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@Mrs. Lemon-Lime: I have an office but have pumped and traveled with milk.

I would suggest a good cooler with hard plastic sides (fabric coolers leak as ice melts). If you have a good bucket of ice (think 1-2 containers of a hotel room ice bucket) you should be fine for the day. Remember technically BM can be left at room temp for 3-6 hours.

I have pumped in a parking lot. In the back seat is obviously more private than up front. But front seat isn't impossible especially if you have a cover.

I am not sure what "pump systems" means. I had a freestyle and loved it.

My freestyle came with a small cooler. My routine for pumping at work is to go out to my car, remove my uniform top, put cover on, unsnap tank top, attach pump flanges, pump, undue all previous parts. I usually leave my bottled milk in the cooler in the car, with my pump parts in the cooler too.

I have pumped while driving, no big deal. When I was finished, I just turned the pump off. Upon arriving at my destination, I unhooked everything and fixed my clothes before removing my cover.