You will be sending to my PO Box, which means your watch is in the hands of the postal service until I personally pick it up. When I send it back to you, I will take it personally to the post office. To get this security, you must ship your watch USPS. Do not ship to me using UPS or FedEx. They do unpredictable things when faced with a PO Box address.
USPS's Priority Mail boxes are free, and quite suitable. They are good quality boxes, and insurance protection is affordable. Priority service is fast and reliable.
If you are shipping a modern wrist watch that has shock protection (anything made after approximately 1960, or is marked "shockproof" or "incabloc" or "diashock" or similar) it is pretty safe to send in the small fixed rate box (the one the size of a VHS tape). I recommend placing the watch in a sealed plastic bag like a ziploc, wrapping the bag around it, and then adding bubble wrap to keep the watch in the center of the box.
Wrap in several steps, taping with scotch tape periodically. If there aren't several sealed and secured layers, it's easy for the watch to work its way out of the bubble wrap and to the corner of the box, where it has no protection. Your goal is to tape up a bundle that keeps the watch in the center.
Styrofoam peanuts offer no protection at all, because they do not hold the watch in the center of the box. Do not use them. If you have no supplies at all, packing well with newsprint, with the goal in mind of keeping the watch in the center of the box, can work. Again, tape up a bundle.
If you are sending a pocket watch, or any wristwatch that you do not know for sure is shockproof, do not use the small flat rate box! It is only 1.5 inches thick, which is not nearly thick enough to provide any shock protection from the front and back.
For sending one pocket watch, I prefer to use the 7x7x6 inch Priority Mail box. This is not a flat rate box, and you have to ask for it specially at the counter, or order them (free) from the USPS site. Otherwise, the medium flat rate box is fine, but the 11 inch length is a little long. If you make a bubble wrap bundle with your watch in the center, and place it in the center of the box, you can use newsprint to fill in the two ends.
When your watch is packed, send it to me with adequate insurance coverage.
If you want insurance more than about $800, you will find that sending it Registered Mail will save you money. This is a very secure mail service, where the box is sealed in a special way (you must use brown paper tape, which is marked all over with a stamp to make any tampering evident) and then each person who handles the box signs for it. You can still use the Priority boxes, and if you don't have the right tape the employee at the counter will seal the box for you. Be aware that this service is very safe, but it can take weeks instead of days.
The Time Guy
PO Box 84726
Lincoln, NE 68501-4726
Because this is a PO Box, use only USPS when shipping to me. Do not use UPS or FedEx. When you have shipped your box, please email me the tracking number.