There's plenty of room for personal opinion on this one, but I'll give it a try. I imagine some other Forum members will want to offer their own suggestions.
I ought to start by confessing that I haven't built many wood kits. I tend to lean toward either plastic kits or scratchbuilding. But I think I'm reasonably familiar with what's out there.
If you're an experienced plastic modeler I assume you're interested, at least to some extent, in the concept of scale modeling - that is, building reasonably accurate replicas of real ships. If that's the case, the list of manufacturers that offer suitable kits is actually pretty short.
One British company, CalderCraft (also known as Jotika) and three American ones, Bluejacket, Model Shipways, and A.J. Fisher, sell wood kits that are designed by people who know what they're doing to produce genuine scale models. Unfortunately the wood ship kit industry also contains several continental European companies who sell "plank-on-bulkhead" kits that have something (I'm not sure what) other than scale fidelity at the top of their agendas. Caveat: the kits from those companies (Corel, Amati, Artesania Latina, Mamoli, Euromodel, etc.) do vary considerably in quality; I'm sure some are much better than others. But I have yet to encounter a kit from any of those firms that I'd consider worth taking home from the hobby shop - especially in view of the outrageous prices they bring.
I've never built a Calder kit - or even seen one in the flesh. On the basis of the published reviews and ads, though, it's clear that this is a company that knows what it's doing. Calder makes plank-on-bulkhead British warship kits that clearly are designed to make real scale models. They have two big drawbacks, unfortunately: scarcity and price. The Calder 1/72-scale H.M.S. Victory, for instance, costs about $1,000. The lesser ships in the range are cheaper, but I'd be reluctant to suggest a Calder kit as a first effort.
A.J. Fisher is an old, old American firm with a fine reputation for solid-hull sailing vessel kits. The company has been dormant for quite a few years, but is now, under new ownership, coming back to life. At the moment it only offers a couple of kits, but I'm confident that they're good ones.
The two big American competitors are Bluejacket ( www.bluejacketinc.com ) and Model Shipways (distributed by Model Expo: www.modelexpoonline.com ). Both offer a wide variety of kits in both the solid-hull and plank-on-bulkhead formats.
You may want to start by making up your mind whether you'd prefer to go the solid-hull or plank-on-bulkhead route. Generally speaking the former will produce a nice model faster - especially in the case of a relatively large ship. But the plank-on-bulkhead format has a lot to recommend it as well. In that sort of kit you feel like you're building the actual ship or boat more-or-less like the real thing was built. And both companies offer nice plank-on-bulkhead (or plank-on-frame) renditions of small vessels that don't require an enormous investment of time.
The big piece of advice I usually offer is: start with a relatively small ship or boat on a relatively large scale. Too many people dive into the deep end of the hobby with both feet, starting with a Constitution or a Flying Cloud. Most of those folks never finish their first models - and most leave the hobby in frustration. The learning curves in ship modeling tend to be short but steep. To build a big Constitution takes several years. Six months into the project, the typical modeler gets dissatisfied with the work he or she did at the beginning. Rather than tearing things apart and starting over in those circumstances, it makes far more sense to invest one's time and effort in a smaller, simpler model. Any sailor knows that many small ships and boats have their own subtle beauty and character. A well-executed model of a sloop or a schooner, or for that matter a catboat or a dory, makes a fine mantle decoration. And the month or two that went into its construction will be of huge value to the builder when he does tackle the ship-of-the-line or clipper that he really wants.
Specifically - in the plank-on-bulkhead category, Bluejacket offers a couple of large scale dories, a catboat, a lobster boat, and several other small craft that would be great starter kits. Moving up the ladder in terms of size (and down it in terms of scale), the same firm's pilot schooner Mary Taylor and fishing schooner We're Here (a fictitious ship, based on the one in the movie "Captains Courageous") are good solid-hull starter ships. The Model Shipways plank-on-frame skipjack Willie L. Bennett is a beauty - though some of the woodwork in the early stages is kind of challenging. The MS solid-hull pilot schooner Phantom, colonial schooner Sultana, revenue cutter Harriet Lane, and privateer schooner Dapper Tom also would be good choices. (Warning: when you check out the Model Expo website you'll promptly discover that many of the Model Shipways kits are out of stock at the moment. The company is in the process of re-introducing several solid-hull kits that have been off the market for several years, and apparently there's been some sort of glitch in the production process.) I believe MS offers the Phantom and Sultana in "everything you need" kits, including tools, paint, and a copy of George Campbell's excellent book, The Neophyte Shipmodeler's Jackstay. One of those would be great to start with.
Those are personal opinions, but I hope they help a little. Good luck. It's a great hobby.