I have sunk in all the best harbors. Tipping without flotation is not fun. I rented a 14 foot FG daysailor in Nantucket about 1975, the rental shop was on the newer North wharf. it looked like a good i.e. windy day. I assumed the boat would have flotation. If there were any, someone had removed the plugs for the air cells under the cockpit bench seating and then it left nothing but a center board trunk and a bare cuddy cabin. This wharf was at the north end of most of the harbor and south of Brant point so there were a lot of itinerants, daysailors, et c, to be negotiated when jibing back downwind from the channel, moored each 35-40 feet. After a short sail away from the dock into the wind to the ferry channel and a broad reach to and from Jetties Beach, the return trip required negotiation of all the moored craft. The Coast Guard station had by then raised it's gale warning flag, and I could make no progress to the dock except by short runs and jibes around the moored boats- nothing a novice should have attempted.
The flip over, grab for the ditty bag, soaked camera, soaked fiancé, and no flotation meant that the boat was visible by the masthead only, down at the bow with apparently a bubble at the stern, keeping the latter a few inches underwater. This seemed to happen in all of around 60 seconds. I did get some help from the nearby Coast Guard, with a tow to the Brant Point Beach, where this captain abandoned ship. No deposit, no return. Let them at the shop tow the sucker back. We had flotation devices but not even a whistle. No shortage of spectators there.
The next time in 1982 with my own trailered-in Clark C-Lark in Charleston (SC) Harbor, the city marina into the Ashley River exited via a goalpost-shaped double-sided steel breakwater with walls around 12 feet high, enough to remove most of the wind from the sails of the little sloop. The 15 feet sloop had no auxiliary. The width between the sides of the steel walls was about 50 feet, with ample wind to tack into the breakwater, and get grabbed by the 9 knot incoming tide and fixed in the corner of the upriver arm of the goalpost, after attempting to tack out, capsizing and turning turtle in the process! If I recall this boat had a metal centerboard that descended into the trunk. The sails were up and attempting to sail underwater along with the current. Charleston was amply provided with Coast Guard at that time, and the first launch that arrived took us off and pulled the boat out of the corner shelter of the metal breakwater. But it was underpowered to do anymore than pull the little boat out of the breakwater and into the main channel where the launch and upside down sloop were both being dragged by the filled underwater sails to head underneath the first of several Ashley River bridges, which was a quite picturesque structure but dangerous to both, given the wind and reversed tidal flow. This required radioing for the larger 40+ foot Coast Guard Cutter, two swimmers in the water to flip the boat, which was thankfully a good alternative to cutting the sails loose. My friend the waitress did not want to go sailing with me after that, but apart from her slightly lacerated toe from a screw extending under the teak on the centerboard trunk, she, the C-lark and myself were discouraged but intact. Small boats can ALWAYS use more flotation. As a lake sailor, I picked a bad place and time to launch in Charleston, with insufficient experience for those conditions. Consulting tidal tables (and local knowledge) would have been worthwhile even in a southern location.
I was lucky, and am grateful to the Coast Guard. Next time, I'll tell you about my horses!