Hi, liron, and welcome to CF.
I hope you'll get a response from someone with direct experience, but perhaps my limited knowledge may be of marginal help to you.
I planned a November
passage from St Thomas to Marathon Key a few years ago, and was also concerned about having somewhere to "bail out" if
weather became a serious issue. My conclusion was that Ragged was too far out of the way, and the few small cays along the north edge of the Old Bahama Channel didn't look like safe options. I decided that I would carry on without stopping to Cay Sal Banks. If weather precluded crossing the
Gulf Stream there, I planned to
anchor at one of the two semi-viable
anchorages there--Cay Sal or Anquilla Cays. I researched various sources and holding is not the greatest, with currents and scouring, so an anchor watch would be prudent.
As it turned out, my weather routing
service advised me that a tropical wave was approaching from the east and a strong cold front was coming from the west. It appeared that they would collide over us when we were half way through the Old
Bahamas Channel. I elected to turn north through the
Turks and Caicos and take the weather in the open waters of the Atlantic, and was glad I did. We ended up proceeding past Eleuthera and through the NE Providence Channel, crossing the
Gulf Stream from Great Isaac Light to Hollywood Beach, which is just south of Ft Lauderdale.
You might want to consider taking that
route and avoiding the potential issues of the OBC.
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