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I know this site is geared towards art shows but:

I have been asked to do a commission for someone. I would have to mail the painting to them. Any suggestions on the best ways to ship a stretched canvas?

It would be an acrylic painting either 20"x20" or 26"x26"

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here is a video i made for packing canvas

1 inch insulation(home depot)

packing tape....foamcore

Thanks!  From what I gathered mailing through the post office is cheaper. Do they have any restrictions? I'd hate to stand in line at the post office to be told that they can't/won't do it for whatever reason

I buy my boxes from Uline & I ship all my pieces through FedEx. You can buy the foam sheets & cut them to size from most hardware stores. The problem I ran into with using the USPS is they don't carry boxes the sizes of my larger artwork. For me with insurance added & requiring my customers to sign (so they can inspect the package for damage) it was cheaper through FedEx. I think UPS fell into 2nd on shipping cost. If you set up an account w/FedEx, & print your own labels you can get it all even cheaper. I'm not sure what your requirements are but my pieces are shipped with glass.
Good luck,
Mel

Good to know, thanks for the help. I wanted to get as much info as possible before trying to mail it. I figured I would have to do a little shopping around. I didn't think about getting the package signed which makes complete sense. I just received the offer and wasn't sure where to start. 

Shipping the painting doesn't seem as daunting of a task. 

Take it to one of the UPS or Fed-Ex stores and have them pack it and ship it. It'll cost a bit more, but it's a hassle you won't have to deal with, and considering the cost of the materials needed, it's worth it to have them do it for you.

FedEx Ground is cheapest, but FedEx will only insure artwork for $500 max no matter what is the stated value of the artwork.

I dumpster dive for all my shipping containers since they're FREE. Furniture stores, especially those selling refrigerators, are great for BIG boxes. Bruce R. is steering you right for that insulation. Don't buy R Board type with a fiberglass surface, though. Sometimes the insulation has an aluminum face and then there's the type with no face at all. Rigid packaging is best with no airspace throughout. You might want to pack the canvas inside a box (cardboard folded around it nicely) and then put the insulation around that and box it again. I double box everything. The finished box should be at least 6 inches wide. I can't remember, but I think UPS even requires 4 inches all around from the outside of the box to the artwork just incase a puncture occurs. Kinda overkill.

Barrie that's great advice. Nothing wrong with a good dumpster dive. I could see how fiberglass would be a bad idea.

I'm pretty sure I will be going with FedEx. I want to insure it and have signed delivery. Sounds like packaging could be a long task but I've seen the prices for "art boxes." I think I'll spend an afternoon watching Netflix and packaging this painting.

Y'all have been a great help. Thanks for all the inputs

If it were me I'd insure it no matter how well it's packaged. Insurance is cheap, especially if you can pass the cost along to the customer.

I have a contract drafted that states that the patron covers shipping and insurance fees.

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