Traveling with Friends (7 Tips & Mistakes to Avoid)

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Have you ever decided to take a trip traveling with friends to find out later that it was not such a good idea? Looking at our friends’ photos and videos of their journeys can inspire and make us wish that we were there with them.

Over the years, I have traveled solo, and I have traveled with different groups of friends.  I have learned the hard way about who I can travel with and who I can’t.

Going places with friends have created opportunities to bond and reminisce while also developing memories for a lifetime. We learn from each other, share inside jokes and have plenty of laughs along the way.

Different Sides of Friends

We all love our friends and family, but you get to know different sides you might have never seen before you are with them for a vacation.

Let me give my disclaimer; I am not speaking about any one of my friends or family members in particular. Any resemblance is simply coincidental and meant as a generalization.

Let me share some lessons learned over the years about traveling with friends. Hopefully, my experiences will help you make good decisions about your next travel partner and contribute to an enjoyable travel experience.

There is nothing worse than spending your money and time on what could end up being a memory you would like to forget. Remember, group travel is all about compromise.

Tips When Traveling With Friends

Determine What You Want From Your Trip

First, decide on what you want from your trip.

We all have different expectations for our travel.  Remember that Now is Your Time, a previous article.

One person might be a late riser and prefer being spontaneous, while others want to get an early start to fit in as much as possible.

Members of the group must agree before traveling together.  Remember that communication and compromise will be part of the social contract to get what you want from your trip.

Determine if the trip’s primary focus is to have a personal development retreat, go to a music festival, cultural experience, spa/relaxation, or volunteerism?

There could be any number of motivations for your trip. Deciding on expectations needs to be made upfront.

If you don’t reach an agreement initially, things are likely to go off the rails once you are on the trip.

Plan the ‘Must Do’s’

Discuss what everyone wants from the trip, including anything that each person feels is a “must-do” for them.

There will likely be some overlap and, therefore, more agreement.  But if someone’s must-do activity is a niche interest, decide whether to stick together or split up.

If you leave time in the schedule, each person can set out to pursue their interests without feeling like they deserted the group.

For me, having alone time is vital to my disposition with the group.

Consider Your Travel Personality

When traveling with others, what is your travel personality? Even though you might be friends, not everyone is compatible when spending long periods together.

It is meaningful to consider whether you are an early riser or want to sleep late on vacation.

Are you a planner, or would you rather be more spontaneous when it comes to activities? Maybe you’re the person that wants to do the same thing no matter where you go.

Be sure to consider your travel personality and your travel buddies’ also.

Set a Trip Budget

When traveling with friends, it is crucial to set a trip budget ahead of time.  We all manage our finances differently.

Some of us may be more committed to our budget than others. Set some financial ground rules to reduce uncomfortable conversations.

You might decide on a daily budget for activities and be flexible to operate independently of the group if they want to exceed the budget.  

Setting a trip budget will also keep you from feeling that you are preventing your friends from doing what they want to do.

There is no need to budget to the penny but a general idea of how much should go toward big things like transportation, accommodations, and entertainment.

Pick Your Dates & Divide the Work

As a group, pick your dates together.  After that, you can decide how to move forward on all of the other logistics.

The person who is most skilled at planning will often volunteer for the bulk of the planning.

Even if you’re a natural planner, life will be much easier if you divide and conquer. Plus, others need to contribute to the planning.

One person can sort through flights and hotel deals, the group food expert can be in charge of picking restaurants, and a fashion-obsessive friend can research weather-and culture-appropriate options for your packing lists.

If someone in the group has a great sense of direction, let her be in charge of guiding the group on the ground. That is often the person who will volunteer to do the driving if you rent a car.

Have another friend who likes art? She can find which galleries are must-see.

Pick Your Destination

I have been traveling with a small group of friends for almost two decades. It is always fun to pick your destination!

Everyone runs through their imagination about all the places they would like to explore.

Here’s a great little book to help with research: The Travel Book: A Journey Through Every Country.

Then we have to get real with it when we consider not only the destination but our budget. The critical thing to remember is the group budget and the main types of activities people want to engage in.

Once you agree on these two things, it becomes easier to find that perfect destination!

There are a few more things to consider about the location. I found this Green List on Conde’ Nast for your consideration.

First, decide if you want to leave the state or not. Do you want to leave the country? Is air travel within your budget? How about a car rental?

Don’t forget the amount of time it will take the group to arrive at the destination. If you’re short on vacation days, picking a place that’s halfway across the world might not be the wisest choice.

Book Travel & Lodging

Since the group has made the big decisions of budget, dates, and destination, it’s time to book travel and lodging.  

We research where are the cool neighborhoods; where are most of the things we want to see?

Then, we search for lodging near our activities. Once we have this information, we can start looking at the ratings, stars, and reviews of the properties.

One of the benefits of traveling with friends is that you can share the cost of accommodations.  When we find a hotel, we usually book it on Booking.com – they have the most flexible cancellation policy!

We often decide on a large home for domestic trips. We shop on VRBO like we’re browsing for clothes, making wishlists of places to consider.

Once we find a fantastic property, we start digging deep into the reviews and looking closely at the photos. We’ll Google the town it is located. I recommend booking directly through VRBO because it has fewer fees and more flexible cancellation policies than Airbnb.

Enjoy Your Trip!

Plan your trip so you can enjoy yourself. You don’t have to plan out every day. I recommend planning out a few day options.

Having a few scheduled activities can act as an anchor and give the group something to anticipate.  Perhaps activities that need to be booked ahead of time, like ziplining or helicopter rides.

Trip Advisor is a great tool to pull suggestions. If you don’t want to DIY (do it yourself), please consider one of our recommended Travel Advisors to put it all together for your group.

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