Re: My first day sailer. What do you pack in yours?
You may be underwhelmed by the performance of your American 14.6 exploring the Norwalk Islands in typical Long Island Sound summer wind conditions. The video I saw on the American 14.6 only shows the boat sailing on a reach... With a beam of 6', it may not be fun working to windward. A motor on the back will definitely affect (negatively) your sailing experience in such a relatively light boat. Four adults on the American 14.6 would be quite a crowd. A slightly bigger boat - the 19' O'Day Daysailer, centerboard version - might be better suited to what you're trying to do. A small motor won't impact its sailing performance as much, because it's a heavier boat. It has more sail area (though still not a lot) to move it along in light air. It's relatively stable because of it's weight, and probably much less expensive to buy. Trailering and rigging it shouldn't be much, if any, more difficult than for a the smaller American 14.6, but the larger boat should be able to handle more varied (read: rough) conditions and provide more varied options to you as your sailing horizons expand. A bigger boat is perhaps not as well suited for your lake, but beaching a used boat - since there aren't many docks on the Norwalk Islands - is also much easier on the conscience than scratching up a brand new boat on the rough shoreline. Your kayaking background is serving you well for first aid and backup plans though. In any case, enjoy!