At that rate, learning about most regions and varietals is an expensive proposition!
But, it's fairly easy to find cheap-to-free ways to taste bunches of wines, and even be able to purchase them inexpensively (well... below list, at least). First, and foremost, find out if your local wine store has regular tastings, be it weekly, monthly, whatever. Sign up for their mailing list -- either email or postal, most stores offer one or both. That should keep you informed of both regular and special events (producer visits, new releases, etc). Generally, tastings are free or only nominally expensive -- in my area, there's 3 chains. One has weekly, free tastings of 6-8 wines per week, and offers coupons for 50¢ to $4 off per bottle for wines on the tasting (depending on the price of the wine). One has a once-monthly tasting of 30-40 wines that costs $10. One has quarterly tastings at each of it's locations (there are 4 within a 20-mile drive of my house), with 60-80 wines, also costing $10. Both of the $10 tastings also get you a $5 gift certificate for use the day of the tasting, so that's a possible rebate (and, in both cases, the gift certificate is for any wine, not just wines on the tasting).
All 3 stores also have email and postal mail lists, with the occasional producer or importer visiting and showing off their wines. Those tastings are free.
Now, there's also 4 wine bars within an easy drive of my house. 3 have enomatic machines (card-reader operated machines that store wine using argon to preserve it, and dispense wine at the touch of a button), while one is a traditional "pour from a bottle" bar. These aren't free -- it's usually $2 to $10 for a 1 oz tasting pour, but the wines are generally slightly pricier than those served in the wine shops (eg, one of the enomatics had a highly sought-after Napa cab -- Cakebread, which retails for around $100 -- for $12 in a tasting pour). Kind of a fun, build-your-own-tasting, and a really interesting option for having a night out with friends. We spent my last birthday at one of them, and for 6 people, spent about $100, which isn't all that much considering how much wine we got to taste.
Finally, many restaurants have tasting flights. It's usually noted on the bottom of the by-the-glass menu. Generally, it's 3 wines, in 2-3 oz pours, for around $10-$15. Not always the best stuff, but it's often themed, which can be interesting. Usually these fit well with the theme of the restaurant, or the staff will have recommendations -- for example, at the suggestion of our waitress at PF Chang's one afternoon, I paired a trio of off-dry whites (a blend from Washington, a German Gewürtztraminer, and a Loire Chenin Blanc) to go with an order of heavily spiced fish. Similarly, while at Legal Seafood, the waiter suggested I have a Loire trio to go with a lobster-and-shellfish platter. Both were very good pairings.
One thing to note, though, about tasting at a restaurant -- not all wines are available for retail sale, and not all wines are commonly found on retail shelves even if they are for sale. Some wineries engage in the consumer-unfriendly practice of "allocation," whereby most of the production is slated solely for restaurants, while a small portion goes to retailers; the most famous examples of this would be Rombauer's Chardonnay and Cakebread's wines (Chardonnay, Sauvignon Blanc, and Cabernet). It's not the case in all states -- some don't allow the practice -- but I know that in Florida and Texas, it's perfectly legal.
Finally, some restaurants have tasting nights, where you pay $5 to "hey, how much do you want to spend," to taste anywhere from 5 to... well, many wines. A good way to learn about these is your local newspaper's "events" page, restaurant mailing lists, and the website localwineevents.com.
So, with a minimum of trouble, I can go to taste anywhere from 50-100 wines in a month, and spend only $30 or $40 a month. And if I can do it, you can too.
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