i was thinking jan-march as thats my slow time of year (i repair lawn equipment)
I would love the keys in the mid of summer. For me the hotter the better and i only plan on sailing mornings anyway. I grew spending all my summers on the beach and although i was never on the water the strong afternoon storms always put a damper on my beach activites. I've been in tents and pop up campers while waiting on what was left of tropical storms to blow by. I'd hate to be on any boat in unprotected waters during situations like that.
I've seen 6-8ft waves on the west coat of florida during weak tropical storms. Waters that are usually as calm as glass, i grew up visiting myrtle every early spring and those waves in the gulf were violent enough for me to want to stay away from the water. It takes a pretty sizeable (eastcoast) wave for me to want to keep clear of the water.
I definately need to look into the weather patterns of the keys much more in detail before i set a trip in stone.
Spring is out as this is my busiest time of year and i will be busy all year until july or aug (depending drought conditions) and anytime before x-mas is pretty much out because of family traditions.
I'm guessing if i plan a trip during the winter months i really have to watch for weather patterns of the jet stream
This year we started having insanely warm weather in march with only a few cold spells dipping into the south every few weeks just to remind us it's still not spring just yet.
Id hate to waste a trip down there only to have the cold weather follow me south.
My last winter trip to florida was in the winter of 88. I don't remember much about it other than everytime we'd stop to set up camp the next morning the cold front would have moved farther south.
We spent the entire trip trying to stay south of the cold front.
by tiresome northers i'm guessing you mean cold fronts that bring bad weather and attract surfers to the gulf.