln Harbor, as opposed to Liberty Landing? I stayed at Liberty Landing once, and it was very nice, but I've heard good things about Lincoln Harbor...

I made the trip from Point Pleasant NJ to Ontario when I bought the boat, also in the spring, after a torrential rain storm inTroy, and made it under all bridges etc without issue--closest call was about 4". Highest point is the anchor light, which can easily be taken down if needed.

Ran from northern Lake Michigan to Beaufort, NC last fall on delivery Cruised at 30mph, left Liberty Landing at 9am and had to head up the C&D due to rough water. Still made Chesapeake City with enough time to take 800 galloons before sundown. From there took a long down running to Coinjock, at your speed you may want to stop in Cape May, the Chesapeake City. From there a stop in Norfolk would probably be next unless you want to take very long days. Run from Coinjock to Beaufort would be a day for you, as it only took me 4.5 hours, but like mentioned a lot of no wake. Beaufort is a great place to stop and spend some time, stay at the city docks if you can.