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Given a travel related situation, and given a specific question about the situation, summarize the question into a title

Assuming two different trips - one with a current and one without, what is a reasonable speed to assume for a journey?

First - Norfolk, VA to Bermuda to the Azores to Liverpool

Second - Liverpool to the Azores to Bermuda to Norfolk, VA. (funny how I did that, no?)

I'm trying to get an understanding of how fast a regular sailboat, not using power, traverses a wide body of ocean, both with and against a current. A rough order of magnitude for a lesiurely rate of speed is what I'm after here.

As far as size goes, consider a private craft, again, under sail, not engine, maybe 30' - 40'. The idea would be a boat two people could crew and afford :). Feel free to make other assumptions- the idea is to understand if I'm talking days, weeks, or months.

Output:
How fast can one expect to travel in an ocean-going sailboat?