We have gone in , April, June, September, November, December and January in the past few years. Here is the breakdown of times we have missed
Castaway Cay on each cruise and why.
April: None
June: None (Bahamas)
September 2 cruises, None :Mexico, Caymans, Jamaica
November: None (Mexico, Caymans)
December: None Bahamas
January: 1 " Mechanical challenges" Tortola and St. Thomas.
We are booked to go again late September to Tortola, St. Thomas.
Yes, hurricane season is from June 1st to November 30th, but honestly, August, September and early October are the most likely months to have hurricanes.
Thankfully, we have never had a problem, but on our last cruise in September 2015, the cruise that left after us, experienced the tail end of Joaquin and sailed safely around it. Although, there was a delay in getting into port if I recall.
In January, you might get a day or two of cool weather in Orlando and Bahamas, but definitely awesome weather in the islands.
A 2:30 flight should be fine if you get off the ship by 9 and get to the airport by 11:00 (very easy as it is about a 45 minute drive to the airport)