Sailing on the Hudson: Cold Spring to Manhattan - am I nuts?

Alright so I've been sailing my Hobie wave on a small lake in NY state, not far from the Hudson river for what will be the second summer.

I was doing some maintenance on it and talking about how I wanted to drive it down to the Barnegat Bay and sail there, and he put the idea in my head of sailing the wave from the closest marina (Cold Spring) down to Manhattan, where my parents have an apartment.

It's about 50 miles, and gets pretty narrow in sections. I guess I have a few main questions that I'm looking for answers to:

1. What's the farthest I can expect to sail the Hobie in a 12 hour day?

2. Are there any rules/regulations regarding little sailboats/Hobies sailing in a commercial channel such as there is in the Hudson

3. Has anyone ever tried something like this?

Thanks!

I recently did a race in a Sunfish Down the CT River that was 12 miles. We started in almost no wind, so little we all held on the the start boat and when they said "GO!" we let go. The wind built to just under 20 by the finish. It was all up wind, down current. The CT River is very narrow in spots. I finished in about 3 1/2 hours. There were two Hobies in the race, a 14 with a jib, and a 17 with 2 guys on it and racks. The 17 finished about 45 minutes to an hour ahead of me, the 14 finished about 15 minutes ahead. I was ahead of them for much of the race because when it was really light the Sunfish was more reactive and I'd say I was a mile ahead when the wind built. Plus there was a bridge they had to wait to open for a few minutes. If we had had wind all the way they would have been so far ahead I would never have seen them after the first bend in the river. But 50 miles is tough to judge. With the right wind it will go fairly quick, one day. But if it gets light or is all upwind you might need to plan on an overnight stop somewhere. I have been thinking of sailing my Wave in the Everglades Challenge, 300 miles over 8 days. My goal for day 1 would be 68 miles, the distance to check point 1. This summer I am going to a test run on Lake Champlain and try for 30 miles.

jbh1126, i have sailed in good wind about 7 miles over 2 hours along a winding river on a getaway. you have the current going with you until you get to the tidal portion where the wind vs. current makes for strange dynamics. i estimate your trip would take 2-3 days in 12 hour segments.

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getaway on long beach island, nj