Traveling with Family
Traveling with family can be a lot, and I'd be lying if I said I wasn't anxious while building the itinerary for my recent trip to Chicago. With any group, there can be a multitude of competing interests, priorities, and mobility levels, not to mention the complexity of the relationships themselves. However, I was overjoyed with how well the trip went - and it inspired me and gave me the confidence to plan equally complex family trips - Vegas, San Diego, and more up next!
Here are my top tips for planning family travel:
1 - Hold on loosely. Make a plan, but intentionally build flexibility into it.
For a large group, I only plan two things per day: breakfast and one group activity. This strategy avoids a panicked flurry of group texts in the morning trying to plan breakfast, wards off hangry behavior, and is simple enough to ensure the group knows what the "big activity" is for the day. This can be simplified further if everyone is staying in the same hotel and there is an included hotel breakfast.
Not every activity needs to be done together - a mix of full group activities as well as smaller groups gives everyone breathing room and more to talk to each other about during meals. This is a great way to build in time for specific interests. For example, I have been to the Midway Naval Museum in San Diego at least three times and I do not want to go again. I will build in specific time for the people who are interested to go to that museum while I do something that I'm more interested in. Afterwards, we meet for pizza. Everyone wins!
2 - Physical Limitations - do your research, and build in rest
When possible, choose attractions that are weather-proofed - I don't want my grandparents sweating in the sun for hours or getting caught in the rain. If there are attractions that are best when the weather is fair, try to keep that activity flexible and able to change to a day that has better weather if possible.
Example: I chose indoor activities (aquarium and botanical conservatory) for a trip with my grandparents. The weather ended up being beautiful, which allowed them to enjoy the parks near Chicago's lake shore briefly.
Example 2: When bringing guests on a hike in the Smoky Mountains, we always check the forecast. If we can't go Saturday morning, then we'll go Sunday morning and adjust our plans accordingly.
I build rest into a trip by having a lot of blank space in between activities. Then, if it becomes apparent that we have enough time to pursue a “side quest” or additional activity, I have lists of attractions and restaurants we can go to that we can easily pivot towards.
If we are feeling unexpectedly tired from being out in the sun, need to go change due to getting caught in the rain, or forgot the physical tickets for the group activity, this approach provides plenty of time for that without breaking any of the plans.
Example: For a typical group vacation day, I will plan for breakfast (9:30am), group activity (1pm). I take everyone's recommendations for food and activities along with the hours of operation and we have an automatic list that we can pick from for lunch, dinner, and any additional activities
3 - Varied interests: Find common themes that can unite a group
Chicago was especially great for this due to the high number of amazing museums and activities available. One thing I knew that would unite all 3 generations of my family is animals, so we went to the aquarium.
For Las Vegas (upcoming!), my brother and his wife are Gordon Ramsey fans, I know that my parents love special dining experiences, and food experiences are key to travel for my partner and myself - for sure one of our meals will be at one of Gordon's restaurants.
Pizza qualifies as a shared interest inter-generationally, in my experience.
4 - Central storage of information - have all important addresses and plans in a central hub
Use your preference, whether that's Google Docs, OneNote, or a spreadsheet. It doesn't matter as long as it's all in one place AND everyone has access to it.
My preference is to use OneNote and export the document to a pdf, which I then share with the group. Downloading a PDF protects against bad reception/no wifi!
In my planning document that I share with the group, I put the following:
Airbnb/Hotel Addresses
Airbnb Check-in Instructions
Addresses for important locations (graduation ceremony, wedding ceremony, dress rehearsal, rehearsal dinner)
Flight Numbers
Arrival and Departure times
Reservation information/Plans to arrive early
Itinerary of Who is doing What and When
List of potential activities, hours of operation, and addresses
List of potential restaurants, hours of operation, and addresses
5 - Zone Defense - for any family members who need extra care, designate responsible parties
Before entering an attraction, designate who is responsible for what - then rotate so everyone can take turns.
Example - before entering the Shedd Aquarium in Chicago, my uncle was in charge of obtaining the wheelchair. He and I took turns pushing the wheelchair. My husband was designated responsible for making sure my very mobile grandfather did not get lost.
6 - Take the pressure off
If the trip is centered on a specific family member who is graduating, getting married, etc - do everything you can to take pressure off of that person. Offer to help with an unglamorous or boring task, and keep your promises! This is always appreciated.
If you also know that various parts of the family will be vying for time with this person, design a clear time that you'll spend with them if possible, then share your plans and let them know they're welcome to join any of the activities if they are able to, but that there's no pressure for them to attend anything if they are completely covered up in obligations.