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We are allowing shipping to multiple addresses during checkout for guest customers. The steps are a lot simpler for an existing user since we can pull addresses from their account for them to choose.
However, guest customers have to do the following for every address:
What are some good examples you have seen in the past? What are some considerations to look out for?
It's not the answer you want perhaps but the simplest way to solve this is to simply tell users that if they want to ship to multiple addresses, they need to register. Guests can ship to one address.
If it's that important to them, they'll do it. And it's not that great of a barrier to entry, unless shipping to multiple addresses is extremely common.
And it's not that uncommon for guest accounts to be limited in some way, so it should not surprise anyone to be told this limitation.
Not every User Experience problem can or should be solved with User Interfaces.
