Contessa 38 v Victoria 34

The Dawn (figures from sailboatdata) offers a SA/disp ratio of 22.13 compared to the Contessa 38's 15.29 and from my experience has better light wind performance. It also offers more/'better organised' space below and wheel steering (the Contessa with tiller can suffer weather helm). Arguably, the Dawn has better close quarter handling but many (not all) were home completed so variable quality/finish below.
That 22.13 will almost certainly include an overlapping Genoa and therefore isn’t likely to be an accurate comparison. Otherwise that’s an insane number for working sails on this type of boat.
 
Given that choice, Contessa 38 ... bigger is better.

Most sailors would be surprised at the minimal wave height needed to roll a boat. Andrew Claughton (who co-authored the University of Southampton, Department of Ship Science’s report) writes in Adlard Coles’ Heavy Weather Sailing, “During the model tests that were carried out to investigate the problem, when the breaking wave was 30 percent of the hull length high, from trough to crest, it could capsize some yachts, while waves to a height of 60 percent of the hull length comfortably overwhelm all the boats we tested.” So, the starting point for a breaking wave to be dangerous to rolling a boat is one that is only 30 percent high as the boat is long.

Waves and your boat
 
So the Contessa 38 SA/D of 15.29 is based on adding the main and foretriangle - the usual way of making the calculation. There’s very little info in the Dawn 39 but I’m 99% sure the figure of 22.13 includes the overlapping genoa. Someone with a set square could probably sort it out based on the drawing but I’m guessing while the Dawn 39 does have additional sail area, the true SA/D based on working sail area would be around 16-17 ish.
 
"Tough choice! The Contessa 38 is the clear winner for performance and speed—it's basically a stretched Contessa 32 with more power. However, if you want a more modern, 'sea-kindly' cruiser with a better layout for living aboard, the Victoria 34 (Chuck Paine design) is hard to beat. Contessa for the thrill, Victoria for the comfort."
 
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