Well, my suggestions are going to be a little different from those that have been offered so far. In my opinion the best way to get into sailing ship modeling is with a relatively small ship in a relatively large scale. The aspect of the hobby that provides the most frustration is surely rigging. (That, really, is what makes a plastic sailing ship so different from any other kind of plastic model.) The smaller the scale, and the bigger the ship, the more challenging the rigging is going to be. On that basis, a big Victory or Constitution is most emphatically not a good newcomer's project - and a small-scale Victory or Constitution is worse. I've known of dozens, if not hundreds, of cases in which modelers new to sailing ships have started with such a kit. One of two things usually happens. One - the modeler gets overwhelmed by the complexity of the project early in the proceedings and gives up. Two - the modeler slogs away at the model for several months, and then suddenly discovers that the quality of his workmanship, and his standards of what's acceptable, have gone way up during that time. So the work he did three months ago no longer satisfies him, and he abandons the project.
My strong recommendation (which almost everybody to whom I've offered this advice has, of course, ignored) is to start with a project that doesn't take long. I say it makes more sense to spend a little money and a few weeks on a nice model of a small ship, as a learning exercise (which also, incidentally, will produce a mighty impressive display for the family mantle), than to sink several hundred dollars into a huge kit that will never get finished.
I enthusiastically second Jim's recommendation of the old Pyro fishing schooner Gertrude L. Thebaud. (It's an old kit, but a basically sound one; it's appeared at various times under the Lifelike and Lindberg labels - sometimes under the slightly deceptive name "American Cup Racer." But it's unmistakably a fishing schooner, and it makes a beautiful model.) At about the same time (the early fifties) Pyro released a model of the American revenue cutter Roger B. Taney. (It's also appeared in Lifelike and Lindberg boxes, labeled "Independence War Schooner." Another old Pyro/Lifelike/Lindberg kit that's started quite a few modelers out in the sailing ship (or, in this case, sort-of-sailing ship) genre is the revenue cutter Harriet Lane (aka "Civil War Blockade Runner.")
Taking off in a completely different direction, I can recommend three kits that represent ships from much earlier periods and that would make fine newcomer's projects: the Viking ships from Revell and Emhar and the medieval cog marketed by Revell and Zvezda (same kit). I built the Revell Viking ship a couple of years ago, and I'm extremely happy with it; though the instructions don't tell you so, it is in fact an extremely accurate model of the Gokstad Ship, one of the two major surviving Norse vessels. I was almost done with that model when the Emhar kit was released. In some ways it's superior to the Revell one (they both represent the Gokstad Ship), and Emhar also offers a couple of sets of figures to populate the finished model. I haven't built the Revell/Zvezda cog, but it's gotten generally favorable reviews. The price is kind of steep for what you get, but it strikes me as a near-ideal introduction to sailing ship modeling: one mast (plus a bowsprit) and just enough rigging to provide a sound working familiarity with the subject without involving much repetition. And what a lovely model could be built from that kit.
Hope all that provides at least a little food for thought. Good luck. It's a great hobby.