What trip was Paul planning at this time?

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His third trip to Corinth.

Paul had established the church in Corinth in A.D. 52-53. Then he worked for three years in Ephesus, from A.D. 54-57. While he was still in Ephesus, in the spring of A.D. 57, Paul wrote First Corinthians.

It is believed that just after he wrote the first epistle, and before he journeyed to Macedonia, he had visited Corinth (200 miles distant) because of the problems that had arisen there. Then he had returned to Ephesus.

This was the second time Paul was in Corinth first in A.D. 52-53, and then in the spring of A.D. 57.

Paul had left Ephesus in the summer of A.D. 57 intending to spend the winter in Corinth, which he did. He passed through Macedonia on the way, visiting Philippi and Thessalonica.

Paul wrote Second Corinthians while in Macedonia. Thus he refers to his proceeding south to Corinth for the winter of A.D.57 as "the third time I am ready to come to you."