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We've traveled during Thanksgiving the past 3 years, once to Mexico, once (this past Fall) to the Dominican Republic, once to Jamaica. Our kids are a little older (oldest is now 18), so I can't address the room issue (we just got rooms nearby, which worked fine for us).
However, in regard to weather. Weather can be constantly changing, but here's our experience. Mexico was warm (low to mid 70's during the day), but cool once the sun went down - we were covering with our towels by 5:30pm when the sun went behind the buildings. We needed sweaters in the evening and air conditioned restaurants are unnecessary. Pools were cool - chilly getting to the swim-up bar, ok as long as you stayed in the sun, but cool otherwise. Ocean was too cool to remain in for long. This is coming from someone from Maine who has a hard time getting into our ocean at all in the summer!
Weather this past Fall in DR (La Romana on the southern side) and Jamaica (we rented a villa 1 hr from Montego Bay) was great - high 70's during the day, ocean and pools comfortable to stay in all day. Just being a little bit further south helped. Sunset the same time, and needed a sweater in the evening.
Hope this helps. It's fun traveling Thanksgiving week. The kids only miss 2 days of school (for us), and it's off-season for the rest of the world, so the prices reflect that.
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