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Where to go in January with almost 2 year old - no cookie cutter resorts!

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We (me, my husband, our will be 22 month old daughter, and my mother in law) are looking for a unique place to go in January. My MIL will be visiting from Australia and is a very seasoned traveler. My husband and I are former backpackers, but now that we have a little one, we're looking for something family friendly but still off the beaten path. It would be nice to go someplace with mild weather but definitely does not need to be hot. All of us love unique places where we can explore real local culture, food & wine, town or country, but are still looking for something affordable. Finding a cottage/apartment with 2 bedrooms in one spot for the week works best with a toddler, rather than bouncing around various hotels. We'd be flying from New York. No cookie cutter resorts please! We want to experience the real life of the place we go to :)

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