Welcome Aboard, Monique!
Thank you for visiting the Disney Parks Moms Panel to ask your questions about cruising with Disney Cruise Line!
I have found that often the best cruise prices are in the fall. Sometimes, you just have to try a few different dates that will work for your family and see how the pricing compares. You should be able to find pretty comparable prices in early May and most of September. Also take into account your family's schedule and prices for airfare.
I have cruised in September, but never May. The weather was lovely, Mexico was HOT (late September). I have also been to Castaway Cay in all months except May and November, and we have enjoyed it every single time. We were only unable to swim one time in January (but lots of cruisers were swimming!). It truly is an island paradise, with white sand beaches and crystal clear aqua water.
When planning a Land & Sea vacation to the Walt Disney World Resort, I would highly recommend that you book your land portion to precede your cruise. That way, after you have been running full speed, visiting the amazing Disney Theme Parks, you will relax fully on your Disney Cruise Line vacation. Maybe you will even want to book a massage at the
Senses Spa & Salon onboard!
I hope this helps with the planning for your land & sea vacation. Please visit us again with more questions as your continue to explore your options!
Happy Cruising, Tracy V.