Two weeks should do it, if you can do at least one or two overnights. There are plenty of good overnight harbors in the Keys and on the Florida
coast, but you'll want to do some cruise
planning to make sure you can find an anchorage or a dock
every night if necessary.
As for your route in the Keys, I'd try to get from Key West
to someplace like Cudjoe or Big Pine Key first night, then Marathon, then Islamorada, then Key Largo
. These are all pretty short hops, and nice spots to overnight. From Key Largo
to No Name Harbor in Key Biscayne is a longer hop, but easily done in a day. After Key Biscayne, just head
up the Florida Coast... stay outside to avoid the bridges and speed limits.
Do your overnights when the weather
is favorable. You might be able to use the Gulf Stream
to pick up a couple of knots ...... I think you need to be at least 5 miles off the coast to catch the Stream.