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Chris 249 said..
I'm biased but I really like the boats around 28 feet. The gear is still light and cheap but they have significantly more room and/or speed than the 23-25 footers. Cav 28 at the top end of the price range, Santana 28, Marauder 27 etc - they'd all be lively enough to sail for someone coming down from an S&S 34, but noticeably easier to handle. The Compasses (Compi?), Folkboat, Top Hat etc are a significant drop down in speed.
The Endeavour 26 could be worth looking at too, although IMHO they are a bit narrow down below. There's a few Cavalier 26s around at the moment too.
That Marauder 27 on eBay a couple of weeks ago was an absolute gift. Unfortunately they only built about a dozen.
"The
Maurauder 823 was designed by Kevin Shepherd who has produced some outstanding boats such as the Marauder 24 and the Investigator trailer-sailer, and this is no exception to the rule. Shepherd planned her as a comfortable cruising/racing yacht to give the owner maximum luxury in a boat of this size without sacrificing performance. And performance she certainly has – in club racing or JOG events. She has berths for six, a most spacious saloon, and sells at a price acceptable for a family cruiser racer. She handles her sizable rig with ease and is comfortable in a seaway.”