I could be wrong but in my opinion it might cost more to build, store and drag a worthy vessel behind a truck that you couldn't afford the fuel for to be able to drive it around every day. i would check into a hauling company find out the rates and figure out about how many times you might move the vessel and do the math to see if it is really worth it to buy a boat just for the ability to move it yourself. just my .02 but i would go for a better boat and have it moved that way it will be insured while it is moving and it will have a professional driver that knows each states laws.
We just bought a Watkins 25. We really like her. We just brought her down from Jacksonville through some nasty weather on the ICW and she handled it well. I would take her to the Bahamas in a heartbeat.
Most are listed under $20,000. The each were individually build to the owners specs, so each is a little different. Lots of room for a small boat. She has 5'11' headroom, sleeps 5, 2 burner alcohol stove (we are replacing with a safer, newer one), large icebox, sink, enclosed head,(some have marine heads) ours has a porta-potti, sink and shower head. Here are a few pictures of her. http://www.sailnet.com/photogallery/showgallery.php/cat/624
She looks and sounds just great!!I hope you have many years of fun in her and with that draft you can tuck into the best places.
May I suggest when you cross to the Bahamas ride the stream from Angelfish Creek to Bimini.
Clipper Marine 32. Trailerable without permits (8' beam), roomy, aft cabin, oputboard powered, and cheap. not the world's greatest sailer, definitely not a bluewater boat, but good bang for your buck. Good ones can be had for well under 15k, trailer included.
An old friend lived in an ODay 25 in Homer, Alaska. He worked two weeks on - two weeks off - on the north slope - so he was on the boat for two weeks at a time - in Homer, Alaska. It was the simple life. I met him wilst skydiving in Anchorage, Alaska.
And what's wrong with a few night skydives. I've got about a dozen. There is nothing like a good full moon in free fall...
You might also look into a Cascade 29'. Mine has 6'3'' head room and plenty of space and a nice galley. I've been living on her for 2 years never had a problem. The V-berth did have a door but i removed it for ease of life but put it back on some times for more privacy. Also the hulls are bullet proof 7 layer layup of awesomeness so thats another route you could go
Columbia made a trailer-able 26 ... i have the fixed keel model built from 1969 to 1976
possibly the largest below decks 26 I've been aboard ... and at 6'4" headroom was a big concern points well sloop rig easy to single hand especially if you add a furling head-sail and halyards to cockpit.She takes big wind (have sailed in 40 + mph) for her size. She is heavy 7000 lbs dry and empty. the outboard is mounted in a well originally but many guys went to transom mount which is fine except in a heavy following sea. can be used for live a board but would need to add grey water and black water holding tanks.
S/V Aline SV-Aline
I've lived on a Paceship PY 26 (fin keel/4.5 draft) for almost 2 years now. It's fine for 1 person, but a couple would be cramped. The Paceship Website Homepage has all the specs
The Centerboard model is probably better for trailering, mine needs a tractor trailer.
-6 ft. headroom
PY 26 has 6'1" except at door headers, cabin area is roughly 7x7.5'
-26 or 27 ft. (as far as I know, the max. length that still qualifies as trailerable)
Trailerable = gross combined weight, pickups are limited to 2-3000 lbs. gross combined weight, a tractor/lg. car carrier type truck would be needed to stay legal.
26' 6" x 9.5' beam (needs wide load signs) and 6400 lbs. empty, I'm around 7200+ lbs. now.
-outboard engine (avoid hassles of inboard)
I have the outboard option and it gave me room for a 45 gal. fresh water holding tank and other misc. storage where the inboard would have been. I'm currently moving my 3 batteries up front behind the head holding tank (under V-Berth) to help balance the extra 370 or so lbs. of water under the cockpit. I also have a fume sniffer (propane/butane/gasoline/sulfuric acid etc.) going.
Head w/ holding tank and I also added a shower w/ elec. pump.
-at least one berth with a door: fore or aft, doesn't matter which
Cockpit> Cabin > (door) private head > (door) V-Berth w/ small stand up changing area.
I heated it w/ a 4-8k btu Propane space heater and it was 72F+ inside w/ 0-10F outside winter temps in Rhode Island. I also insulated it w/ the foil over bubble wrap flex. insulation.