Most gas and fuel cans sold today do not have a vent hole and have spring loaded nozzle spouts. (I guess for safety reasons). Blitz is a common brand. I've filled them, put the nozzle on and had them tip over in back of the truck and never lose a drop. They are OK but can be a hassle if you have to support the 5 gallon jug while filling a tank. It will fill slowly then stop and suck air back through the nozzle so the next half gallon can flow into the tank.
I fill my 5 gallon cans at the gas station (red cans for gas, yellow for diesel, Clear or blue for kerosene). In my area you must use these type safety cans, If I show up with something else they won't let me fill them.
Once home I pour the diesel into a 15 gallon white (opaque) container using a funnel. That container sits on a 4 wheel dolly I can roll over to the tractor and fill the fuel tank using a universal 12V electric fuel pump that runs off a 12V trailer battery.
You can always opt for a fuel caddy but I think they are expensive. Northern tool has several but the ones with a hand cranked pump are $400 and up. Of course the gravity feed ones must be higher than what you are filling.