Anyone done this trip
I''ve done a similar trip to what your are considering. I sailed my 26 foot shoal draft boat single-handed to the Bahamas. I crossed over from Key Largo, to N.Bimini. As someone else suggested, if possible, I recommend crossing over with another boat.I didn''t have any problems with my crossing, but it''s always better to increase your safety factor when ever possible.
Besides the obvious needed preparation of having necessary spares for your outboard,plenty of food and water,the boat in sound shape,proper charts,etc.,I think the most critical items of concern are your ditch bag, and dinghy.
On a 26 foot boat towing a dinghy can be a problem. I have a 8-1/2 ft. inflatable that I use. It''s too large to store on the bow when inflated,so I end up towing it on a bridle. The arrangement works fine unless you run into bad weather.You should have a plan in place of how you''re going to secure the dink if things go afoul. A dink slamming into your boat can damage itself, or your boat rudder,etc.
A good ditch bag is a must.If the worst were to happen (which isn''t likely if you''ve chosen a good weather window for your crossing) you''ll be counting on that ditch bag to substain you for a few days.It should include: water,food,flares,hand-held compass, fishing line with hooks,etc.
With these prepared items, "It be no problim,Mon!"