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Key Dates for Holiday Planning

Nov. 27: First night of Chanukah.

The first night of Chanukah this year is Nov. 27. If you give gifts or host dinner, you'll clearly want to jump on any shopping you need to do as soon as possible. The last night of Chanukah is Dec. 5, though, and you could get a lot of great gift deals on Black Friday. If you buy anything online on Cyber Monday, however, you may need to pay extra for rush shipping, as you'll see below.

Nov. 28: Thanksgiving.

In the U.S., the kickoff to holiday shopping typically happens the day after Thanksgiving—although holiday creep has been pushing some mega-sales to the day of Thanksgiving. Seeing as it's Nov. 28 this year, that leaves only 26 days until Christmas. Despite whether you celebrate Christmas, chances are the bulk of your holiday plans will occur between those two days: shopping, cocktail parties, annual work celebrations, other religious get-togethers.

Nov. 29: Black Friday.

In some stores, Black Friday will actually start late Thursday night, though some will still wait until midnight or early Friday morning to open their doors. This is the day to get trampled by crowds for the lowest prices on in-store purchases. If you have your eye on a product that might be discounted—which usually include a lot of hot technology products such as HDTVs, laptops, desktop computers and monitors, smartphones and tablets, and cameras—you'll probably get the best price of the whole year on Black Friday.

Anti-consumerists who hate Black Friday can rest easy knowing that Nov. 29 is also officially Buy Nothing Day in the U.S. (it's Saturday, Nov. 30 in the U.K. and other countries this year).

Dec. 1: Cyber Monday. Dec.

1 is a great date to shop online for a few reasons. First, you'll often find the biggest online discounts on this date. Second, this year Cyber Monday falls late enough on the calendar that, given the standard 30-day return/exchange policy, gift recipients have a little extra time on their side if they need to change the item.

Dec. 2: First Tuesday of December.

The first Monday and Tuesday in December are both typically sales-driven days. This year, the first Monday of course is the same as Cyber Monday (the Monday after Thanksgiving), but don't dismiss Tuesday as a great day for deals both in brick-and-mortar stores and online. If you're thinking about taking a day off work to get some shopping done, Dec. 2 might be an ideal day when crowds won't be as thick, and you still have a good chunk of time on your side.

Dec. 5: Last night of Chanukah.

While it's certainly not official, I'd bet that the last night of Chanukah, which falls on a Thursday, will this year mark the start of holiday party season. If you're hosting a get-together, you should have a clear game plan in place by now for your event. If you're attending, you might want to mark this date on your calendar as the cutoff for buying gifts for the hosts.

Dec. 9: Green Monday.

eBay apparently coined the term "green Monday" as the company's most profitable day of the year. ComScore refers to it as the Monday in December with at least 10 days before Christmas. In any event, you won't get bargain-basement deals on this day, but you might see some more modest deals. I think of this date as when organization ends and frenzied shopping begins. My goal this year will be to get as much shopping done as possible no later than Dec. 9.

Dec. 17: Order Cutoff for Amazon Free Shipping (except for Prime subscribers).

Amazon shoppers should note Dec. 17 as the last day to get free shipping and a guaranteed pre-Christmas delivery date. Amazon Prime subscribers ($80 per year) get two-day free shipping on all purchases, so their cutoff date is a few days later.

Dec. 21: Order Cutoff for Amazon Two-Day Shipping.

Dec. 21 is the last date that Amazon offers guaranteed pre-Christmas delivery for two-day shipping, which is free for Prime members and costs a bit extra for everyone else. You can still pay for one-day shipping on Dec. 23, or get local express delivery on Dec. 24, but it's probably not an ideal situation for anyone.