A Sonar would be a good selection on LIS. Kirby designed it to specs provided by Noroton YC, so it has ample sail area for the Sound''s usual light air, but enough ballast to stand up to a strong breeze as well. Various fleets would allow for some racing fun, while the cuddy provides some shelter when weather heads South if you''re daysailing. (There''s probably even room for a porta-potti!) The Colgate is similar, but not as prevalent on LIS, so racing outlets might be limited, and therefore resale value. Soling fleets on the Sound have been reduced to about zero, (we had more than a dozen at our club - but that was about 30 years ago!) so their resale value is also pretty low. That said, we used our Soling for daysailing w/infants, children & friends for many years,(as well as racing) and certainly got our mouney''s worth out of it. The lack of
seats made it less comfortable than a Sonar.
Seats are great if you hae kids because they provide a stage they can climb to and see from without immediate danger of falling overboard. On a Soling, they''re on the cockpit floor, bored, or on deck, about to fall in. The generally light wind on LIS keeps hiking he Soling to a minimum, but if you need to hike, it is WET and really hard on the Abs and legs. (The coaming around the cockpit or the gunwale cuts into the back of your legs, depending upon whether you''re using regualr hiking straps or sitting out on the topsides.) The Soling should out-perform either of the others, (up to 30 degrees apparent upwind, and will turn a 360 in its own length), and they''re a blast to sail. (
We planed for 7 miles once, up at C.O.R.K., but that''s another story.) Solings are lighter and offer fewer amenities for family outings than the other two might. If the price is right, of course, any boat is better than no boat, but with your background & experience, a Sonar might offer the best options for you.