Hi Erin,
It sounds like you have a great vacation planned at Walt Disney World!
Bay Lake Tower at Disney's Contemporary Resort is a lovely resort. It is so conveniently located. To be able to walk to the Magic Kingdom, and to be able to take a boat to Disney's Fort Wilderness Resort and Campground, are great perks. I also love the
Hoop-Dee-Doo Musical Revue. The entertainment is fun and hilarious, and the food is wonderful. I love the fried chicken there!
Taking a boat from Bay Lake Tower Disney's Contemporary Resort to Disney's Fort Wilderness Resort is a perfect plan for you. You are correct, the boat will drop you off in the Settlement area, which includes Pioneer Hall, the home of the Hoop-Dee-Doo Musical Revue. You do not need to book reservations for the boat. Simply head on over to the back of Disney's Contemporary Resort, from where the boat will depart, and wait for the next boat to come. The children do not need life jackets. I would suggest that you give yourself at least an hour for this trip. While it should not take that long, it is always good to leave yourself extra time to wait for the boat, and to walk to your destination.
Have a wonderful time planning your trip, Erin! Please do not hesitate to ask if you have any further questions.