Re: Shannon 28 versus Caliber 33
I can comment only on the Shannon. We have a 28 with the offshore configuration (head in the bow, no vee berth), which we have used for coastal cruising in Maine. Enough room for 2 certainly. We could fit 3 for overnight passages and 4 would be a stretch. We like the large cockpit, where we spend most of the time.
Not the fastest light air boat, but once it gets over 8 kts wind, it is pretty respectable. Easy to handle and is more comfortable in seas than the flatter-bottomed boats I've been on. Pretty heavy displacement for a boat this size seems to help with the motion. The cutter rig gives lots of options in different wind conditions.