Foul weather is like anything, you have to go out and practice on it so that when you get caught out you do not get overwhelmed. You have to practice to hone your skills and to keep them sharp. Setting sail on 25-30 knot winds and 5-6 ft swells is energizing and fun; beyond that only if you have to.
25-30 knot winds and 6-8 ft swells is a normal day around Christmas time (some years it's much longer than a couple of weeks) in the eastern Caribbean. We rarely start a day's sail without the equivalent of at least a double reef (we have an RF main), adjusting our sail area further as we get out into the weather.
The Meltemi winds, which blow from about mid-May to mid-September in the Aegean Basin, are also commonly underestimated by visitors who sail there.
It's always easier to shake out a reef than to put one in, so beginning the day reefed is not a bad idea, especially if not sailing in your home waters.