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I have sailed from Newfoundland to the states twice. Lots of head wind and/or no wind. Depending upon time of year. Starting to get late in the season. I crossed from Shelborne to the Marblehead area. About a 36 hour trip.
 

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It took me about 36 hours to cross Shelbourne to Marblehead area.

Now if you do the day trip route, which can be done, then it will be a week or more because you have to up Yarmouth way and cross over and then work your way down the Maine coast.

My thought is that you are weighing two risks. A longer passage in open waters that gets you South sooner and lest time exposure to bad weather vs a series of shorter near coastal passages with high tides and currents that takes linger and exposes your to greater chance of poor weather.

My calculation comes down to the direct route, especially as it gets later in the season. The direct route is like gaining a week.

This may not be the correct decision for you.
 
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