How to Plan a Multigenerational Trip

If you’ve ever planned a family trip that spans three (or more!) generations, you know it’s not just about finding the destination. It’s about creating a meaningful experience that works for young children who need naps, teenagers who need plenty of activity, and older adults who may have mobility concerns.

With one in three families now embracing multi-generational travel, trips such as these have become less about obligation and duty and more about seizing precious opportunities to record core memories across generations.

The key to successful, safe multi-generational trips is considering everyone’s needs without sacrificing enjoyment. Whether your family is dreaming of a beach resort in Hawaii, a cultural tour across Europe, or a cozy mountain skiing getaway, this guide will help you evaluate the unique dynamics of your multi-generational group and ensure that everyone not only has a good time but also arrives home safely.

Let’s get started!

Step 1: Start with a family meeting

The foundation of a successful multi-generational trip starts with a good old-fashioned family meeting. It helps if you frame it as the trip kickoff celebration rather than a formal discussion.

Gather everyone around in person or on a video call, and make it fun with snacks and maybe even destination-themed treats (assuming you’ve chosen a destination). 

Start the pre-trip planning session with these key discussion points:

1. Everyone’s health and safety comes first! This means:
   • Individual sharing of comfort levels with various activities. 
   • A discussion around medical check-ups in the planning stages (necessary for travel insurance decisions).
   • Discuss the need to create plans to manage medication and any medical needs during the trip.
   • Talking openly about mobility considerations, walking distances, and planning for rest periods.
2. Next is creating a digital documentation game plan. This means assigning a person to create a shared digital folder that will hold:
   • Medical documents (like doctor’s notes)
   • Insurance and travel insurance cards
   • Emergency contacts for each traveler, including primary doctors
   • Current medication lists and schedules
3. Finally, there is the task of preparing for medical emergencies. This means assigning one or two people to:
   • Research travel insurance options for individuals or for the group
   • Research medical facilities at the proposed travel destination

Pro tip: You can make the meeting interactive (and quieter) if you have family members write down their top concerns on a shared whiteboard or sticky notes.

Step 2: Clarify accommodation needs

Think of your family’s accommodation as the command center for the trip. With this in mind, you can see how the lodging must serve as a comfy haven and also a practical base for daily adventures.

With your family meeting notes in hand, look for properties that offer a mix of communal spaces and private retreats, such as hotels that offer adjoining rooms or vacation rentals with multiple bedrooms and a couple of common living areas indoors and out.

Features to consider include:

1. Ground floor rooms or reliable elevators
2. Bathroom safety features like grab bars and walk-in showers
3. Bathtubs for small children
4. Short walking distances to activities and restaurants or easy-to-use public transportation
5. Kitchen facilities for flexible meals and accessible snacking
6. Quiet areas for afternoon snoozing
7. Proximity to medical facilities

Pro tip: If you have specific questions about a property, calling the manager is the best way to ensure your family’s specific needs can be met.

Step 3: Smart transportation strategies

If you’re careful, getting there should be half the fun and not double the stress. Smart transportation planning for multi-generational groups requires thinking through every stage of the journey. 

Key transportation strategies include:

1. Airport logistics, like:
   • Booking wheelchairs in advance
   • Allowing extra time between connections
   • Booking direct flights whenever possible
2. Ground transportation logistics, like:
   • Reserving vehicles with easy entry/exit options
   • Booking rentals with ample storage space for everyone’s stuff
   • Arranging private transfers for group convenience when possible
3. Daily transportation logistics, like:
   • Keeping drive times short (or at least manageable with breaks)
   • Having rideshare apps downloaded and ready
   • Accessing public transportation when useful

Pro tip: Share the transportation strategies with the group so everyone knows what to expect and what steps they need to take to prepare.

Step 4: Activity planning and pacing

Successful multi-generational trips aren’t just about where you go and what you do, they’re about how you structure each day. Think of your trip itinerary as a playlist that mixes high-energy songs with slower-paced ones.

The goal is to build a flexible itinerary that allows each person some freedom while addressing the need for together time.

Consider an itinerary broken into three basic timeframes:

1. A morning routine that includes:
   • Breakfast together to allow time for medication routines, vitamins, caffeine, etc.
   • Daily activity review (so everyone knows where others are going)
   • Built-in flexibility for those who resist mornings and morning people
2. Afternoon balance that includes:
   • Designated quiet times after lunch (benefits both other adults and young children)
   • Optional high-energy activities for those who need a boost
   • Built-in flexibility for peak heat hours, if needed
3. Evening settle-down that includes:
   • Group dinners at places that accommodate various dietary needs
   • Calm evening activities like photo shares, after-dinner walks, and stories
   • Built-in flexibility for bedtimes without guilt

Creating a flexible daily menu of opportunities rather than a rigid schedule will allow individuals to opt in or out of activities while ensuring that everyone has something to look forward to and no one gets lost or left out.

Step 5: Strong communication strategies

Before departing, create a strong communications plan that keeps everyone safe and connected without causing anxiety.

The following are the elements of a clear communication strategy:

1. Set up a group chat and make sure everyone knows how to use it
2. Designate a primary point person for emergencies (they will have the medical and insurance documents to hand)
3. Establish meeting points at each destination so everyone knows where to go in an emergency
4. If the trip is international, make certain everyone’s phone will work while abroad
5. Design a buddy system for when the group splits up and an end-of-activity or end-of-day gathering point

Pro tip: Don’t rely solely on phones and Wi-Fi access. Print out the essential details like medical information and travel insurance documents, and have a point person carry them.

Step 6: Build in memory-making opportunities

Now that you’ve gone through the headache and effort of creating the perfect multi-generational trip, don’t forget the most important part: creating memories.

The most cherished memories often happen at the moment, but some can also be carefully planned.

Some options include:

• Arranging ahead of time for professional family photos at iconic locations
• Plan inter-generational activities like cooking classes or cultural tours that highlight family heritage
• Creating a shared digital photo album with travel journal entries from each person

Remember, the true value of a multi-generational trip isn’t checking off the bucket list—it’s in the shared experiences and stories that will be told and retold at family gatherings for years to come.

Planning a multi-generational trip can seem like completing a complex project, but the reward of seeing two or three or more generations connect, laugh, and see each other makes all the work worthwhile.

Related topics

• 10 Tips for a Safe Family Beach Vacation
• How Travel Insurance Covers Kids
• Tips for Safe Travel with Young Children