We always have fun doing a Monorail or Skyliner crawl!
On our Monorail crawl, we hit the Poly, Grand Floridian, Contemporary, Wilderness Lodge, and Ft. Wilderness. You can usually do it using just monorail and boats. I know the boats are a little more challenging right now, but I believe you can still take a ferry from WL/MK and FW/MK.
On our Skyliner crawl, you can hit Yacht Club, Beach Club, Boardwalk, Riviera, Caribbean Beach, Pop and AoA.
We hop around to the different bars/lounges and grab drinks/snacks unique to each hotel. And is especially fun during the holidays when you can check out all of the resort decorations!
You could start/end at Disney Springs by taking a bus to/from the first/last resort. And we always enjoy the Christmas Tree Trail in Disney Springs during the holidays! (I'm not 100% sure if they're still doing that this year?)