From Melbourne (my home port) south I usually stop at Jensen Beach Causeway either north or south depending on
wind. You can
dinghy in to eat at Conchy Joes on the south side.
Then I go to Palm Beach where there is plenty of
anchoring room. I go inside if it is rough, outside if not. You can go out at St. Lucie inlet.
Trade off is outside you fight the
current, inside you open bridges.
From Palm Beach I go to Ft. Lauderdale and either moor at Los Olas city marina or take a slip during the summer as they are very
cheap out of season. Once again the wave state determines inside or outside. The farther south you get the more bridges. If going inside try to hit from here on during the
work week.
From Lauderdale I have to go outside to
Miami due to my
mast being as high as the Julia Tuttle bridge. I like to
anchor south of Rickenbacker Causeway but there are many options.
My next stop is just south of Jewfish Creek to have dinner at Gilberts. I try to hit here on the weekend. It is a lively place.
I draw 5' and usually go inside on a rising tide to
anchor in Islamorada (usually near The OV or Oceanview, a good little restaurant owned by an ex-Pittsburgh Steeler lineman).
From there, I stop at Marathon and then I usually anchor in Newfound Harbour or off Lois Key with an easy half day sail to
Key West from there.
If you draw more than five feet or just want to avoid the skinny
water Hawk Channel outside is deep and easy. Just not as many
anchoring spots.
Returning home if you get out in the
gulf stream it is a speedy trip!