Florida to the Bahamas

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I have spent quite a bit of time on my own boat in the Bahamas. Having read posts this far, I have a couple questions for the OP:
Eight people with their gear on a 31' trailerable boat?
If you are bring a compressor, why are you worried about shore based fills?
Why wait until spring when the weather windows for crossing the stream are much shorter?
How much fuel do you carry? Is it gas or diesel?
How much experience do your "former Coast Guard and 2 licensed captains" have operating a boat in very shallow water with multiple much shallower coral heads?

And a few comments:
Fuel, water, food and ice are very expensive (compared to the US) in the Bahamas. Fuel is available in the out islands, but I recommend a good strum box if buying fuel there.
There is great diving but some areas are very shallow.
In winter and spring, it is not unusual for winds to stay up for long periods of time, making crossing the stream with a small boat and even diving in some areas difficult to impossible .
 
I just looked at the specs on the boat and I really think trying for the Bahamas is a bad idea for a number of reasons. Can it be done? Sure with the right conditions. But you cannot be sure conditions will be right when you need to make the crossing.

I would like to suggest an alternative that is still on my bucket list and well within the capabilities of the boat. Take it to Key West and dive the Tortugas. It is only accessable by boat and the diving is supposed to be outstanding and you won't have to deal with a long Gulf Stream crossing.
 
Some of the posters have hit on this obliquely, but crossing the Gulf Stream requires planning and a good weather window. If the wind is blowing against the flow of the stream, it kicks up high seas. We waited a week for a good weather window. You will be in a power boat so your crossing will be faster than ours was in a 36' sail boat. We left Lake Worth inlet at 0100 and crossed the Bahamas Bank at about noon. You will want to plan your departure to cross onto the bank with the sun high in the sky. Makes it easier to see coral heads.

Visit some of the Cruiser Forums and you will see many threads on planning and executing a crossing. The best source of weather in my opinion is Chris Parkers scheduled HF broadcasts. Marine Weather Center - Marine Weather Center Services

You don't have to subscribe to listen in on the forecast, but do need a good HF receiver. Just do your research and take care. Crossing the Gulf Stream can be tough. The diving is great.

It's true... any wind with a "North" component (coming out of the N, NE, NW) will build up the waves. Been there, done that in a 32' Tartan with 25' waves...

For weather, a HF or single side band/SSB is needed to pull in the National Weather Service master station out of Norfolk Virginia. Also there are various weather nets such as Herb Hilgenberg (AKA "Southbound II") out of Burlington ON, Canada. BASRA, Bahamian Air Sea Rescue, also has one, but we always found it of limited use.

Bonne chance,
 
https://www.shearwater.com/products/teric/

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