It sounds like you want a boat that will come down the East Coast via the Barge Canal & Hudson River, you''ll be leaving from Florida in the late Fall for the Bahamas, and then wind your way down to the Virgins using the many techniques and solid recommendations of Bruce VanSant in his _Passages South_. And at that point, you''ll want your boat capable of taking you down to Trinidad, or perhaps across the Central Caribbean to see Guatemala, the Honduran islands, and Belize.
Your boat will be quite basic by today''s standards (meaning it can be comfortable, safe and well equipped to motor, sail and anchor
...but forget about most of the trappings you see in the CW interior shots). You''ll have the ideal size to make cruising less work and more fun than it will be for most of the other cruisers you meet along the way. It most likely will not be a stock boat as we refer to them here, but rather one that has already been upgraded some and been to a few places. Why? Because good solid cruising boats have usually been cruising, because you''ll conclude while doing your research that a lot of money and time can be poured into turning a stock boat into a well set-up cruising boat (which your stated budget does not allow for), and because there will *always* be custom touches and special gear any new owner will add, so what leftover cash and time you''ll have will still be needed. AND because the best thing you can be doing with your boat is sailing it, anchoring it, weekending on it, and generally building skills and an understanding of what you need (vs. what you want - and not tearing it all apart and rebuilding it.
Your boat will be affordable for you because you can find great cruising boats in your price range. Good candiates will seem "small" if you''ve oogled at Hunters and Catalinas at the boat shows, because your perceptions have been calibrated to a bubble-boat design that has tons of beam, lots of hull freeboard, and scant underbody when, in reality, you''ll want more storage room, a simple/functional layout with at least one good sea berth, and a decent place to store the inflatable upside down on deck.
This probably sounds very vague since I''m not whipping off lots of boat designs, but in reality your task is to develop a good sense for what YOU think is important to find on the boat you''re looking for, and that has little to do with specific boat models that were built 20 years ago in a stock configuration. But just to finish up with a few examples, here are three for you to mull on:
1. Albin Ballad 30 - for sale recently on the Great Lakes in superb condition; routinely used for North Sea sailing by Scandanavians - very strong yet light and responsive. Functional simple interior, diesel equipped, and dirt cheap. No one up there seemed to know about it, and it was on the market for a long time.
2. Hallberg Rassy Monsun 31 - an Olle Enderlein design that''s been all over the world. Functional layout, diesel inboard, wonderful sailing boat, simple by today''s standards. (Two good books for you are John Neal''s Log of the Mahina and Mahina Tiare: Pacific Passages, the latter describing a Pacific cruise on a Monsun and both books offering an Appendix on setting up a basic offshore boat). One was recently for sale up your way with a Monitor vane, good stout anchoring gear, and again was very affordable.
3. The Irwin 30 that''s just down the dock from us. (My tonque is in my cheek on this one, since I''m in St. Pete, FL...but read on). Irwins, built in St. Pete, FL, usually were good sailing boats but built poorly/cheaply. The one I''m talking about is a perfect example of the boat I described in the above paragraphs: totally rebuilt by the owner with cruising in mind, now with a small bowsprit, expanded sail plan, fresh paint
, functional cockpit and new engine, and he''s finishing up the interior as I write this. And then...he''ll sell it. Has big boat fever and is anchored in a job, seeing himself for now as a liveaboard, not a cruiser. There are boats like this all over the world, and certainly up on the Great Lakes. Your job is to ferret them out...which can be great fun.
Good luck on the search.