336 - Many Choices
I am in my 4th year with a 1995 336.This boat comes with two different interior setups, and two different mainsheet/traveller setups. So, you can wind up with a very different boat depending on which options you choose.First and foremost, the 336 has the no-backstay B&R rig. This means that you have a very large, full-battened mainsail with a large roach. The headsail is a fractional 110 percent jib. This boat has swept back shrouds that make it impossible to sail lower than a broad reach because the boom can't be pushed out. In practice, even a broad reach involves the main laying (and chafing) against the diamond shrouds.After dealing with the 336's sailplan for four years, while racing on a more conventional Frers 33 once a week, it's more clear to me than ever that the B&R rig is difficult to manage, easily and quickly overpowered, is plagued with excessive weather helm, and has significant disadvantages downwind.The 33.5 seems to have the split backstay masthead rig that marks other Legend types. This sailplan is probably less powerful in light air than the B&R, but I believe it is easier to manage. This boat can probably be sailed wing-and-wing (the 336 cannot), and you might even be able to adjust mast bend.The 33.5 has a cabintop traveler setup, similar to many other boats in the same class. The 336 has this type of traveler on some versions, but many were made with an 18-inch traveler on the steering pedestal. I would recommend that you avoid the steering-pedestal mounted traveler on the 336. You'll have sheets flying around in the cockpit, catching on the throttle, ripping your GPS off its mount, etc. On the other hand, there are only two winches on the factory 336, so having the cabintop traveler must involve some serious winch gymnastics. So, I would try to find one with a mainsheet winch installed or be prepared to install one yourself. The 336 has an unusual interior setup available, where there is no bulkhead between the saloon and the vee-berth. You just climb over the setee and you're in bed. We have this, and like it. There is also a conventional interior available, with a forward bulkhead.When you look at these boats, the 336 will have a lot of appeal with its large, circular cockpit and just by the fact that it's a newer boat. There's a ton of headroom below, and the interior is bright and comfortable. I've never been aboard a 33.5 so I can't speak to that.Would I buy a 336 if I had it to do over again? Nope. I'd probably have a Catalina.Paulsv Escape Artisth336