Hi Lisa! Thanks for stopping by the Disney Parks Moms Panel!
This is the ultimate in planning! I love your question!!!
There are several opinions regarding footwear in the Theme Parks, but my family is 100% in favor of tennis/walking/running shoes. They provide support and protect your feet. We typically walk 7-15 miles per day with a 9 and 11 year old when we are at
Walt Disney World Resort. I'm confident 14 year old twin boys will have more stamina than my kiddos so be prepared for lots of walking.
Sunscreen, sunglasses and hats are important to protect them from the warm Florida sun. You may also experience some rain as it typically rains 10-12 days in May. Moisture wicking clothes are great for both the sunny and rainy days and you might also want to bring or buy a rain poncho depending on the amount of rain you receive while you are at Walt Disney World Resort.
Water...water is important for all! Take water bottles (no glass containers) with you and stay hydrated! A small backpack or cinch sack for each of your boys might be helpful so they can carry their water, sunglasses, etc.
I would also suggest taking swimsuits with you. An afternoon break at your Resort hotel swimming pool is always a great way to get re-energized for a fun evening in the Theme Parks.
As you are putting the final touches on your vacation, you might want to take a look at the
attractions well suited for teens. You might find something you want to include in your itinerary.
I hope this helps you with your planning. Please let me know if you have any other questions as you plan your magical Walt Disney World Resort vacation. I'm excited for you to see the magic through their eyes. Enjoy every moment!
Kari