What in particular is driving your thoughts about downsizing?
The man has quite a bit of sailing experience, so assuming he is inexperienced is perhaps unjust.
What in particular is driving your thoughts about downsizing?
Certainly it will be a challenge to propose boats to you that are significantly smaller while maintaining headroom sufficient for someone 6'3" as your Hunter 33 essentially has the beam of a 30 footer (10"3"). So, although my S2 9.2A has nearly 6'3" of headroom and decent berths, it wouldn't be much of an improvement. Nor would a Catalina 30, which might actually be bigger than your H33 in some ways with its 12 foot beam. A much newer boat might also avail you of in-mast furling, which may help your sitiatuion, but you will pay for it. For example, there is a newer H32 with main furling for sale at our club, but it is probably a $70K+ boat.
Going in a different direction, a much smaller boat with a pop-top, which would satisfy your headroom requirements somewhat, is unlikely to satisfy your other desires (inboard). A Rhodes 22 has a 6'6" double berth, 6'6" pop top, a walk in enclosed head and a self-tending jib. They have been made for decades and are still available new. But Ct to Block Island on a 22 footer, while doable, might be a long sail for a weekend trip. Catalina 25's were available with a pop-top, a fin keel and an inboard. Finding one may be a challenge though.
So, back to my title. What is driving this for you? Certainly dealing with larger sails is more of a workout, even going from may last boat, a 25 footer, to my 30 footer. Is that one of the issues? If so, have you considered going to a smaller headsail (even perhaps making it self tending) and perhaps adding a second roller with a code zero or drifter on it for light air? Anything you can retrofit onto your boat will likely save you money over changing boats to a boat of similar size. A friend of mine has a Freedom 28 sloop he may sell which has a huge main and a small self tending jib and it is a sin how easy it is to sail. However, it is not suitable for someone 6'3" as I whacked my head twice trying to sit on the settee, never mind standing. If it sounds interesting, you may consider the Hunter Vision 32, with its similar rig, as it will have ample space but be easier to sail. The kicker is that it is likely larger than your 33 and will run you about $40K. Plus build quality of that generation of Hunters is perhaps not up to what you are used to.
Perhaps you could get what you are looking for in a Flicka. But given your physical size I don't understand why a 33 -34 foot boat is too large.
