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You touch a willing creature. The target gains a flying speed o f 60 feet for the duration. When the spell ends, the target falls if it is still aloft, unless it can stop the fall.

Now, can I cast Fly on my horse? Can it be considered a willing creature? If so, will I be able to ride it while flying without it needing special training first?

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can I cast Fly on my horse?

It's a creature and so is a valid target.

Can it be considered a willing creature?

Probably; its willing to let you climb on its back, however, your DM has the final call on this. See Can you make an unwilling creature willing? In other words, what defines “willing”?

If so, will I be able to ride it while flying?

Sure, why wouldn't you be able to?

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    \$\begingroup\$ RE: "Sure, why wouldn't you be able to?" In some editions there's a maximum weight a flying creature can carry and still fly (in D&D 3.5 that's a light load if the creature can naturally fly but up to the creature's maximum encumbrance while the subject of the spell fly, for instance). It might be useful to clarify the absence of such restrictions in 5E. \$\endgroup\$ – Hey I Can Chan May 8 '16 at 14:14
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    \$\begingroup\$ Generally the rules for flying weight as suggested by Mearls is to subtract the creatures weight from its total carrying capacity in 5E and thats how much more weight it can take while flying. But since this an optional thing and so very few DMs actually track encumbrance; I think this very direct rules as written from Dale are enough to answer the question presented. Weight mechanics would be a separate question. \$\endgroup\$ – Airatome May 8 '16 at 15:18
  • \$\begingroup\$ In our specific case, the flying creature is a mule and the riding creature is a gnome, so I think that there would be no problems with weight. My only concern was the need to train the creature before you can control it. \$\endgroup\$ – firion May 8 '16 at 16:31
  • \$\begingroup\$ The carrying capacity idea makes sense if the creature is flying on its own strength (using fantasy physics), but less so when it's magic. With that, anything from "no extras" to "some limit based on the caster's" skill to "it's magic, so anything that can fit" seems potentially valid. \$\endgroup\$ – mattdm May 8 '16 at 17:47
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    \$\begingroup\$ @firion If that's a concern you have, it's important to say so in the question, since we can't read minds. :) I've put it in the question for you. \$\endgroup\$ – SevenSidedDie May 9 '16 at 3:24
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I would rule that yes you can, but you would need to train the horse to follow flying commands, and not panic. It takes time to train a horse for even basic riding. But if a player wants to invest the time, sure. Sounds awesome and fun.

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  • \$\begingroup\$ Magic horse training! Start with jump horse, then fly horse. Eventually use polymorph for easy access Pegasus! \$\endgroup\$ – eyecosahedron May 10 '16 at 19:52

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