How to Plan Travel with a Group

Updated June 16, 2020.

It’s Motivation Monday! Someone recently asked for advice on planning travel for her family–three adult children between the ages of 19-25, one with special needs; a mother who loves to shop; a father 35 years older than the mother who loves history but has a hard time getting around, so hiking is not a good idea. That’s a tough trip to plan! So I was inspired to write a blog post with some tips and strategies to make travel with family or friends manageable–and with everyone still on speaking terms by the end of the trip!

Decide Where to Go

First of all, everyone needs to agree on a place! Maybe it’s someone’s birthday, so they get to choose. Or maybe it’s an anniversary, so the happy couple gets their pick. Or maybe your friend just got their passport, and they want to test it out in a country they’ve dreamt of all their life. Or maybe your friend already decided on a place to go, and then they asked if you’d like to join!

However you decide where your group should visit, do not vocalize regrets or wishes for somewhere else once the decision is made. You can choose next time! I told my sweet husband to choose our honeymoon location because I had too much on my plate with wedding planning. I knew Scandinavia was somewhere he’d wanted to go, but I was not thrilled at the aspect of a cold honeymoon destination. When all was said and done, Scandinavia was the one he chose–and we both loved it! I packed a variety of layers and was just thankful he did all the planning; and it’s still one of my favorite trips to date!

Get started right! How to Plan a Trip

List Everyone’s Interests

When you all figure out where you’ll be going, take some time to list out what each person is interested in seeing and doing. Not everyone will want to do all the same things, and that’s ok! Everyone should have a say in the trip planning, whether they like shopping, history, museums, hiking, beaching, etc. There is a way to make sure everyone enjoys the trip, and that is to make sure everyone’s preferences are heard and addressed.

Your list should include:

• Each person’s interests (history, art, architecture, tours, food, shopping, ships, reading, people watching, hiking, taking it easy, fitness, etc., etc., etc.).
• Each person’s “want to do” activities; these can be any and everything and will probably get pared down quite a bit in the planning process–some things will be too far away or too expensive to be practical, some will not fit into the timeframe, and some will work out perfectly!
• Each person’s 1-2 “must-do” activities; these should be considered non-negotiable by everyone in the group, so don’t go over 1-2 per person (going to the top of the Eiffel Tower, hot-air ballooning in Cappadocia, hiking the Kalalau Trail, shopping at Harrod’s, visiting the Silos in Waco, eating P.E.I. mussels on Prince Edward Island, snorkeling at the Great Barrier Reef–dream big!).

Be Prepared: What to Do If Your Travel Buddy Drops Out

Don’t Be Afraid to Divide and Conquer

No two people have the exact same interests, attention span, patience level, or physical ability. But here’s the solution: it’s ok to go your separate ways! When you have a day set aside for everyone to do their own thing–or for two of you to do something you both want to do while your third friend does something that doesn’t interest either of you–you can come together refreshed that evening to swap stories over dinner.

For instance, I went to Nova Scotia with my mom and younger brother a few years ago. We had a great time, but one afternoon my mom wanted to take a nap when we had scheduled time for my brother to visit the cemetery where many passengers from the Titanic are buried. We didn’t all have to go, and we didn’t all have to take a nap! We let my mom rest and my brother and I paid our respects. No one got their feelings hurt, no one had a meltdown, everybody got to do what they wanted to do!

MUST READ: What to Know About Your Travel Buddy

Personally, I think this is the #1 way to save relationships and return from your trip on speaking terms. You chose to travel together because you like each other, right? But everyone needs space and time to themselves, or just to mix things up a little bit every once in a while. Don’t put pressure on everyone by thinking you have to do everything together 24/7. There has to be give and take, and sometimes you need to give and be given some space.

Splitting the Bills

This is perhaps the most awkward part of traveling with friends or family, especially when parents and adult children travel together. Who pays up front and who writes a check to the person who paid up front? How do we figure it out? When do we exchange payment? It’s a hard one, but it’s not impossible! There are apps to keep track for you like Splitwise and Settle Up, but if you’re less tech savvy or traveling with people who are, here’s a quick run-down of how to navigate payments.

More travel apps here: The Best Apps for Travelers

Big Ticket Items that Have to be Paid Before Travel Time

These are things like plane tickets, accommodations, rental cars, event tickets, and other items that need to be planned in advance. The easiest thing to do is:

• Assign one person to pay for all of these (and getting those credit card points is a good enough incentive for me), but do not purchase yet
• Add up the cost together (whether in person, on the phone, or via Skype or FaceTime) so there is complete transparency, then divide accordingly
• Assign a deadline for payment to the person who pays (or better yet, everyone bring their checkbooks, online payment know-how, or cash so you can pay immediately)
• When payment has been agreed upon, purchase those big ticket items

Payments On Travel

Where possible, everyone should pay for their own meals and such when traveling. In cases where this is not possible (for instance, if the restaurant where you’re eating does not give separate checks), pool each person’s share in cash, or let one person pay with their credit card pay them back as soon as possible.

This is very important. I made the mistake once of paying for everything up front (except plane tickets, whew), and the plan was for the two people I was traveling with to pay for my meals, excursions, souvenirs, etc., until their shares were paid back. Unfortunately, the piece of paper we were using to keep track of that was lost. Bummer.

Get rewarded for the money you spend on travel!
Beginner’s Guide to Credit Card Points

I hope this post was very helpful and encouraging for you! Traveling with a group has its benefits, but it can be intimidating, too. Unless you know the right strategies! Want a few more helpful resources? Check out these blog posts for more:

• How to Read a Map
• How To Road Trip
• How to Trip Plan with Trip Advisor
• Your Ultimate Guide to Accommodations
• 5 Habits of Flexible Travelers

And don’t forget to check out all my best travel hacks on my Travel Tips Page, and my planning resources on my Travel Planning Page!

Love this post? Pin it for later!