Calculating number of polygons needing to be crossed?

Your question is unclear.

If you mean you want to know how many parcels to cross to get to each well, then you can create a minimum spanning tree (least amount of line work to connect your well locations). Creating Minimum Spanning Tree based on street network using ArcGIS Desktop? is another GIS SE Q&A that has links to an Esri tool for creating the spanning tree. Then, use a spatial join, or a select by location to get the total count of polygons that cross your spanning tree. Of course, you will need to ensure your data use a projected coordinate reference system.

If you want to know from each individual parcels to every well then create centroids from your polygons and one at a time, include those into the spanning tree and repeat the join or selection.

If you want to visit each individual well once from each parcel then you should search SE for the travelling salesman problem. I believe QGIS can do that.