Enjoy bluewater sailing?
The basic routing is as you imagine it (tho'' shaped by the frontal systems as the passage unfolds), but the timing isn''t. The run to Bermuda is subject to frontal systems passing regularly, and the deeper the lows sweeping across N America, W to E, the deeper into the Caribbean the fronts penetrate, and the stronger and colder the winds. Thus, waiting until the end of November, you are lining yourself up for the late Fall frontal wx systems while enroute. Perhaps not as big an issue as if you were headed there from New England, but still problematic with the clocking winds, cold temps and heavy air. (I imagine it to be like some departures from SF Bay enroute to Hawaii for the first 4 or 5 days). So...too soon and you risk a tropical storm; too late and you bounce and shiver your way to ''tropical'' Bermuda.
The late Spring period is preferred but offers its own dilemma. Spring wx patterns can still have lots of deep lows, e.g. in both 2003 and 2004, Spring ''lasted longer'' than normal and so there was a lot of frontal weather most boats had to wait out. Then the snag is that you are arriving in Bermuda with one eye already on the calendar and its upcoming storm season. Bermuda is a wonderful place and quite cheap to visit by boat (assuming you provision well); it deserves more time than most boats feel they can give it.
While you''ve probably used SSB Nets on your Pacific passages, you may not know about SOUTHBOUND II, the call sign of Herb Hilgenberg who conducts a daily HF wx net for boats all over the Atlantic and enroute the Caribbean. (Yachts, tugs, commercial ships, F/V and R/V; it''s quite amazing). No one knows that stretch of water like Herb and, if you have a SSB aboard, you might want to consider listening in, or talking with him while underway. His service is free, but most of us like to send a small donation and a postcard of thanks; if you saw his elaborate station, you''d appreciate how much effort and investment he makes on our behalves.
www.rhadc.com/yachts.htm for an extensive Yachtsman''s Guide for sailors voyaging to Bermuda; lots of good poop in there
www3.sympatico.ca/hehilgen/vax498.htm is Herb''s website
www3.sympatico.ca/hehilgen/weatherman020309.html is the text of Peter Jennings ABC News story about Herb; nicely done