A million Thank Yous @GatorsFan for removing a thorn in my side, or more like a thorn in my eye. 2) is the solution I've been searching for to be happy with my Garmin Drive 53. It's just old enough to not have built in wifi, but does have a micro sd slot. The only official way to update this thing is with Garmin Express. I'm a Linux only user, and have wasted countless hours with Virtualbox as well as actual PCs of various makes and models, using various flavors of Win7 thru Win10 trying to update this thing with no success. I managed to get it to update one time when I first bought it using my wife's Win10 PC, but ever since then Garmin wants to update the software on her machine before proceeding, which I was reluctant to do. I had resigned myself to using it as it was without updates because I like the device.I have a Garmin Nuvi 50 GPS - there is no way to my knowledge to get Garmin Express to work correctly on Linux with or without WINE - you have two options
1) run Windows from a virtualbox
2) use the map data from https://www.openmapchest.org/
for Wine issues see here - https://forum.winehq.org/viewtopic.php?t=37739
Your solution #2 works perfectly, and I prefer OpenStreetMaps anyway. I would highly recommend to other Garmin users to try this and give up on the official updates if you can.
Oh hey, are you also a Tom Petty fan?

