Hi Steve,
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Yes, you can opt in to an upgrade to priority roam when you get further offshore. It will cost $250.00 for a month for 50 Gb of data. Once you get to Bermuda, if you intend staying there (on a safe mooring) through Hurricane season, you can go back to the regular Roam service. If you are just staying a couple of weeks and then returning, your data will probably have to be used sparingly. Not exactly sure whether you have to wait until the physical month is up to convert the package back, or if you can do it as soon as your data runs out. They are not too clear on the details on the Starlink website.
Fair sailing luck on your trip, I did that trip on a Caluber 40 back in 2010.
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Pete Waterson
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S38-2
Oriental, NC
Pete Waterson