Exploring the Options

I looked at a couple of trailerable boats like a 23 O'Day but decided that if I'm not prepared to drag the boat back and forth, why not look at something larger. 

One of the primary things I need to consider is draft.  If I really want to spend most of my time gunkholing rather than off-shore sailing, I need to limit the draft to 4' or less.  For the most part, that leaves shoal draft, centerboard and wing keels.

Boats with wing keels offer a shallower draft but they're generally more tender.  When you run around, as you invariably will in the Outer Banks, the wing makes it difficult to get the keel loose.

I want a stiff boat that doesn't heel much in moderate winds   I still have hopes of getting June to join me on board.

I've had it with leaning over the transom to raise, lower, start and shift gears on outboards.  I'm ready for an inboard and diesels are more dependable and fuel efficient.

As far as steering is concerned, a tiller gives you a better feel for what the boat is doing but wheel steering  generally offers more usable cockpit space and better placement of navigation instruments.  I could be comfortable with either but I'm leaning toward wheel steering.

I've been considering an O'Day 27.  They have a great reputation as both a cruiser and a racer.  The 27 has an encapsulated fin keel that draws 4' and is reputed to be a stiff handling boat.  I talked to a sailmaker in New Bern who raved about his O'Day 27.  He and his girl like to spend several days at a time on his boat.  He told me that he would opt for a 28 or 30' just to get the convenience of a shower.

                                    

Unlike the 27', both the 28' and 30' O'Days were made with shoal draft and centerboard keels. The centerboard version draws 3'3" and the shoal draft 3'8".  Both are reported to be stiff handling boats.  I'm not sure which will point higher into the wind.

A roller furler with a 135 -150 percent genoa would be a plus.  

Most boats in this size range have a head just aft of the v-berth in the bow.  At best, it offers minimum privacy for the occupants of the v-berth and head. At a certain age, most of us can't make it through the night without at least one trip to the loo.  

I've seen a few boats with heads located aft near the companionway but they all seem to be on boats with wing keels like the O'Day 280 and 302. Whatever arrangement I end up with it will be better than the porta-potti stored under the companionway in the Sanibel.

Time to look at few boats and see what the marketplace has to offer.