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First, be sure it is legal to ship plants to the destination you have in mind. Some states have strict rules regarding import and export of plant matter, to try to keep invasive species from ruining natural habitats. In many cases, import/export laws and customs delays make it impractical to ship live plants across national borders.
Next, check the weather at the destination and along the route. If your plants will be harmed by freezing temperatures, make sure they won't pass through a cold zone.
When shipping a load of live plants, be aware that any such shipment is vulnerable to inspection by the U.S. Department of Agriculture, which could hold up the load by a day or more.
If sending live plants via UPS or another standard carrier, try to send them on a Monday so that they won't run the risk of sitting neglected over a weekend.