From a trailer sailor who camp cruises with a 19ft Mariner.
In my neck of the woods (Albemarle Sound), the feds gave up surveying the sound except for the Intracoastal Waterway 20 years ago. So charts are not that accurate anymore. Still, I carry charts, especially when I trailer to other areas. I study them to get a feel for the area before I go (charts of Core Sound NC, Long Island Sound).
Can't read the water in this area for depth, but a depth finder only tells you depth where you are at, not where you are going. With a 10" draft (board up), I can easily tell when I'm in too shallow a) with a boat hook over the side, b) the centerboard and/or rudder begins to drag (both kick up). I use Navionics on my cell phone because they integrate a huge number of soundings from fishermen's depth sounders pretty accurately. Good enough for me to pay the $50 annual subscription fee. The fishermen depth sounder incorporation net me very good charts of lakes, as well as poorly charted coastal waters. Displayed on my cell phone, along with GPS course and speed, and forecast track, I have all I need for navigation besides the Mark 1 eyeball. Navionics Boating app also lets me lay out desired courses and tracks, and will show me progress against those tracks.
In my old age, I don't crane my neck so well to look up at the masthead on a regular basis, so the Windex that came with the boat has been left off. I have red yard on the shrouds and backstay about 6ft up. When the sun fades the yarn, I simply replace it. Sails have red and green tape telltales to get trim correct. I have learned to feel when the boat is in the groove without even looking at the telltales.
In addition to the cell phone, I have a handheld VHF-FM that I used in Connecticut to get bridges to open. Have a tiller clutch that allows me to latch and lock the tiller in any position. No electrical system yet - a battery lantern and fan suffice for the cabin, and a battery lantern tied to the forestay and hoisted about 6ft up suffices for an anchor light. No electrical system yet, but will probably add one this year or next to power CPAP, and recharge electric outboard battery and phone. Battery powered portable running lights suffice - I don't sail or motor much at night, but AA batteries are supposed to last about 20-25 hrs of use.
In 1979, DW and I cruised the northern Bahamas (starting from Miami) for 4 weeks in an ODay 25. We didn't have Navionics or cell phone or GPS, but we did have a handheld RDF, a compass, and a fixed VHF with masthead antenna. Back then, I used a battery powered lantern on the forestay for an anchor light, and a solar heated bag of water suspended from the boom in the cockpit for our showers. Cooked on a portable propane camp stove in the cockpit, after selling the useless and dangerous alcohol stove the boat came with.
Keeping it simple - which is the fun of small boat cruising.
Fred W
Stuart (ODay) Mariner Sweet P
Hertford, NC