It's an excellent question, and a rather refreshing one. I'm glad somebody is thinking in terms of something other than a Constitution or a Victory as a first project.
My general suggestion to folks thinking about breaking into sailing ship modeling is: pick a relatively small ship on a relatively large scale. Sailing ship modeling holds two potential terrors for newcomers: delicacy and repetition. Contrary to what some people seem to think, bigger sailing ship models are easier to build than smaller ones. Take a look at the rigging on any of Donald McNarry's models (largest scale: 1/192) and you'll see what I mean. And perhaps the biggest enemy of the hobbyist is repetition. Rigging the lanyard for a pair of deadeyes is, if you haven't done it before, kind of tricky. Doing it fifty or sixty times (as you have to do on a scale model of H.M.S. Victory) is downright depressing. I always recommending starting with something other than a full-rigged ship. My strong recommendation is to pick something with fewer than three masts, preferably with a schooner or sloop rig, on a scale of 1/96 or larger.
Far too many modelers insist on starting with big, elaborate projects, asserting that, because they've built other types of models, they won't have any trouble doing a Victory or a Cutty Sark. Rarely, if ever, have I seen such a model built by a newcomer that satisfied even the modeler's own standards. As anybody who's ever worked in a hobby shop knows, the vast majority of those big kits never get finished. (A lot never even get started.) If the "newbies" who buy them would just be willing to invest a few weeks of their time, and a few dollars of their money, on one or two smaller, less time-consuming models, they'd derive far more enjoyment and satisfaction from the hobby. And in the process they'd acquire some beautiful models to put on their mantles. (A ship model doesn't need to be big or elaborate to be beautiful.)
Unfortunately, that advice is easy to give but hard to follow. The plastic sailing ship market, at the moment, is in horrible shape. None of the big manufacturers has produced a genuinely new sailing ship kit in at least twenty years. The few plastic sailing ship enthusiasts are getting by on kits that were first issued as long as 50 years ago. One used to be able to find a dozen or so kits that fit my definition of good newcomer's projects; now there are scarcely any.
That said, I don't have any trouble agreeing with any of the suggestions that have been offered earlier in this thread. (I do have some reservations about the Revell Bounty; it's not a bad kit for its age, but it's on a pretty small scale, and it's a full-rigged ship requiring quite a bit of repetition.) I think my first recommendations would be several of the old Pyro kits, which are now being sold under the Lindberg label. (More correctly, they can be found in hobby shops with Lindberg labels. As I understand it, Lindberg as a company is no longer manufacturing plastic kits; I hear the molds have been bought by a new company that plans to market the kits under the "Hawk" name. But the Lindberg versions seem to be fairly common still.) Lindberg is selling them under some silly names, but they're still the old Pyro kits from the early and mid-fifties. The Morris-class revenue cutter is being sold under the name "Independence War Schooner." The fishing schooner Gertrude L. Thebaud is labeled "America's Cup Defender." (Yeah - a Cup defender with two stacks of fishing dories on her deck. Right.) And the steam/sail revenue cutter Harriet Lane is labeled "Civil War Blockade Runner." (That one is more defensible. The Harriet Lane got captured by the Confederacy, and did run the blockade a few times.) Any of those would make a pretty good starter kit. But those molds are more than fifty years old now. I haven't looked inside any of those Lindberg boxes lately, but I suspect they have more than their share of problems with flash, poor fit, etc.
Here's a link to a Forum thread in which a newcomer tackled the old Pyro Thebaud. In my opinion this is a fine example of how a "newbie," armed with a basically sound kit, some basic research, and a little encouragement via the web, can produce a first-rate, beautiful model of an important ship: /forums/582090/ShowPost.aspx
One other kit hasn't been mentioned. I hesitate to recommend it without having seen it in person, but the relatively new "Hansa Cog," by the Russian company Zvezda, strikes me as a near-ideal first sailing ship kit. It's on a quite large scale (1/76), and, with its single square-rigged mast, offers the modeler the chance to learn all the basics of rigging with a bare minimum of repetition. As I understand it, the kit suffers from one big goof: the deck planks are laid lengthwise rather than athwartships. That's the sort of thing the newcomer probably would be able to either ignore or fix. The cog was an important vessel in the evolution of the ship, and a model of one would be extremely attractive. (The various 1/76 wargaming figures on the market would make a fine, colorful crew for it.) If I had to pick a starter kit for somebody wanting to break into the hobby, that probably would be it.