You probably don't want to hear this but better you know what to expect. Having lived aboard and delivered boats over many years there will be some scary times.
1) Make sure you have UPDATED paper
charts, ICW chart
books are OK but you MUST update them
2) Have at least one
GPS chart plotter display
3) Download
charts for every smartphone on board and know how to use them
4) Up north the scariest thing will be the big ships, stay away from them and call them if you get worried about their intentions
5) Experienced skippers, including myself, will tell you sailing at night is the least stressful but to the inexperienced, it can be VERY stressful so don't do it in the ICW until you comfortable
6) Don't even consider doing a channel with shifting sand at night, this is mostly a
Florida problem, and try to have the sun aft with someone on the bow
7) Narrow inlets WILL have VERY strong currents and standing waves at times so make sure you calculate the slack times
8) Understand the bottom when
anchoring and use the correct
anchor type, too heavy is better than to light, set it well and always set an
anchor alarm. I could write a book on anchoring as most new cruisers don't even set an anchor without it chafing on the bow roller.
9) Keep the
radio on channel 16 unless you are anchored, and get the
weather forecast at least daily
10) Have a FLOATING ditch bag near the
companionway with a
VHF in doubled
freezer bags, regularly changed spare
batteries and several small dive lights that use the same AA
batteries. Reflecting tarp, sunscreen, sunglasses, hats, seasickness suppositories and other drugs I won't mention (just lookup what fighter pilots use)
11) Coastguard flairs are
cheap and keep you
legal but make you have some Solas ones (hand, parachute, and smoke) to actually use (many years out of date are OK so try to get them second hand and know how to use them)
12) Have some kind of dingy and an abandon ship plan, I won't get into the argument what is best
12) Take either the Coastguard Auxillary or
Power Squadron course
I could go on but you get the idea
-Vic