Seeking Weekender Recommendations
While both the Typhoon and the Ensign are neat boats, (both are boats that I have spent a lot of time on at various times in my life) there are a couple issues that I want to point out to you. Both were originally built with out self-bailing cockpits or full floation. Later the designs were modified with the addition of self bailing cockpits. I would try to find one with a self-bailing cockpit as non-self bailing cockpits are subject to swamping and require more attention to keep them bailed out. Although one of the areas that I sailed an Ensign actually was on eastern Long Island Sound, neither of the boats are especially suitable for the light air and power boat slop that is so prevelent in this area. I also would not consider either boat to be especially stable but both are pretty classic designs.
Another venerable design of that era that I have alway liked is the Grampain Classic 22 (and its near sistership the Bluejacket 23). These C&C designed 22 footers are very nice sailing boats in a wide range of conditions. I owned one in the early 1980''s and daysailed and weekended it over a pretty wide area around Annapolis. These are probably the prettiest boats on this list and in many ways are probably the best single-hander except that the lacked a self-bailing cockpit.
I also like the Cal 25 for that kind of thing. They had a good size cockpit and reasonably comfortable accomodations. They are quiet stable good all around sailors. At least down here on the Chesapeake you can often find them in very nice shape for a pretty cheap price.
Also from that era, is the Pearson Commander 25. For only a little more money these were much nicer looking boats than the Ensign and offered a self bailing cockpit and a nice little cuddy cabin that is more suitable for weekending.
The Seafarer built Rhodes Meridian came in an ''overnighter version'' that was a lovely little boat and might work well for you as well.
There were a number of Alberg designs that are closely related to the Ensign. Probably the prettiest is the Sea Sprite.The 23 foot Kenner Kitiwake was a prettier more cruisy cousin of the Ensign. Bristol built a nice 22 footer whose name escapes me.
The slightly later Oday Tempest 23/24(not to be mistaken for the Olympic class Tempest 22) was a very nice little daysailor/overnighter.
While a little later design, the Ranger 23 has always been a favorite of mine in this general size range.
A somewhat classic looking later design that is very much in keeping with you sailing goals might be a 23 foot Sonar which were very popular on LIS.