Hello, Anne!
Thank you for sharing your fantastic idea with our planDisney team. I'm so glad you're retiring and going out with a bang to reward this lady who's been with you along the way. I'm sure she is going to love it!
Since you're in Massachusetts, I think it could be a good idea to gift her a trip to the
Walt Disney World Resort in Florida. The flights from Massachusetts would be cheaper, and you'd have more budget for accommodations, tickets, and extra pixie dust.
Depending on how big her family is, you could fit a 6-day trip with tickets in that budget and add some gift cards to cover meal expenses, for example. The
Disney Resorts Collection has a wide range of possibilities between luxurious hotels such as Disney's Grand Floridian Resort & Spa and budget-friendly options such as
Disney's Pop Century Resort.
Since you have a fixed budget, you can choose a mid-range hotel such as
Disney's Art of Animation Resort or Disney's Port Orleans Resort - Riverside and offer them a more extended trip. I'd suggest an 8-night trip with a total of 5 theme park days, one water park day at
Disney's Typhoon Lagoon, and one downtime day at their resort. This option could be interesting if she and her grandchildren have never been on a Disney vacation.
If you'd rather send them to California, you can also consider a trip to the
Disneyland Resort. In this case, I'd recommend a 5-night trip with three park days.
In both scenarios, I think the best option to make it happen is to reach out to a travel agent you trust, give them the budget and have them plan a sample trip. Then you can gift it to your secretary and let her work with the travel agent to lock in the dates and finalize the details. How does that sound?
I know she will love this gift, Anne, and we'd be delighted to help you and her refine her plans. Please let us know if you have more questions and we'll help you both!
May the magic be with you,
Julie