Hi Cassandra,
Any time you visit Walt Disney World for several days or plan more than one visit in a year, I think it's worth doing the math to see if an annual pass would be advantageous. As a passholder, you are eligible for lots of discounts, including on resorts, merchandise and dining. For example, many restaurants offer a 10 percent discount to passholders, and, through September 30, 2017, 45 restaurants are offering a 20 percent discount on dining in honor of Walt Disney World's 45th anniversary.
If you are planning to stay outside Walt Disney World property, the free standard parking that is offered to passholders can be a great benefit. You'll find a
complete list of discounts and benefits here.
I know several people who buy one pass to get discounts for the family. The only downside I can think of would be that passholders can hop among parks and others might not have parkhopper tickets. We've been passholders for almost 20 years and while our daughters were in college, we didn't renew their passes. However, we still visited Walt Disney World together. We just made sure they had parkhopper tickets on those visits so that we can all move among the parks together easily.
You can buy an annual pass for anyone in your family at any time. The only issue you might have is if you activate them at different times, then they would expire at different times. However, your passes won't be activated until the day of first use, so you can stagger the purchases and activate them all at once if you want.
I hope that's helpful, Cassandra. Once you study the discounts and benefits, you'll be able to estimate how much the passholder discounts might save you if you purchase a single annual pass and whether it would be a savings for you.
Please let us know if you have more questions. We're happy to help!
Wilma