For the purpose of discussion the only alteration of what we now know to be true about the Earth will be the removal of North Amerca and South America and the Carribean Islands- including those pesky Bahamas that got in his way the first time. Everything else stays the same- most importantly the size of the Earth.
If he had very nice weather, was Columbus adequately prepared to make it all the way to India going West across an Ocean that spanned the globe? Did he have sufficent supplies?
Suppose we allowed him to stop before reaching India. Could he have reached the Philipines or magical Cipangu? Suppose he was lucky enough to happen across Hawai’i, could he have even made it that far?