I started from scratch, no sailboating experience, grew up on the water around commercial fishing. Fell in love with 2nd boat I looked at, a 1975 Newport 30' MK2; very spacious and made a great liveaboard; the draft was a bit deep for West Central FL, especially around Tarpon Springs where I purchased it. All around Anclote Island are shallows; while my first time out went great--from Tarpon to tip of Clearwater--the 2nd time wasn't so great; I saw on a chart deep water on the lee shore of Anclote (not yet knowing the danger of a lee shore) sand had shifted, boat ran aground, being anvilled, I put out anchor and winched it; fortunately guess the older boats used more fiberglass as it survived; tide came in, now night kept bumping ground every where I went and now it was high tide so if aground
I set anchor; next day heavy winds made pulling in anchor, memorable, no gloves, ropeburn. Worked briefly for a guy who had come down to haul his trimaran the Running Cloud, which was some big deal, long time ago, won a Trans-Atlantic race back in '87. Nice guy, had sailed around the world, prior to racing. Told me never to head out when chance of storms and to never run spinnaker single-handed as if weather changed too hard to take down. I ended up doing both simultaneously: I left Tarpon Springs in the winter with a storm on the other coast and ran my spinnaker thinking I'd use the wind to my advantage; wind shifted, boat very suddenly went to capsize, spinnaker tore before going over. Live and learn. I mention these things to perhaps educate beginning sailors. After my horrible shallows experience off Anclote I knew I needed a depth sounder, and got one; was piloting and varnishing a 1929 Dawn Cruiser in exchange for dock space but little pay, did get the depth sounder though, which saved me from what would've been the end, about halfway down St. Petersburg the shallows jut out so if following the coastline it goes quickly from 40' to well I saw 7' and headed outward. Got to Sarasota, which back in 1990 had a great free anchorage in a cool town; before so crowded, regulated and red tides. I even beached my boat during a high soltice tide painted the bottom, and another time to repair my motor's shaft that my dinghy's line got caught in. Not too long after reaching Sarasota an early morning storm broke my mooring line and I awoke to waves pushing boat ashore; found a emergency tow guy hanging around; we had a tough time getting it off and he assumed I had insurance which I didn't but recommend it if you can afford it; so gave him my depth finder as payment. After that I learned all I could about anchoring, storm anchoring in particular. My liveaboard neighbors got tired of hearing about anchoring; I'd row over to the big international sailors and pick their brains; came up with a good 3 anchor system, well kinda 4 the storm anchor being a 35lb Danforth on 15ft of 3/8 chain w' a 5lb danforth at the end of that so the little anchor would take the stress off the storm anchor. We ended up having a big no name storm come thru at night summer '93 I was aboard with some friends--we had no idea a storm was coming, it was perfectly calm. Watched many boats go ashore that night, I never doubted my mooring. Boat was called a racer cruiser type, wide with a fin keel; extremely maneuverable considering how wide it was, but didn't stay on course well over open waters; single-handedly sailed down the coast along with a friend who had built a big ferro cement sailboat in Mass; he had been stationed in Key West Coast Guard and liked to go down there, I really didn't want to go there, wanted to go to Ft. Myers but thought I'd wing it. Turned out this pitch black storm was right off the 10 Thousand Islands; watched my friend sail into it, was ready to go, then common sense took hold and I headed out into the gulf; missed the bulk of the storm, sailed wing to wing, was great waves so high boat almost was out of the water sometimes. Next morning absolutely NO wind, not even waves and too far out to use my little yanmar diesel, so eventually got some wind--I used a 180 genoa, good sail size I think. But came in a bit south and mistook Marco island for Estero until I came to the bridge which did not seem as high as it should've been for Estero so I anchored and was going to run a line down the bridge to measure it when a local told me where I was, so went back, anchored off Sanibel that night, came into the little anchorage off Sanibel, nice summer there, was born there always wondered what it would've been like to have lived there. Every night people would watch the lightning off the coast so was worried coming back, attached a length of cable off my rear stay, better than nothing. Was heading into the wind sailing back so took some dramamine, tied off tiller, and next thing I knew work up dead of night, dramamine had knocked me out; but seems a boat heading into the wind holds course pretty well; was like that whole trip back. On my way down though--I never used my harness which I seriously suggest people doing--was a calm night, no apparent waves, took little hop off front of cabin to fordeck, but boat had slid down wave I guess as I landed almost off the boat; no trailing line, dinghy aboard, no lifevest, so on my way back I trailed the dinghy behind me; no bad weather, anchored overnight off Siesta Key until morning as the channel coming into Sarasota can be difficult. The rest is the daily life stuff, bicycles routinely getting stolen, even once locked to 2 posts off a fishing boat's signage; the cut thru one post and cut cable of the other; tried for awhile hooked up a bike rack to back of dinghy took bike with me but impractable; speaking of the dinghy, 2x the line rubbed and had to swim to shore for it; 3rd time some drunk kids swam out and used it to row home shortcut to Siesta, Marine Patrol returned it. After that I started using a cable and locked it. Had a bad run in with Marine Patrol once, I'm sure many are fine but in my opinion they have too much power for too little training. Think things have improved from the days of their cutting into people's boats with sawsalls; still my 2 cents is to avoid them. Um, what else? Always tie off large items when transfering from dinghy to boat due to waves/movement. I took out the alcohol stove, replaced with propane, wanted to touch up the heat resistant paint job, tied it off first time, this time no noticeble wind but right when transfering, over it went, thru out my little weight with bouy attached to some line--this is good to have in case drop something overboard--but in the case never found it. the bottom of Sarasota Bay has deep layers of silt. I ended up with just a propane stove top and always turned the tank valve off. Wasn't much good for heating as water is released from propane and water would drip down inside hull getting cushions etc damp and musty. I like to read so did a lot of that, not a big partyier. If you are thinking of anchoring out be aware that the boat will swing and rock most unpleasantly, especially in winter; I think for me that was the worst and perhaps the fin keel made that more of an issue--though I did find a fin keel was easier to get off ground, could get under boat along with anchor and winch tight and lift with waves; especially if a kind motorboater helped
Food was the first issue I remember; had bought a bunch of canned veggies, didn't fill me up; took some time to learn what canned and dry goods worked out, pasta, mac and cheese with tuna fish, hearty soups like split pea, clam chowder w' ritz crackers filling. Eggs never went bad; oatmeal was a great find, so inexpensive and a big bowl kept me full and energetic all day.
Rowing was usually a hassle as the wind shifts I always seemed to get it against me going to shore and coming home; same with cycling; sometimes took so long to row home I'd just zone out until bumped the boat; stopping for an instance would set me back 10-30ft. I got out of sailing right as the red tides were starting in '94 awful when a storm would blow the red tide into bay, dead bloated fish; another thing to consider depending where you're planning on going.
Summer of 94 I went with some friends to Boulder, CO; loved the low humidity; sold boat moved there for college. All in all I think the years I spent on my sailboat to be some of the most formative ones in my life and while youth doesn't offer as much wisdom it is more pliable. I hope some of this might be useful and if you have any questions feel free to ask.
May the wind always be at your back,