It occurred to me that there is another option you could consider. On day 1, head northeast out of Crystal River to Cedar Key and spend the night on the hook. On day 2, head south out of Cedar Key direct to Anclote Key. This will wind up being an overnight sail, so time your departure out of Cedar Key so that you'll arrive at Anclote the following morning. This is the route that many take heading south, to avoid the shallows closer in-shore; there are a number of accounts on-line posted by folks who have made this passage. Granted, an overnight passage can be a challenge, and I wouldn't call this an "easy" one, but you'd be in the company of two other boats and it's a relatively straight shot down the rumb line to Anclote, so you'd have a real sense of accomplishment when you arrive at the southern end. Our overnight passage on our trip was Suwannee to Apalachicola, and it wasn't fun - winds/waves were double what was predicted and right on the nose, and it turned out to be the coldest night of the month. But it was a special feeling when the sun rose the next morning and we were right where we had expected to be.
Day 3/4: spend time at Anclote. Perhaps on Day 4 sail up from Anclote to Hudson. Day 5: Hudson to Crystal River.
As Peter says, watch the tides. In late April last year, we could not navigate the channel at Hudson at low tide, and we only draw 2'10". We saw a lot of fishing boats waiting for the tide to come up, to leave out of the channel. Also be aware that all the channels between Hudson and Suwannee, are long, narrow, shallow and bordered by limestone ridges and/or protected grass areas, neither places you want to run aground.
Tides are particularly important if you depart Hudson to head north on the return leg. You need to pick a day with early morning high tide, so that you can get out into deep water and begin sailing north, with sufficient time so it's still daylight for the arrival at Crystal River.
We greatly enjoyed our trip. We left Hudson and went into Yankeetown on the Withlacoochee; from there by-passed Cedar Key and went into Suwanee; and from there did the overnight to Apalachicola. Then we went into the ICW and went to Panama City, Destin, Orange Beach and home to Mobile Bay. Mostly motoring since the winds were on the nose the whole way; and had to sit in Suwannee and Panama City a couple of extra days to wait out weather. Of everywhere we visited and looked into below Apalachicola, we'd like to do Cedar Key someday; and we'd return to Suwannee (a neat little "Old Florida" town and lots of anchorage possibilities in the river) and Hudson. The folks at Yankeetown were great, but there was nothing really there.
Mike Turner
Lazyjack 32 schooner "Mary 'Lis"
Mobile Bay, Alabama