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10 Essential Tips for Planning a Group Trip (2023)

This year was a huge year of group travel for me. I personally took several group trips with friends or extended family. I also helped plan a couple of trips for large groups.

I learned a lot during this - and usually not the easy way - so I wanted to share my lessons and tips with you.


Going on a group trip can be a great way to bond with your friends and make lasting memories, but it doesn’t always come without its challenges. With careful planning and preparation, you can enjoy a hassle-free group getaway. Here are seven essential tips to help you plan the perfect group trip.


Decide on a Destination.

Establishing a destination for your group trip is one of the most critical steps towards planning. You’ll need to consider factors like budget, travel time, and interests when selecting a destination.


Brainstorm together and take polls to determine where the group would like to go—whether it’s an international adventure or something closer. Answering this question first will make the rest of the planning process smoother and help ensure everyone is happy with the outcome.


This fall, my friends and I went to Bar Harbor and Acadia National Park. We had initially dreamed of a beach vacation but happily settled on leaf peeping in Maine once we looked at calendars and realized that the only week we could get together would be prime time for New England.




Figure Out Everyone's Budget and Understand Differences.

Even if you have similar incomes, you may have different levels of debt or different preferences to how to spend your money.


If you genuinely want to go with certain people, you should be willing to meet everyone’s budget. That may mean that a cross-country flight is off the table in lieu of a trip that is within driving distance.


It may also mean that instead of fancy dinners, you prepare your own meals or eat at places that are moderately priced. I have one friend that has an excellent salary and much disposable income. She enjoys eating at nice restaurants and often orders more than one dish because she wants to try things.


Sometimes, this drives me nuts. Likewise, she doesn’t want to hear from me or anyone else what she can and cannot order. Fortunately, she’s also very generous and is always willing to share (which of course she doesn’t have to do) and often covers or over-covers her expenses.


Bottom line: understand budgets and preferences early and you will mitigate most problems during your trip.


Manage Group Expenses During the Trip

A couple of years ago, a different friend introduced me to the app “Splitwise.” It is a game changer to help with managing group expenses.


You can create a group (e.g., the trip name) and then invite your friends to the group. Each person can add any expenses that are incurred and easily delineate if the cost should be shared and if so, how so. You do not have to share equally and can select a percentage or dollar amount.


You can also remove group members from that particular line item. In the end, you can settle up through your payment method of choice.


Create a Timeline and Itinerary Informed By Everyone’s Preferences.

Aside from money management, this is the biggest difference in how well a group trip goes.


Consider all the possible activities before you go on a trip and have everyone give one or two things that they really, really want to do. Knowing what other things people are interested in but can live without is also helpful. Are there any things that people do NOT want to do? That’s helpful too.


Make an agenda that considers all these things but may not be perfect. Ensure you have enough time for each activity, preparation steps, transportation, meals, rest periods, and more.


Provide each group member a copy of the plan so they’re always on the same page throughout your trip.


Encourage People to Opt In or Out As They See Fit

Here’s the challenging but essential part: let people opt in or out as they see fit. If you are active and/or like getting up early and doing things, don’t make the less active person do a million things. Or make the later sleeper get up early on their vacation.


My dad always wants to scrap group plans if everyone doesn’t want to do it. He thinks we should all be together. I disagree. We usually come together late afternoon or early evening, so we still have quality time together. I agree that is important to find a time that everyone can agree to get together, but resentment builds if people don’t get to do what they want to do.


Communication Is Key

Communication is essential when planning a group trip. Make sure everyone in the group knows all pertinent information and regularly shares updates. Utilize apps such as WhatsApp or GroupMe to keep everyone in the loop with travel updates, deadlines, and reminders.


Also, it’s important to remember that each person has different communication styles and needs. Ensure everyone is heard by creating a space to provide feedback or express concerns throughout your trip planning process.


Allow Deviations from the Plan

Before you leave, you can come up with a great plan. But when you get there, you may change the pace or the activities based on new knowledge or how you feel in the moment. That’s OK.


Acknowledge Different Fears / Comfort Levels

This one was really driven home to me on a trip to Acadia with my closest friends. I had arranged the agenda and selected a few hikes for us to do while there. One of those was the Bee Hive trail. It’s 0.9 miles straight up a mini-mountain and includes narrow ledges, extreme heights, climbing small ladders, and in some cases, walking over grates. It's appropriately named the "Bee Hive."


I found it exhilarating. Another friend appreciated it at the end but was nervous throughout. My other two friends wanted to kill me. We’ve been friends for years but had never hiked anything that high or nerve-wracking.


My lesson learned was to really understand a hike before doing it and make sure to communicate any challenges to my group before deciding on behalf of everyone. I could see this lesson applying to any other adventure activity: know what you are getting yourself and others into before committing to it!



3 women climb Bee Hive Trail and look up at the photographer while you see the ocean and the rest of Bar Harbor in the background.
Bee Hive Trail, Acadia NP. Those aren't genuine smiles:)


Try to Understand Daily Routines

This was another funny lesson from Maine. And also Thanksgiving with my family. Actually, all of the group trips.


We stayed at a beautiful cabin that belonged to a friend of a friend in Maine. It had two rooms and there were four of us so we split into groups of two. My friend, Julie, and I had already learned on our cross-country trip over the summer that we both snore. On this trip, our other friend, Stephanie, was clued in and unhappy about it. She wanted to sleep on the couch but that didn’t work out for the rest of us because we all like to stay up late and she likes to go to bed early and get up early.


If we had such an opportunity again, we’d make it work as we did this time. But if we are starting anew, I think we are all realizing that we may each need our own room.


Additional Questions or Considerations for a Group Trip

You’ve now learned how to plan a great group trip. Here are some questions that are worth addressing while planning your trip.


Personal Preferences

  • How does your travel style differ from the group?

  • Who needs to be part of the plan vs who can just roll with it?

  • How do you manage people that plan vs people that want to take time and see where the day takes them?


Habits

  • Does anyone snore?

  • Who takes a lot of time getting ready vs who can be ready fast?

  • Are group members militant about time or habitual procrastinators?


Money Considerations

  • Are some folks more cost-conscious vs splurgers?

  • What is everyone’s budget for accommodations? Air travel? Car / Ground Transport? Food? Activities?


Getting Around

  • Who does/does not like to drive?

  • Does anyone have poor eyesight at night or in poor conditions?

  • Does anyone have motion sickness?

  • How do you decide who’s Designated Driver (DD) or take a car service?


Health and wellness

  • Does anyone have a fear of heights? Fear of air travel? Other fears?

  • Are there food allergies?

  • Does anyone have physical or other limitations?


I hope this helps you with future group trips. SAVE for later and share with a friend who may benefit from this!


Happy Travels,

Chrissy

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