Ahoy, Mike!
Parasailing is my favorite Port Adventure to experience on Disney Cruise Line's gorgeous private island,
Castaway Cay. Not only do you get a bird's-eye view of paradise, but it's surprisingly peaceful when you're in the air! I've parasailed on three different visits, and I've loved it every time. Unfortunately, on our last voyage, our parasailing adventure was cancelled due to high winds, so I guess that's a good reason to book our next cruise and give it another try!
While your boys must be accompanied by an adult to participate in the Castaway Cay
Parasailing Port Adventure, I'm not sure if that only means on the boat, or in the air. We've always taken turns flying with our two kids, so I've never asked if they could go up together (though they would love that!). As the captains of the parasailing boats are independent contractors, it would be hard for me to give you a definite yes or no answer when it comes to your two boys being allowed to tandem parasail together. A lot depends on the weight limits and restrictions of the flyers, as well as the distributed weight of the passengers in the boat. As flyers go up, the captain and his mate will often ask the passengers to rearrange into certain seats to distribute the weight evenly.
My advice would be to check in with the Cast Members at the Port Adventures Desk on Deck 5 once you're onboard the Disney Dream, and ask if the boys would be able to fly tandem. They're super helpful and would have a better idea about how the boat captains pair up flyers. I hope it works out, and your boys will be able to experience this super-fun adventure together. What memories they'll be making!
I hope you have an amazing vacation next week, and that your visit to Castaway Cay is nothing short of magical! - Diane W.