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Expert Tips for Organizing a Successful Multigenerational Trip

I’ll confess that I felt some apprehension when our party of 12, spanning ages from two to eighty, arrived in Turks and Caicos last Thanksgiving. While I was looking forward to reconnecting with my sister-in-law from San Diego and savoring drinks on the beach in November, the prospect of sharing accommodations for a week with my husband, our two preschoolers, my two college-aged stepchildren, my sister-in-law, her two children, her boyfriend, and my in-laws was daunting. Fortunately, thorough planning and open communication allowed us to create an itinerary that kept everyone content, for the most part.

Lessons Learned from Planning a Multigenerational Trip, with Insights from an Expert

Mickie Simon, a licensed clinical social worker in Washington, D.C., emphasizes the following key points:

Early Planning Is Essential

Organizing a vacation involving grandparents, siblings, and children demands meticulous advance planning. It’s advisable to start planning well in advance, possibly a year or more ahead, to coordinate everyone’s work, school, and custody schedules effectively.

For instance, in my extended family, we had to navigate two sets of custody schedules—my husband’s and my sister-in-law’s—before finalizing our trip to the Caribbean for my father-in-law’s 80th birthday celebration last year. We ensured that all the kids could join us for Thanksgiving week and synchronized our work commitments and school calendars to make the trip feasible.

Additionally, it’s crucial to determine the ideal duration of the joint vacation for your family. While some may thrive on extended stays, others may find tensions escalating after a few days.

Establish Financial Agreements in Advance

Discussing expenses upfront is crucial when traveling as a group to ensure everyone is comfortable with the financial aspect of the trip. Each household likely has unique financial circumstances, and individuals may have varying comfort levels regarding vacation expenditures.

Initiate conversations about costs by addressing questions such as:

  • What is our overall budget for the trip?
  • Will each household cover their own travel expenses?
  • How will accommodation costs be divided, especially for shared spaces like rental homes?
  • How will meal expenses be managed?
  • Will entertainment costs be covered individually?
  • Are there any participants gifting part of the trip to others, and is everyone in agreement with this arrangement?

Agreeing on these financial details beforehand can prevent discomfort and disagreements later on, ensuring that the focus remains on enjoying the vacation rather than fretting over financial matters.

Choose a Destination that Suits Everyone

Avoid assuming that activities enjoyed in the past will appeal to all family members now. Preferences change as individuals age, new family members join, and parents grow older.

Consider what activities the family enjoys doing together, their activity levels, and their willingness to compromise and involve everyone in the planning process, advises Simon.

For our trip to Turks and Caicos, we enlisted the help of a travel agent we had worked with previously to alleviate the research burden. By providing our agent with details such as our budget, travel dates, preferred accommodation type, room requirements, departure cities, and preferred activities, we identified a destination that catered to every family member in terms of accessibility, activities, and budget.

Embrace Flexibility and Respect Individual Choices

Flexibility is key when traveling with an extended family group due to varying interests and activity levels. Different age groups within the family may have distinct preferences and paces, requiring a balance between group activities and individual downtime.

Establish clear expectations regarding group participation and allow individuals the freedom to opt-out of certain activities, suggests Simon. By including everyone in dining and activity plans while also permitting personal time, families can accommodate diverse preferences and needs.

In our family, we adopted an inclusive approach while acknowledging that households may choose to skip certain activities. We scheduled joint dining and activities but incorporated opportunities for family members to pursue independent interests, like having breakfast separately or enjoying the pool alone.

Incorporate a Special Group Activity

A standout moment from our trip was a professional photo shoot gifted to my father-in-law for his milestone birthday. Despite initial concerns about attire and early morning timing, the experience brought us together and created lasting memories.

Whether it’s a photo session, an excursion, or a celebratory meal, planning a special group activity can strengthen bonds and foster goodwill among family members. According to Simon, shared moments of joy contribute to positive relationships, reducing emotional reactivity during challenging times.

Prioritize Personal Time

Traveling with family, even under favorable circumstances, can be stressful, particularly for the designated planner fielding constant queries. To alleviate stress and maintain well-being during the trip, it’s essential to carve out moments for personal relaxation.

Allocate time for solo activities like a beach stroll or quiet coffee break to recharge and unwind. By including personal time in the itinerary and communicating this need to family members in advance, everyone can benefit from individual downtime, enhancing the overall vacation experience.