Hi Bree, welcome aboard!
My kids absolutely love
Pirate Night on Disney Cruise Line! There will be no shortage of pirate gear available for your boys on the Dream. The last time we sailed on the Dream, my son was thrilled that the Oceaneer's Club had a pirate face-painting activity. He came out with a painted beard and a very pirate-y looking scar! These types of activities are always subject to change, so check your Personal Navigator the morning of Pirate Night to see what offerings are in store for the kids that day.
If you have pirate costumes for your sons, bring them! And throw in some pirate gear for the rest of your family too! Pirate Night is not just for the kids! One of my favorite memories is seeing my children's grandparents all done up like pirates on the Dream - parrot on the shoulder and all!
Each time we've sailed, we've found Disney's Pirates IN the Caribbean bandanas waiting on our beds before dinner on Pirate Night, so you can expect to receive those for your whole family. If you don't bring pirate gear from home, or you find that you need an extra accessory, the shops onboard will have pirate merchandise galore, so no need to worry! You'll see families wearing anything from just the pirate bandana with their regular clothes, to families in full-out pirate regalia! No matter where your family falls on the pirate dress scale, you're going to really enjoy that night!
Have fun planning the rest of your cruise, Bree, and please let me know if you have any other questions! I'm happy to help you make the most of your Disney cruise!