SW Florida Boat Choices/Advice
I sailed out of Sarasota for a number of years in the 1970''s and still sail down there with my father when I get a chance. You live in a really wonderful sailing area. Like the Chesapeake where I sail now, you are exposed to a wide range of wind conditions and the weather can change quickly. The predominant late spring, summer and fall winds are quite light, punctuated by quick moving squall lines and lots of short chop.
Shoal draft really is important down there, as a boat without shoal draft is excluded from mnany of not most of the best cruising spots. In many ways, the west coast of Florida and keel-centerboard boats were made for each other. Properly modeled K/Cb boats offer the best combination of windward and leeward performance that can be achieved short of a full blown deel fin keel.
I am not a fan of a wing keels for that shallow a venue. Wing keels work reasonably well when you can get a reasonable span to the keel foil. When you talk about a 36 foot wing keel boat with even moderate displacement, the foil span gets so short that a wing keel is a serious compromize in performance. I found that I spent a lot of time beating up narrow cuts when I lived down there, and frankly, personally, I would consider a wing keel an unacceptable choice for a 36 footer with a less than 5 foot draft in that venue. I also think that a wing keel boat is a bad choice for that sailing area because there isn''t enough tidal range to assure you of getting off in a bad grounding.
The problem as I see it is that Keel/Centerboarders began to fade out of popularity by the early 1970''s when racing rules pretty much wiped out any rating advantage and tastes seemed to have changed. That said there were still some decent K/Cb''ers made well into the late 1980''s.
In many ways a 40 foot trimarran, like the Condor would be an ideal boat down there with their shoal draft and excellent all around performance. Unfortunately most would be outside your range.
I had previously put part of this list of candidates (albeit less expensive and older) together for Duane and have added a few that are more in keeping with your budget:
Probably my first choice in this size range and price range would be a 1970''s era Tartan 34. These boats offer a lot of well rounded characteristics, being well built and nicely detailed. There are lots of well maintained examples up here on the Chesapeake that come available in your general price range. (The later 1980''s era Tartan 34''s were also really neat boats but the shoal versions had a wing keel I believe)
Probably second on my list would be a number of different sized early Sabre''s that should be available in your general price range with a keel/centerboard.
The Pearson 323 has always struck me as shippy little boat. I''ve never sailed one, but I have always liked their looks. They would not be great performers by any fair measure but would be reasonably good boats for what you have in mind.
I like the Tartan 3000 (or the earlier Tartan 30) both seem to be very good boats. A good friend (who was new to sailing at the time) bought a Tartan 31 about 3 years ago and I have been exceedingly impressed with that boat''s performance and capabilities. He and his wife have done some pretty ambitious sailing in the three years he has owned her.
Other posible options:
Bristol 35.5 Sloop: These were available with several keel configurations but the K/cb versions sail well and are nicely built boats. The ones in your price range may not have the higher quality construction that Bristol later became well known for in the late 1970''s and early 1980''s.
Cal 34, 35, 36: (1960''s)
Of the three I like the 36 best and then the 34. These are not terribly robust boats but are very reasonable for what you have in mind.
C&C 34 and 35: Of the two the early 1980''s 34 had a better layout, construction and were
offered as Keel/centerboard boats. These are a bit more on the performance side of this list but are still good boats. They are a little short on ventilation.
C&C 37: (early 1980''s) These were very nice boats in a lot of ways. Like many of the C&Cs'' they are a little short of ventilation but they had a nice layout and good performance. At 4''7" draft the Keel/cb version would be a very good choice for your area.
Ericson Independence 31: These are not very well known boats but were essentially built for precisely what you have in mind. They too are a little short on ventilation.
Ericson 35: I have a fair amount of experience with these boats. They are a little deep and are nothing super but in thier day they offered a lot of performance and a reasonable build quality.
These were real pioneers in fiberglass construction. While not well known today, these were super boats in thier day. You can buy them pretty inexpensively in really nice condition (look on Yachtworld at Pegasis up here on the Chesapeake)
Morgan 35, and Morgan 34 (not Out Island series boats): The Morgan 35 is a new design and offers better performance but of the two the 34 has always appealed to me more. While not a high performance boat on any objective standard, these were really good sailing boats. I have sailed them in a range of conditions and generally been quite pleased with them overall.
Pearson 35: These were real basic lets go sailing kind of boats. They offered good sailing characteristics and reasonable build quality but not super performance. They have a great cockpit, but that comes at the price of a small cabin area. Still these keel/centerboard boats might be just the ticket for poking around the backwashes of your chosen region.