Besides a well founded boat, in my mind weather is the most important factor to take into account. Weather conditions dictate the skill level one needs to travel safely. So … here are a list of sites we find useful.
1. Buoy weather (Most detailed)
We use this site to check wind and swell heights. This can be used globally.
Wave Model: http://www.buoyweather.com/wxnav5.jsp?region=FL&program=wxChartsB&zoom=10&latitude=24.5&longitude=-81.75&zone=-4&grb=wna&gs=wnawave&tau=1&lat=24.5&lon=-81.75&units=e
Wind Models: The GFS model (first link) tends to push out further into the future
GFS: http://www.buoyweather.com/wxnav5.jsp?region=FL&program=wxChartsC&zoom=30&latitude=24.5&longitude=-81.75&zone=-4&grb=wna&gs=gfswind&tau=1&lat=24.5&lon=-81.75&units=e
NAM: http://www.buoyweather.com/wxnav5.jsp?region=FL&program=wxChartsL&zoom=5&latitude=24.5&longitude=-81.75&zone=-4&grb=wna&gs=conusnamstream&tau=1&lat=24.5&lon=-81.75&units=e
2. HyCom.Org
This site is something I use in conjunction with BuoyWeather to figure out what the Gulf Stream may be doing and for crossing the Bahama Bank.
Overview page for what the gulf stream and local currents are doing: http://www7320.nrlssc.navy.mil/hycomGOM2/keymia.html
What to look at for gulf stream and abnk info: http://www7320.nrlssc.navy.mil/hycomGOM2/navo/keymiaspdcur_nowcast_anim30d.gif
3. Passage weather (Most accessible)
This is a much more “user friendly” site than either of the other two. It’s good for a quick hit.
4. NOAA Hurricane Tracking Center
This site is good for regional text weather reports as well as tracking tropical weather graphically: http://www.nhc.noaa.gov/