Welcome aboard, Earlee! Congratulations on booking your very first cruise with Captain Mickey and his crew! Disney Cruise Line is the most magical way to vacation with family, in my opinion. I've enjoyed sailings on all four of Disney's pixie-dusted ships and simply can't get enough!
The four-night sailings on the Disney Dream do include the popular
Pirate Night with the Pirates IN the Caribbean Deck Party and Buccaneer Blast Fireworks at sea, like only Disney can do! So, be sure to check out those after Halloween clearance sales and grab some pirate costumes and accessories for your whole family so you're all ready for your swashbuckling summer adventure!
As far as dining attire, you will have three cruise casual nights onboard (one of which is Pirate Night), and one Optional Dress-Up night. So, if you want to bring formal wear, that would be the night to wear it. You'll see a bit of everything on the Optional Dress-Up Night, from very formal attire to very informal attire, since it is an optional night. I do always like to take advantage of the opportunity to have my whole family dressed to the nines and get great photos that night! Plus, Mickey and his pals are out in their formal best that night, quite often, so we get some really fun pictures with them!
I recommend you fly in the day before your cruise and stay either at one of the Walt Disney World Resorts or the Hyatt Orlando Airport, as all of these offer
optional cruise ground transfers to the port through Disney. There's no easier way to transition from land to sea and back again than by letting Disney do the driving!
Have fun planning, and please stop back with more questions as you count down the remaining months until your big cruise adventure, Earlee!
Marcy