Frankly that would be low, low, low on my list of ways to spend a couple weeks on a charter boat, even if I was getting paid! As pointed out by everyone, it's almost always all "uphill" on that route, no mater what time of year. Coming from the Caribbean to the Bahamas and Florida in late Spring/Early summer can be a lot of fun, but that's a lotta miles to cover in a couple of weeks for one couple and a couple of kids on a charter boat IMHO...and you'll probably be hard pressed to find one.