You cannot drive from Alaska to Colorado with an animal that needs CITES papers from the US to get into Canada and CITES papers from Canada to get out. It is not feasible.
If Delta will take him that's an option. They are one of the better airlines to ship with. Continental is also very good. They might be prohibitively expensive though. You can put a Ship Your Reptile box inside a cheap dog crate but make sure the LIVE ANIMAL labels are on it. You can also speak to the person who greets you as you board the plane and explain you are worried about him. They are very understanding and will call down to the ground crew and keep checking and will let you know when the animal is safely stowed. It never hurts to have the steward or captain call down and ask the ground crew. They've even let me down on the tarmac to check on animals.
I would ship in a deli cup with a stick securely fastened (through the deli cup) at about a 45 degree angle. He will hold on to the thin branch very securely. Pack a moist paper towel at the bottom. I just received an adult gracilior female packed in a bag and I didn't like it. I thought it must have been very stressful for her even though she was perfectly safe. She was in a bag with a lot of packing peanuts around. I thought she might have felt as if she was in the clutch of a predator the whole trip.
You have to ship through an approved shipper such as Ship Your Reptiles.
Call them for advice. You can buy all the supplies from them. A bigger container isn't better as he'll have further to bang around if the box is dropped. I would recommend you buy P22 packs from Ship Your Reptiles. They hold the temperature at a constant 72F (22C). They do that by releasing or capturing energy (heat) as they change from a solid to a liquid or liquid to solid. Since you are leaving from Alaska, I would put quite a few in, melt them and get them fairly warm.
I would also recommend you ship before you leave. It is not all that easy to get them in the box--you need a bit of experience for that. I am sure you could ship to either a vet's clinic or someone from this Forum. If you were coming to my city, I would be happy to pick him up from the ship center and hold him for you. I'm sure there are lots of people who wouldn't mind helping you out.
Good luck, I know how stressful it is.