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14 Important Considerations Before You Travel With Friends

14 Important Considerations Before You Travel With Friends

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Mark Twain said it best when he said: “I have found out that there ain’t no surer way to find out whether you like people or hate them than to travel with them.” With solo travel becoming so popular these days, I wanted to share some insight about how to travel with friends the right way.

I’ve heard my share of nightmare stories from others about how both vacations and lengthy friendships have been ruined because of a trip together. That being said, I’m still a huge advocate of traveling with your besties!

Whether it’s the 5 week trip I took through southeast asia with my best friend or the numerous voyages with other couples, I’ve had a lot of great experiences.

I’ve done Mexico all-inclusive resort vacations with both family and friends a few times, friends ski trips to the mountains and most recently, I organized a 10 person friends trip to Las Vegas. 

A lifetime of awesome memories have been made by sharing my travel experiences with the people I love.

However, I won’t lie; each of these trips have come with their own unique hiccups and challenges from traveling with others. But, I’ve learned a lot from these experiences. 

The biggest lesson I’ve learned is that when it comes to traveling with friends, I approach it from the perspective of vacation versus travel.

There is a difference.

I will go on and enjoy a vacation with friends, but usually only travel with my partner. It’s a lot easier to be less stressed and worried about doing and seeing everything if you consider it more of a vacation style trip instead of an immersive travel experience.

Let’s get into the reasons why you should travel with friends, things to consider and tips to make sure everything goes smoothly!

two friends with their backs to the camera hold their arms up giving a peace sign to the red bridge

Disclosure: This post contains some affiliate links. Meaning, on certain links I may receive a small commission if you make a purchase. I only share products and services that I know, love and trust.

The Pros of Travel with Friends

There are so many great reasons why I still love traveling with a group of friends. Here they are:

It’s Cheaper! 

You can share rooms, taxis, ubers, rental cars, everything. For example, when I was traveling in Vietnam with my girlfriend, it was cheaper for us to get our own nice room and share a king size bed than to each pay separately for a hostel bed in a room with 8 other beds. 

Adding to my above point, you also open up the possibility of more accommodation options.

If you’re traveling in a larger group, you now open up the option of renting a house or a 2-bedroom condo with full kitchens and maybe your own pool. When it’s just 2 people it’s hard to justify the costs of getting something bigger. 

And if you’re afraid of Airbnb rental nightmares, I’ve got 12 essential tips to finding the perfect Airbnb (or other vacation home rental) every time.

New Places and Experiences

When you travel with friends, it opens up your possibilities to go somewhere you might never visit. I once spent a week in Louisiana and Alabama with some friends.

These southern states had originally been far down on my travel bucket list. But we were invited by some friends who were headed down for a BBQ competition.

Knowing we could split accommodation and rental car costs made it a great value proposition. So we kept our eyes out for a great flight deal and made the trek down south.

Quick Travel Pro Tip: My go-to flight deal site is Skyscanner. I love using this site because it finds and compares all the best flight prices. It provides suggestions about where you can save money if you’re flexible with your schedule.

You or your spouse might get to try things on vacation that you would never otherwise get the chance to do.

I never would have got to try the Alligator Cheesecake in New Orleans if I was travelling solo!

For example, if you’re an avid skier or snowboarder and your spouse isn’t, you may never go on a ski trip together when it’s just the two of you.

But with friends, it’s a lot easier to split up during the day and still do the things you each want to do. Like one of you goes skiing with the others, and one of you does a spa day with the non-skiers. 

Also, when you travel with friends, you’re more likely to go to restaurants that you wouldn’t normally try if your spouse is usually a picky eater.

For instance, my friend’s husband isn’t very adventurous when it comes to food, but she knew that I was. On a trip to New Orleans we picked a restaurant that served the famous Alligator Cheesecake.

Because my friend knew I would split it with her, it wouldn’t be a waste of an order. Plus, when there’s a group of you, you get the opportunity to try more items off the menu.

Built-in Photographers

One of the things that sucks about traveling as a couple is that it’s hard to get nice couple photos. You’re limited to selfies or asking a stranger to take a blurry photo of the two of you.

Some people feel awkward asking for a photo. Some are afraid that their camera will get stolen or that they’ll get a mediocre photo at best. By contrast, when you’re with your friends, they can snap photos from every angle.

Plus, you won’t feel like a princess for asking them to do a re-take. Do it for the ‘Gram am I right?

Plus, you know when you’re back home from your vacation and you realize that you didn’t get a picture of ‘X’? There’s a chance your friends may have snapped a photo and you can swap pics and have double the photos and double the memories! 

seven friends waving their arms and smiling with the bright colored city lights behind them

You Become Closer

Contrary to some of the horror stories I’ve heard from others, you actually can become closer and better friends!

Traveling with friends not only encourages you to spend long quantities of time together, but you’re doing it in a fun and relaxing (mostly) atmosphere where you’re experiencing new things together.

I mean, nothing brings friends closer together than cheering each other on to eat a chocolate covered scorpion on the streets of Bangkok or getting an impulsive matching tattoo in Phuket! 

The Cons of Travel With Friends

While taking a vacation with your besties can make for some awesome memories, there are a few perils of adventures with your amigos

One of the biggest downsides is that you might not get to do everything you want. When you’re with a group, it’s hard to keep everyone on the same schedule, same budget and same itinerary.

Some people want to sleep in, others want to be out of the house at the crack of dawn. And the larger the group the harder this becomes. 

This makes it harder to plan your trip to satisfy everyone’s interests. Things get a little more complicated when you travel with friends, especially if it’s a large group. Dinner reservations become essential when you’re with a group of 10 versus just you and your travel companion. 

And yes, while vacations with your pals can bring you closer together, you can definitely become sick of each other and get into situations that ruin friendships.

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My Best Advice and Tips About How to Travel With Friends and Make the Best of Your Vacation 

All that being said, I’ve learned a lot on my trips with friends over the last few years. Here are the most important things to consider when you’re planning to travel with friends. 

Be Direct

Bring things up with them before your trip. If there are certain quirks, qualities or characteristic traits about your friend(s) that you find a little annoying, it will be worse on the trip. Address it first.

Plan Ahead

Build your itinerary before you go. Make it fun, go out for dinner or drinks and get excited about the trip together!

I wrote a comprehensive post about all the great tips, tools and resources I love to use to keep myself organized when planning any trip. It will help you stay organized and avoid going insane! 

Consider testing out a short weekend getaway to make sure you’re compatible travel partners.

The Calculated Traveller suggests a trial run and other tips here.

Set up a group chat before you leave or as soon as you arrive. This way when people get separated it’s easy to communicate with the whole group.

Phones always seem to die when there’s only one or 2 people who have the numbers of everyone in the group. Set Up a group chat and commit to using it while you’re on your trip.

a group of people eat dinner at a long table

It’s great for when you’re staying in different hotel rooms and you want to let people know when you’re headed down for breakfast or to the pool.

One of the most common things that causes stress when traveling with a group of people is when one person gets left out from a plan because they weren’t part of a conversation. Include everyone in the chat so everyone gets the same messages. 

Book services like hotels and car rentals before you go. This outlines the biggest costs up front so that everyone knows what to expect.

When booking your accommodations, VRBO is one of the best platforms to use when you’re traveling with a group of friends.  With VRBO you can save travel boards and ideas easily with the others who will be traveling with you.

And now has a huge inventory of guest houses, villas and resorts that are perfectly suited for a group trip.

Manage Expectations

It’s important to identify everyone’s must do’s and then leave the rest of the itinerary plans as options. This will eliminate or minimize negativity on the trip if someone doesn’t get to do something they wanted.

And this will also help avoid getting sucked into something you didn’t really plan on doing. 

Schedule Your Own Time

Build in alone time on the trip away from the other couples or friends. If you’re traveling as a couple with other couples, you’ll definitely want your own time together.

If you’re solo with a few friends, it’s equally as important to schedule alone time with yourself away from others. It helps keep the peace. 

You Might Also Be Interested in: How to Tackle Your Pre-Travel Anxiety and Make the Most of Your Trip

Choose Wisely

Try to travel with couples who have already traveled together. If you’re traveling with a new couple that hasn’t taken a lengthy trip or vacation together yet…abort!

This is almost always disastrous. We all know that traveling with your spouse can be much different than your everyday life at home; this is something many couples don’t realize until they actually go on a trip together. 

Determine Budgets

You’d be very surprised to find out how cheap frugal people are until you travel together! Decide how you’ll be splitting costs before you travel. It’s a lot easier to have everyone on the same page before you leave.

It can be awkward asking for someone’s half of the money after the trip. Especially if you do happen to become sick of each other after you return home. 

four friends wrap their arms around each others' back at sunset

Know Your Travel style

It’s important to figure out what style of travelers each of you are. Some are more adventurous and outdoorsy, some will only stay in a 5 star hotel. Never assume someone’s travel style based on their lifestyle.

These can be quite different! When you travel with friends this will become apparent early on in your trip. So, it’s best to make sure you’re all relatively close in your travel styles. 

The Power of Snacks

Usually when you’re travelling as a group, you want to see and do as much as possible. Or, it might a busier trip than normal because there’s more of you to do more things.

Keep snacks with you, because chances are, there’s going to be at least one of you who gets hangry. Bring snacks, and plan food stops, because people will get hungry at different times. 

Speak Up When You Need To

Don’t be afraid to speak up and say something if you’re not feeling well or if you’re uncomfortable about something. On a group trip, you may not want to seem like you’re a party pooper.

But don’t be afraid to tell the group. The good news is that if your spouse still wants to do the activity, they can still go while you relax back at the hotel or on the beach. 

Technology is Your Friend

Chances are high that you’re going to be using Uber or Lyft as your main sources of transportation. Make sure everyone has the app(s) downloaded and ready to use so that you can split fares easily.

It’s a good idea to do this before the trip, in case yourself without WiFi and can’t download it. Or if someone’s phone dies you can still grab a ride without delay! 

And if you want to guarantee WiFi anywhere you are at all times, consider buying or renting a pocket WiFi device like Skyroam.

It’s perfect for situations when the airport WiFi sucks or when you’re on a road trip trying to make travel plans.

Take advantage of apps to make your life easier. For instance, you can use Travelchime when you’re planning your itinerary together. This platform allows you to collaborate in real time with your friends.

You can leave notes or updated information so that the entire group has access to it. 

That’s it, amigos! Grab your pals, book a trip, head out on an adventure and have the time of your life. Because:

In life, it is not where you go, but who you travel with

Charles Shultz

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Johny Marks

Thursday 17th of October 2019

Hey Alyssa, I guess while travelling with friends renting a car with more than 7 seats is the best option. You will save on fuel and logistics if you rent one car instead of driving two or three. And you will have the chance of joking and laughing all together while you are travelling. Great Post.

Thomas Peterson

Thursday 5th of September 2019

I like the tip you made about travelling in a group for better accommodation benefits. I've been wanting to go on a trip before the end of this year. Maybe I should invite some friends and help pay for a much fancier stay.


Thursday 5th of September 2019

It really does help open up your options for a nicer or bigger place. I hope you can get some friends together and make some memories!

Emily Adams

Saturday 17th of August 2019

It's so nice when you're able to find compatible travel friends - I have only one or two that I can go on long trips without getting too irritable. These are great things for everyone to consider!


Monday 19th of August 2019

Thanks for reading! It's definitely a challenge to find people you can travel with long term, but when you do, it's pretty awesome :)

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