All family vacations, especially the multi-generation ones, need a Trip Boss to make it a great trip.
I was lucky enough to travel to Walt Disney World with my daughter, Laurie, the in-laws and the grandkids for a few days last year. Laurie was the Trip Boss for this trip and her excellent planning made it fun and easy for everyone.
There are several attributes a Trip Boss has to exhibit:
1. Deep knowledge of the vacation site
Laurie is a WDW aficionado. She reads many articles and keeps up with the people on social media who basically live and breathe WDW. She researched the different parks, events, and opening/closing hours. Her knowledge of the ins and outs of the different parks came in handy every day. She knew where to be in order to meet characters, which parks have longer lines in the mornings versus the afternoons, etc. Laurie did several advance reconnaissance trips to the parks add to her knowledge.
2. Advance Planning Skills
Laurie started planning this trip a year out. She created a schedule for booking events, because there is a hierarchy to when certain reservations can be made. She got the family on board and figured out dates for everyone to travel. Did I mention that her in-laws live in Ireland? All the international travel had to be coordinated as well. She bought an Annual Pass for WDW, which allowed her certain perks, like booking experiences in advance, and free parking at the different parks, as well as food and shopping discounts. This pass helped with the budget. At prescribed intervals, she booked the Fast Passes, the dinner reservations, the transportation.
3. Soliciting and Receiving Input
Again, well in advance, Laurie asked for input from the group. Her husband wanted a day to go to the Everglades, so she built that into the schedule. Some of the group wanted to go to the Outlet Malls, so she made space in the schedule for them to do that. If there is enough lead time, it is easy for everyone to communicate their desires and get those into the travel plan.
4. Smart Scheduling Skills
This is where organization skills come into play. Laurie planned all the major activities, beginning with which park should be visited each day. Then she created a daily touring plan to detail the path through the park. She coordinated which rides would have fast passes (an important skip-the-line feature of WDW park rides), where the group would eat lunch and places to have snacks and chill out. Laurie allowed for flexibility for members of the group, like taking the ages and interests of everyone into consideration for what they would do each day. She had a mix of early mornings and later evenings. Before the vacation started, Laurie created a timetable spreadsheet for each day and sent that out well in advance so everyone would be on the same page (literally) for activities.
5. Group Cooperation
The Trip Boss needs to engender group cooperation for the plans to work smoothly. This family was quite happy to have every day planned for them and know what to expect. If the morning departure time was 8:30, everyone made an effort to get up and be ready by 8:30. If they were to meet somewhere to leave at 4:30, this group kept to the time table or let someone know if they were doing something different. They created a family WhatsApp group to stay in touch throughout the day.
Having a cooperative group is one of the most important factors in a successful family vacation. This one worked because everyone made the effort to be part of the group.
