The Cherries winger has impressed during his time at on the south coast but has just one year remaining on his contract.
Speaking on Sky Sports' show The Debate, Sherwood urged: “It's important for him to go somewhere and not have two years off.
“The next move for him, and no disrespect to Bournemouth, is one just underneath [the top six].
“Like a Leicester or an Everton. And then he's still young enough to make that next step."