Before reviewing boat specs, you need to review your own sailing "specs". Going from a 26' MacGregor to a 31' or 33" whatever make is a big step. Since, I too, am a solo sailor, and I found a world of differnece between my 27' Hunter to my 34' Hunter. I don't know your age and physical abilities (BTW, I'm 63) but you need to consider how the boat is set up for single handed sailing. PBreezer has good points about the 33 considerirng solo sailing.
I had a tiller on my old boat and everything was within arm's reach. Going to a wheel and probably a mid-boom rig is more challenging when the weather wants to get nasty real fast. It's a long walk up to the clutches in order to dump wind fast on a big boat. I sail Lake Michigan and we've been known to get an ugly blow without warning. I just hate leaving the wheel to pop the main sheet at the clutches. It was easy when the traveler was behind me. Harken hasn't yet been able to figure out a solution to getting my main sheet at my fingertips.
Now, on the pro side of "boatfootitis" aka bigger is nicer, I was on a guy's 30 foot O'Day and it was claustrophobic in comparison. I could hold a dance in my cabin but I felt like I was bouncing off the walls in his, so to speak. On the off chance you allow people aboard that have no "boat sense", a bigger boat is better for them too. They can get lost aboard and thereby leave you alone which is probably why you enjoy solo sailing like me. Bigger cabin = more comfortable cruising.
Go to a show: kick rudders; ignore the touristas as you sit in the boat and ponder. You're there to make a decision. They're just dreaming. I've overheard more wives talk about how "purrddy the kitchen is". Do you really care about that stuff?
Remember, you're part of a minority breed... a solo sailor. Think about your safety, your ability to handle the boat without help in any condition you might encounter and still enjoy it; not just when it's a nice 10- 12 knot breeze.
I've been doing this on and off for over 20 years. but this is still just my humble opinion. We all keep learning as time goes on. My guess?... You'll go for a 33'. Boatfootitis is an addiction.
Last edited by BigBoatSailor; 11-29-2006 at 08:18 PM.