We live in New England and usually travel during the winter months. We have only once traveled on the day of our cruise and that was out of San Juan..We woke up the morning of our flight and there was close to a foot of heavy wet snow on the ground. We were lucky and still got out on time and made our cruise. Believe it or not, the ship had so many passengers that had booked cruise/air that the ship did not leave until nearly midnight and was scheduled out at 6:00 if I remember. Since then, to keep our sanity, we go to our cruise port 1 - 2 day ahead if we can and it makes for a longer vacation and less stress on our part. We have always looked for reasonable priced/clean accomodations with shuttle and its part of our cruise costs that we plan for. Each to their own and how comforatable one is with travel day of cruise.