Flying into a debarkation port and spending one night prior to boarding is very risky with all the delays, cancellations and lost luggage issues that travelers are encountering. Flying in the day the ship leaves is way to risky and stressful.
We have been cruising regularly with Regent for 22 years. We have never flown in without spending at least two nights prior to embarking the ship. The only exception is boarding a cruise that leaves from Miami.
If you use Regent Air you may have multiple stops .