Sailing Boston to UK, when?

There is quite a narrow window after the cold fronts stop coming down from Canada and before the hurricane season starts.

Perceived wisdom says leave in early May but only after having a hard look at what is going on front wise in the North.

This is exactly the issue. Too early the odds of a late season cold front are very high. Too late and the odds of an early season hurricane increase. However, early season hurricanes do tend to stay further south so I would prefer to err on the side of later rather than earlier. One should only do this crossing in a well found boat since this far north the chance of a low pressure system from the north is fairly high any time of the year.
 
There's no good time. The accepted wisdom is mid-May, but that is just when the New England/Grand Banks fogs are at their worst. On the great circle route expect to be in dense fog for days at a time, in a comparatively busy traffic zone.

If I were you I'd start from (and finish at) some place else! :)
 
To quote the High Priest of Offshore Sailing from his "World Cruising Routes", (and my Christmas Present):-
"Eastbound passages from North America are undertaken mostly in late spring or early summer, from May until early July, when best conditions can be expected."
Who of us can argue with God
 
We left Rhode Island 31st May, and Halifax around 10 June in 2013 Almost evryone we spoke to on the other side said we were leaving 2 weeks too early. We waited out the first season hurricane in Halifax and the motor for 48 hours to get past the second. Caught a severe storm about half way across about June 29.

As Cornall says "a cold, wet and foggy passage at the best of times. The passgea to Halifax was foggy and we saw nothing after clearing Nantuacket sound until we saw the lighthouse above us at Halifax. Similarly we had up to 1/2 a mile vis, until we cleared the Grand Banks. First sun was off the Scillies.
 
So what is the best West->East route?

Like most things boating (and life as well?) it's a compromise between negatives and benefits of alternate routes.

Take a more southerly route you are less likely to encounter gales from the north and fog but more likely to catch an early season hurricane. Further north you have more reliable westerly winds, too far south you probably hit calms in the horse latitudes.

One common route is the leave the US east coast to Bermuda. Bermuda to the Azores then on to Europe. The downsides to this route. Bermuda is a bit south and very possible you will run into some calms from the Bermuda high pressure zone. Minimize this by heading N to NE out of Bermuda. Also if your destination is the UK you will have to make some distance back to the north once you leave the Azores. And this route is a good bit longer than the northerly route but you will have a couple of stopovers to compensate.

Northerly route: shorter but higher chance of fog, cold, stormy weather.
 
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