Re: Florida to Bahamas in May
Firstly, crossing the Gulf Stream in any boat is not akin to sailing on Lake Erie and to think otherwise is naive in the extreme.
Further, even with favorable southerly winds, the water between the Coast and the Banks is riven by 4-6 foot waves fairly closely spaced which are the bane of a boat like the Cal 20. On a broad reach in such conditions you'll be very lucky if you can average 4 knots. Considering the average drift in the Stream, you'll be driven a good 36 to 40 miles north in the crossing. At your best average speed, you'll have to steer roughly 090º M to maintain a course to West End from Ft. Lauderdale which will require a good 16-18 hours assuming you're not beset by one or more squalls during the trip which, at that time of the year, is unlikely. You'll either need an iron butt or a wind vane, tiller pilot, or pretty capable 12 YO to manage the boat in the conditions you'll find for such a time period.
If you wish to undertake such a voyage, it would be wise to find another, adult, adventurer to share the experience and the effort; or, to do a heroic single handed sail about which you can bost, and let your children and spouse joint you once you've made the islands (although as you describe her, your wife may not be too thrilled with the sailing on the Banks once she arrives). Note too, on your return trip you're likely to arrive at St. Lucy or Cape Canaveral so you'll have quite an interesting cruise back to Ft. Lauderdale.
Frankly, considering that the Keys are much akin to the Bahamas but are less costly and more easily accessed, it might be wise to do your cruising there, no?
"It is not so much for its beauty that the sea makes a claim upon men's hearts, as for that subtle something, that quality of air, that emanation from the waves, that so wonderfully renews a weary spirit."