Charles Ellicott Commentary 1 Corinthians 16:6

"but with you it may be that I shall abide, or even winter, that ye may set me forward on my journey whithersoever I go." — 1 Corinthians 16:6 (ASV)

And it may be that I will abide . . .—His former plan had involved only a brief visit to the Church at Corinth, but the arrangement he now contemplated would permit a longer stay. So he adds, with affectionate emphasis, that you may send me on my journey. Where he would go from Corinth he had not yet determined; indeed, it was later determined for him by a conspiracy against him, which was fortunately discovered in time (Acts 20:3).

He remained three months at Corinth during winter, and as that brought him to a time of year when a voyage would be safe, he resolved to sail into Syria. The conspiracy of the Jews caused this plan to be abandoned, and a different course, through Troas, etc., was adopted. (Acts 20:13; Acts 20:17.) The phrase that you may send me on implies not merely that Corinth would be the starting point of his journey to Jerusalem, but that he would set out on that journey with the good wishes and blessing of his Corinthian friends (Acts 21:5).