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When I did offshore passages between NY/LIS to Bermuda and the Caribbean I used the SSB and SouthboundII. SBII is a weather routing service provided by Herb Hilgenberg a sailor and now weather expert who lived in Bermuda for about 10yrs or so (a guess) and is now back in Canada.
At the same time each day (about 6pm IIRC) sailors would come on to 12a on the SSB and report in. Herb would take each sailor's local report and then give his advice as to what to expect and which course to take. I would listen to all the reports to get a more "global picture" of the weather. Many yachts transiting to the Carib, for example would be scattered about from the US east coast all the way to the Caribbean and so his reports and listening to up to 20 or 30 sailors was valuable real time "local" weather from the Atlantic.
He worked with other yachts in the Western Caribean and cross atlantic as well and plotted each yachts positions once they were signed in. This helped in a few rescues too!
I suggest for passages you use a weather routing service (such as SBII) and communicate with SSB or sat phone. Herb's is free, but others charge a fee for this valuable (life saving) service.
I had a weather fax which I found helpful. Now you can receive grib files with an SSB and modem.
Access to weather information has greatly improved over the past 10 years and there are many options especially sat imagery and grib files.
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