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Ritz or JW in Cancun?
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I’d say North.... N Michigan (Mackinac Island is 8 hours), Apostle Islands, Door county, Wisconsin Dells for outside activities.
Petoskey/Harbor Springs/Traverse City/Glen Arbor/Leland
Lake Geneva maybe? Enough of a city to have fun. Door county I’ve heard is cute too
Walloon Lake, Michigan
Western Michigan - towns like Holland and the lake coast
SW Michigan probably for you... N Michigan and Apostle islands may be too rugged
This is outdoors but the land between the lakes is supposed to be cool. My family drove through on their way back on a road trip.
Saugatauck (I can’t spell) Michigan 100%. Super cute downtown on the water with cute restaurants and a little shopping, lots of wineries around, beach close by. 2ish hour drive from Chicago. Stay right downtown. Tons of places available on Airb&b
Hike at starved rock or Matteson state park. I usually do day trips, hike and then have dinner and drinks at the lone buffalo restaurant owned by tangled roots brewing