Typically they change the wines from tasting to tasting. On one trip we did all four sessions and overlapped three or four. Not really bad considering we sampled 24 total.
If you are really into the process, you might chat with one of the Cellar Masters (the crew members who lead the tasting) to let them know you will be repeating. As they are expertsand judging by their passion it is as much of an art as it is a job, they always seemed happy to mix things up with the selections. (Keep asking for an Ice Wine!)
The information is always basically the same (as many guests are first-timers and just having funwhich, with all due respect to the one or two wine-snobs in the audience who like to show how knowledgeable they are by grousing at the simplicity of the presentationis the point!) but the insights to the vineyard, grapes, etc. is different. Again, this is true as well if they know you are a return taster with an interest in the details.
Without being too glib about the wine connoisseurs, this is a great opportunity to try different wines and learn a little about the differences in types, origins, grapes, etc. Sadly, the whole wine thing can be so unnecessarily complex that many people simply avoid the awkwardness of making a selection. (Ever have the experience of an impatient waiter standing over you at a restaurant as you scan over a wine list with unfamiliar names and a spectrum of prices. . .9 times out of 10 he knows less than you do!)
The point is to find a wine that tastes goodor hopefully greatto you. Period. The truly exceptional thing about these tastings is that the Disney crew goes out of their way to take the mystique out of the process and equip you with the ability to find something you can enjoy both on the ship and back home. (And hopefully learn there is not a thing wrong with going into your local wine store an asking for Something good that goes with *fill in the blank* and costs less than $10!)
If you have ever been even remotely curious about wine, this is a must do on your cruise. And for those seasoned experts who are inclined to become exacerbated by introductory level discussions, just try to avoid pulling a Paul Giamatti from Sideways and beating on the tables screaming I wont drink any &*%$#@! Merlot!