The OP is probably gone by now but the advice above about sailing to the Canaries or Azores is way off base. I'll offer this in the hope some future reader is not misled.
Uricane, look at a chart of the Atlantic. Boats leave New England for the Carribean every year in early November, passing by or stopping in Bermuda, and then proceeding south to the BVI or points east and south of there. Halifax is two days max to the latitude of southern NE and the angle on the wind isn't that much different. If you're set to the east of Bermuda, it's no big deal as the NE trades will be found south of there.
The route most competent skippers would take if doing this trip non-stop (and that's a big if) is NS to Bermuda (stop if necessary) and then to Bahamas. Timing is challenging, but if going non-stop then leave on a cold frontal passage in early November and beat feet south as fast as possible so you hopefully only have to deal with one nasty gale along the way (odds are that time of year you'll have two). The biggest risk along this route is having to deal with an approaching gale or worse while in the Gulf Stream and/ or it's numerous eddies.
With a 50' waterline the NS -Bermuda leg would take a week plus or minus, and the Bermuda to Bahamas leg a day or two less.
The risk of encountering a strong gale in the Gulf Stream in November is very real and shouldn't be discounted. People have died and boats have been lost doing this passage in recent years. A better approach would be to cruise down the US coast during the summer or early fall and leave from Norfolk in early November.
Using this older post as a continue the conversation regarding a crossing from Halifax to Bermuda.
Currently in Halifax
boat is a Cape Dory 30 MKII 1987 hull# 3
Fitted with new Viking offshore liferaft
Garmin Chartplotter and radar
several tablets with electronic charts plus Bermuda paper charts
EPIRB and personal AIS/GPS beacons
Diesel tank 20 gls
Diesel jugs 4 total 20 gl
Engine Westerbeke 3 cyl well maintained with 2 racors 500 in line with independent connectors to maintain engine running when filters clogged plus a remote vacuum gauge to monitor filters.
Water 40 gl
Jacklines lines from the cockpit to bow,all center installed and extra line from the cockpit to deck around dodger\
autopilot and Monitor windvane
just purchased Iridium go to have communications /weather reports and sign out a routing/weather service when on route
Plus have Garmin InReach explorer II for texting/weather
Me 78 y/o (no comments please)
Have sailed and cruised either short or single hand for the last 40 years
total logged 10000 n/m
last trip 4 years duration from Morro Bay to ST Petersburg via Panama Canal
crew 2 more people aboard with sailing experience
considering a 3rd? the boat is small.
leave Halifax to Bermuda first part of October and leave the boat on the hard to return in a couple of months after tropical storms season.
Why? stay positioned for a possible crossing to Europe or whatever considering my age do not longer buy extended warranties or draw long-range plans.
Advice and ideas sought out,I do not take offense if you point out to weakness
of my plans however, there is a limit due to my personality shortcomings.
The idea to sail coastal going south is considered but not sure in the long run is whort it, just finished motor sailing my boat from Morehead City NC and the tought of going back,well not exciting
thank you in advance