Hi George!
It's always a pleasure helping a fellow cruiser from IL plan their magical voyage aboard the Disney Cruise Line! As it's pouring freezing rain outside, I would love to share my thoughts on jumping at the chance to book
Port Adventures and other shipboard activities when the clock strikes midnight (EST).
You're correct! First-time Guests are able to book Port Adventures 75 days prior to their cruise during online check-in. Online check-in is based off of Guests' Castaway Club levels and Castaway Club levels are based off of how many cruises you've completed. So, Silver Castaway Club Members get to book excursions 90 days prior to their cruise, Gold Castaway Club Members can book 105 days prior to their cruise and Platinum/Concierge Castaway Club Members can book Port Adventures 120 days prior. The reason I mentioned this is because there will be many of your fellow cruisers already having booked their excursions by the time your advance booking window arrives.
In my opinion, if you have your heart set on a certain Port Adventure, it would be advantageous to set your alarm for 11:59 (10:59 CST) and hop onto the Disney Cruise Line website to try and book it! I've done this multiple times and it's actually really fun! I also suggest researching the excursions ahead of time at each Port of Call during your cruise and make a list of your top three. This way, if your first choice excursion is sold out, you have two more in the queue that you know you've already researched. Finally, if you aren't able to book the one excursion you had your heart set on during your online check-in, I suggest stopping by the Port Adventures Desk, onboard, the day of embarkation! Sometimes people cancel and there will be spots available. If there are no cancelations, you can at least put your family's name on a waiting list.
I had so much fun answering your question!
Beth