Boat buying criteria; can you help us?

[KeepInTune]

We are 2-3 months away from purchasing. I would love your suggestions on boats to consider?

Sailing background: We are Midwesterners who have been sailing for years. I've been sailing Lasers and Hobies on the wild winds and waves of Lake Michigan for years and have a great respect for the water. We are also coastal cruisers who have chartered and cruised for 10 years (ASA trained as well)....just not on our own boat --until now. We are buying a monohull and will use it throughout the year on our many trips to Florida, vacations, eventually using it as our Winter retreat.

Criteria (not rated in any particular order of preference) :
--Monohull. Sloop or Cutter 38'-44' range.
--Age range: 1988-2008. Condition and upgrade requirements play a huge factor here.
--Purchase location: I'll look and buy anywhere from Annapolis to Houston -but prefer in Florida's Gulf side knowing that I will sail it to our base in Tampa or Ft Meyers area (tbd).
--Budget: $110k US for boat including needed upgrades. This is our target.
--Cruising areas and use: We will cruise Florida's Gulf Coast and FL Keys our first 2 years. We will eventually (3+- years) head to Bahamans and then target Turks & Caicos and VI's. No Antartica or even Atlantic passages in our plans. These are week-long trips, weekend trips, and a few trips longer. Some overnight passages, but mostly nights at anchor.
--Hull shape and Draft: see cruising areas above...(but also see below). I've run aground plenty and don't like it. I've also sailed crappy/stubby poorly designed low-draft winged keels. My slight preference is a skeg-hung rudder and fin keel --but trade off's might have to take place here.
--Sailing style: I'm happiest when I know my boat is trimmed and running at a nice speed. I don't like tugboats and I enjoy slicing through at a good 8-9 knots (i.e. efficiently sailing up and passing a weekend charterer). But also don't like pounding in seas --who does.
--Interior: 2-cabin owners-type layout. (this is my wife talking here!) 1) comfortable aft cabin -queen-ish size if possible, 2) a nice head w/shower, 3) comfortable 2nd cabin accommodations when our non-sailing friends/family visit for a weekend island hopping voyage, 4) decent working galley (no special requirements).
--We're open to either center or aft, though preference goes to aft cockpit.
--Sugar scoop stern is most enjoyable for our fishing/diving/swimming enjoyment, however this understandably may be a trade-off.
--Lastly: the boat will have some ongoing demand so that we can re-sell her if our plans should change a few years from now.

So what do you think? Do you have boats you suggest we should consider (and why)? How about anything on the market now we should consider? Any high-quality, under the radar type of boats I might be missing in our particular search? What might be helpful is something like: "Look at XYZ boat in the 1998 range. They are under-appreciated boats that might fit your criteria."

[monte]

Great question KIT. Really well thought out and specific (without being too specific) addressing your own needs. Hopefully other buyers will use it as a pro forma for asking similar questions. Preferred basic design criteria, cruising aims, performance, budget, location etc. and hopefully the answers won't be too far off your preferences (such as, oh you should buy a catamaran!) it's really sensible not to consider just one design you have come across as being the best, and instead consider quite a few different designs that open up your choice of yacht as well as chances of picking up a good deal. Anyway I can't suggest a particular yacht, I just wanted to congratulate you on an excellent post and hopefully other members can suggest some designs within your criteria.
Cheers

[Shanachie]

That's a big boat for the Keys and Gulf Coast.

Draft should be 5 feet or preferably less for the Keys and not much more for the Gulf.

Air draft of more than 55 causes occasional problems. 65 or more causes major headaches.

Pick a boat starting from there.

[KeepInTune]

Any more input? I'd appreciate your thoughts and direction.

[Shanachie]

Originally Posted by KeepInTune

Any more input? I'd appreciate your thoughts and direction.

No one can pick your boat but you. You have to see a sailboat and say, wow, that's the one.

But resist the idea that bigger is better, especially where you want to sail. The ideal boat in the Keys has about a four-foot draft so you can get into all of the good anchorages on the bay side and also get through the shoal channels.

The Gulf Coast, where I now sail, has all kinds of shallow water. Many of the inlets are not passable with anything but shoal draft.

Consider looking for the smallest high-quality boat that will make you happy. Personally, I think something like a Bristol 35.5 with a centerboard would be a good choice, but it's one of many that would fit the bill.

[Red Sky]

You will not sail at 8-9 knots with the size boat you are considering.