I sailed out of Holland for many years. Lake Michigan spoils you. No salt, no tides, even no compass deviation to speak of. I took the trip across Lake Erie and the Erie Canal about 10 years ago when I moved back to NJ, so this info may be a bit dated, but I don't think they moved the canal.
You probably know the first part as well as I do. From Muskegon to Macinaw is 2 or 3 days. Leland is a nice stop. If you go there say hi to my daughter at the Crib. If you want to anchor there is a nice protected anchorage near the park dock at South Fox. Macinaw is, of course, Macinaw.
I can't help with the run down Lake Huron. I had my boat shipped to Monroe and went from there. I was on a mission, so I didn't do some of the touristy things like the Lake Erie Islands. I did Lake Erie in three days, stopping at Cleveland and Erie before entering the Erie Canal. A third stop at Buffalo would have been advisable, since I entered the Erie Canal late in the day and got off to a bad start, as I describe later. A word of advice. Be sure you take the Black Rock Canal from Buffalo Harbor. In one of the stupider things I have survived in my sailing career I went down the Niagara River, following a tour boat. 6 knots through the water, 12 knots over the ground. Scared the hell out of me.
When you enter the canal you will have to unstep your mast. Mine was already down, but the standard stop seems to be Wardell's in Tonawanda, NY. You will have to buy a pass for the canal. For more info see:
New York State Canals: Faq
It's about 360 miles and goes through 35 locks. One of them, Lock 17, is, if memory serves, at 40.5 feet the second highest lift in the world after the Panama Canal. Like being in a concrete canyon.
Starting from Erie, I got into the Canal too late and ended up tying up to the canal bank when it got too dark to continue. This end of the Canal is amazing when you realize they only had shovels and mules. It goes for 30 or 40 miles through a rock cut about 40 feet deep. The next day I made my first stop at Fairport, where I bought my canal pass.
I won't go into detail about where to stop, since that depends a lot on how hard you push. Nothing moves on the Canal at night so you can tie up to the bank, although I was never really comfortable doing so. You can usually stop for the night near a lock and the towns come often enough that you can find fuel. The Canal system gives you a map showing a lot of information about facilities. The map, which you'll get with your pass shows the distance between locks so you can plan your days. It took me 5 days to get across.
Where you stop depends on your schedule. I was on a mission, so I didn't do any sightseeing. In general, however, it's pretty dull. I singlehanded it and, at one point, was so bored I was saying hello to cows.
The locks are a thrill, especially alone. I generally took two lines, one fore and one aft, and ran them around cleats to the center of the boat so I could keep her next to the wall. The turbulence is surprisingly strong. You'll finish the Canal part of the trip with the Chain of Locks down to the Hudson. This is a series of locks, one right after the other, that drops you down to the Hudson.
Your next issue is, of course, your mast. If your boat isn't too big, there is a do-it-yourself crane provided by the yacht club at Castleton on Hudson. For a nominal fee (I paid $35 back then) they let you use their crane to step the mast. There are usually other people there who, in exchange for reciprocity, will help you do the job. My 30 footer went in with no problems, with a little help from my friends.
You'll enter the lower Hudson at the Federal Lock in Albany. By now you'll be a locking pro and, from here down, the river is deep, wide and tidal. I honestly don't remember, but I think I took two days to get to New York, anchoring on the side. If you're not used to tides be sure to get tide tables and try not to fight them. If you must go against the flood, stay closer to shore. It doesn't run quite so hard there. Don't be surprised if you see an ocean going cargo ship coming around a bend. The river is deep water navigable all the way to Albany.
The ride down the Hudson is beautiful, passing through the Adirondack Mountains past West Point, the Tappan Zee, under the GW Bridge past Manhattan. There's a Marina at Liberty Landing in Jersey City with a great view of Manhattan. You can even, if you're so inclined, catch a ferry to Ellis Island and Liberty Island. Just don't bring your Swiss Army knife. The security on the ferry is just as bad as the airports.
Now you're in New York. If you push, you can do the trip in a little over 2 weeks. You can anchor out most of the time if you're so inclined until you get to New York. In the Canal you'll be hard put to find a marina, although some of the towns have public docks. Your biggest cost will be fuel and food. From here you've got the Jersey shore and Delmarva before you get to Mile 1 of the ICW in Norfolk. There are ports along the Jersey shore where you can duck in (figure three days minimum NYC to Cape May) but after Ocean City the Atlantic side of Delmarva is not sailboat friendly. The conventional wisdom is to go from Cape May up theDelaware to the Chesapeake and Delaware Canal, then through the Chesapeake Bay. I haven't gone that way but I have done the outside and my advise is, don't. Not unless you're in a hurry and have crew to make the run offshore in one leg from Cape May. The Chesapeake is longer and I've only seen it from the shore side, but it's beautiful.
The ICW is a whole subject in itself. I've made that trip twice and it's grand. I'm sure you can find plenty of people who have documented it on the Web. From Norfolk both times, it's taken me about a month.
That's a very broad overview but probably has enough detail to let you do a schedule that suits you. Be sure to get a Waterway Guide for marinas, fuel stops, anchorages and other info. Good luck and enjoy the journey.
Cape Coral, FL