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Late February?
I know it's a long way off yet but for my retirement celebration we are planning on a few days at the end of February 2019 (Feb 25th - Mar 1st). What has everyone experienced in the way of crowds at that time? We will be coming in early Monday morning and leaving late Friday afternoon/evening. Going all out and staying at the Contemporary with the Magic Kingdom view. So excited, can't wait!!!
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We often visit in February or March. The first thing we usually look to see is when is Mardi Gras (it's 3/5/2019), when is President's Day (it's 2/18/2019), and when is the Daytona 500 (very likely to be 2/24/2019). So it seems to me if you are coming in Monday, 2/25 and leaving Friday, 3/1 - you are probably positioned as well as you can be for crowds in late February. Valentine's Day / President's Day weekend can get pretty busy, but you'll be a week removed from that. The one potential issue that you'd have to watch for is the Disney Princess's marathon weekend. If I were a guessing person, I'd say that is likely to be the Fr/Sa/Su (2/22-24) just before you would arrive, but that's not official at this time.
I'd say go for it, have a great time, and happy retirement!
BTW - by Disney standards, this is NOT that far away!