20 Ways to Travel With Friends (and Keep the Friendship!)

No matter how well we know each other, travel with friends always has the potential to become a powder-keg of differing opinions.  Adding family into this mix can only serve to escalate the chances of an explosion!  We can’t just isolate ourselves and travel the world alone, so how do we successfully maintain our travel lifestyle and bring our friends along for the ride?

Here are the 20 best ways I have found to travel with friends so the friendship outlasts the trip!

No surer way to find out whether you like people or hate them than to travel
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Choose Your Partners

The first step in travel with friends is also one of the most important:  deciding who you want to travel with.  It’s important to be somewhat sure that everyone will get along.  This is not the time to play peacemaker!  Do everyone a favour and don’t tell everyone they’re welcome to join you if they’re not.  You may be surprised who will accept a “courtesy invite”, and throw off the entire group dynamic.

Travel will force everyone to be together almost constantly, and often in small spaces.  You’ll learn more about each other in a few short days away that the past year of occasional gatherings.  Be aware that previously unknown habits will annoy you … but yours will also annoy others!

Don’t let this warning deter you from expanding your travel group.  As long as everyone gets along on the surface, it’s much more likely that the shared experiences you’re about to share will make you closer than ever.

Pool Your Resources

While planning for your trip I’d recommend you take the opportunity to pool some of your resources.  There are things everyone needs their own supply of, but there are a lot of things that can be shared.  No need to weigh down everyone’s luggage with unnecessary duplicate items.

Here is a short list of the sorts of items that you shouldn’t need more that 1 or 2 of:

  • portable power
  • portable memory
  • international smartphone plans (share the cost)
  • camera equipment – tripods, flashes, etc.
  • maps, gps

Send Reminders

As your departure approaches it’s best to remember that the trip starts even before you even leave. This is especially true while travelling with friends. Be sure to provide reminders for any specific items your group will need to bring.

Items of note may include appropriate clothing for planned activities, weather or culture-specific items, or up-to-date travel documents.  It’s never fun to be the one person who forgot fancy clothes while everyone else goes out for a nice dinner, or to be prohibited from entering a place of worship.

Set a Basic Itinerary

Get everyone together and plan out a basic daily itinerary for the group to follow (or not).  Nobody wants a social director for the whole trip, but it’s best for everyone to known what’s planned and what isn’t.

Try to include the basic details of where, when, and cost.  Make sure everyone knows that they are all welcome at each event, but none of them are mandatory.  If there is a requirement to pre-purchase or create advanced reservations, it’s best to get a commitment from those who are interested (with payment!) prior to departure.

Travel With Like People

Although the entire group doesn’t need to be of the same travel mindset, you also want to ensure no one is being left out.  If some of you are adventurous and plan to go on a rock-climbing excursion, make sure that those who prefer to remain on the beach to soak in the sun or go into town for some shopping aren’t doing so by themselves.  Even worse, you don’t want to force anyone to feel they need to join in on an activity they won’t enjoy for fear of being left behind.

What’s Your Travel Style?

If you’re tasked with making room assignments try to pair like-people.  You’ll want to go beyond personalities and general interests and focus on lifestyle attributes.

Who are your morning people and who are your night owls?  Who wants adventure and who wants to relax?  Who wants a quick meal before heading out to an event and who considers the meal to be the event?

People will naturally be attracted to those who share common interests, so why not try to give the a head start!

To Join or Not To Join

You’ll want to plan enough of the trip to hit everything on your group’s “must do” list, but be sure to leave ample time for everyone to do their own thing as well.  I’d recommend planning no more than 1 or 2 main focuses each day.  This usually leaves time around and between those activities for everyone to do what’s important to them.  As we’ve already discussed, make nothing mandatory (unless there’s a wedding or something similar!), and don’t fault anyone for opting out of an activity … even if you consider it to be “can’t miss”.

Leave a Time Cushion

Corralling groups is like herding cats!  The larger your group, the more difficult it’ll become to get everyone out the door.  Be sure to leave a time cushion for anything you have planned.  Decide on the time you need to be somewhere and begin working backwards.  How long will it take to get there?  What time do you need to leave?  How long will it take you to get ready?  Are there additional considerations like shared bathrooms that need to be accounted for?

Whatever time you come up with, add at least another 30-45 minutes.  Sometimes even this preparation will be cutting it close.  It’s amazing how something as simple as leaving a hotel room can become the most difficult part of your day.  You’ve never seen so many sharp people forget their sunglasses, phone charger, hat, or wallet in the excitement!

Plan Some Alone Time

As much as you might love everyone in you group, make time for yourself and/or your significant other to be alone.  Vacation is a wonderful opportunity to grow yourself and your relationship, and you’ll want to take advantage.

A stroll along the beach, a special meal, watching a sunset.  Whatever it is, plan to separate from the pack and have some alone time.  You’ll be all the better for it!

Make Reservations

There are bound to be a handful of meals or activities that will being everyone together when you travel with friends.  Depending on the size of your group and your destination, it may be in your best interest to make reservations or find out about group ticketing in advance.

We have found that OpenTable is one of the best ways to pre-book dining spots for a group.  It’s a free app for your smartphone that makes dining reservations a breeze.  As for ticketed events, calling ahead may be the only way to ensure group seating or group entry.


Plan Ahead

Plan ahead for the next day.  What activities are on the agenda?  How long will you be out before returning to your room?  For example, if you’re doing a bit of sightseeing followed by an evening concert, you may want to do away with any bulky camera equipment and take a change of shirt.  If you have rented a car this is a lot easier, but you can do it without as well.

Pay special attention to weather changes, and try to be prepared for whatever your day will throw at you.

Check Energy Levels

Try to be aware of everyone’s energy levels, and especially your own.  You may want to postpone a morning hike today if half the group was our late the night before.  Beyond that, pay attention to some of the little signs as your day progresses.  Did everyone remember snacks and water for that hike?  Should you stop for lunch before visiting another attraction, or can it wait?

Staying well-fueled and hydrated will go a very long way in making sure your trip is the best it can be.

Fun for All

While planning to travel with friends it’s best to let everyone pick something they really want to have included in the itinerary.  Nobody should always be leading or following the group.  Do this to make the best effort to make sure everyone is having a great time, and avoiding any potential resentment.

Try to divide the itinerary so that each of you has a roughly equal number of activities to look forward to.  For any activities that take longer than a half-day to complete it’s best to have a consensus on within the group.  We don’t want anyone comparing their choice of a 1-hour snorkeling course with your full-day dinner-theater excursion.

Make Your Plan

Be sure you lead the way on the parts of the trip you care most about.  This is your time to be in charge.  Don’t be a drill sergeant, but take care of the planning and make sure you let everyone know what they can expect.

Find out for yourself what tickets cost, how to get there and when it’s open. Make note of any special dress-codes or cultural requirements.  Then when you drag your friends along, they don’t have to worry about all the logistical hassles and the experience will likely be enhanced for everyone.

Work on the Go

Yes vacation is supposed to be a time to get away, but these days it’s unlikely that everyone will be able to completely leave their work behind.  Whether you’re an entrepreneur enjoying the “laptop lifestyle” or an employee who needs to meet a deadline, I get it – sometimes you just need to get some work done.

Don’t take this a license to “check-in”, or show everyone how “important” you are.  If you absolutely must get some work done, only do what’s urgent, and only do it on your own time.  Wake up early or skip pool time.  Plan in advance when you are going to work and do your best not to interfere with everyone else.


Don’t Overbook

When traveling by yourself it’s easy to simply skip an event or two if you get tired.  Travel with friends adds another dynamic – one person’s optional event is another’s dream activity. You want to make an effort to let everyone feel that their choice is special, and avoid having them feel like nobody wants to participate.

Scheduling some down time allows everyone to periodically relax and recharge without forcing anyone to give up their dream activities.  How often you schedule this will depend on your group dynamic and what activities you’re participating in.  One group of friends may have no problem going 2 or 3 days of hiking before a rest day, while another group may no be willing to do more than a half day.

Make a Budget

Once again, this is an easy one to accomplish when traveling by yourself.  When you start to travel with friends you’ll quickly realize that everyone’s idea of money is different.  Likewise, everyone’s idea of which activities are “worth it” is very different.

The good news is that group travel usually helps you save money!  That said, a consensus on how much money you’d like to spend is important. Whether this is a daily limit, or an activity cost limit, it’s best to set this ahead of time.

Meals can be one of those touchy subjects.  Most people want to experience the culture and foods of the area, and everyone needs to eat, right?  Your food budget is normally one of the biggest costs of any trip, but it can also be one of the best places to save money.  Here’s a blog post about some great tips to save money on meals.

Decide ahead of time on a budget that everyone agrees to, and stick to it.

Stay Calm

Something will go wrong!

Airport delays, lost luggage, missed train connections, or some other minor disaster is inevitable.  The longer the trip, the more likely something will go wrong.  I’ve experienced my brother-in-law losing his credit card in a “bank machine” in Mexico and having to wait around all afternoon until someone came out of the booth after they magically found it.  I’ve waited for a train to come that didn’t exist causing me to almost miss boarding a river cruise (seriously, we arrived right as the ship was preparing to leave instead of 3 hours early).

Do your best to stay calm.  Keep your cool and consider carefully when to open your mouth.  Angry words said in a moment of stress can have an impact on the rest of your trip.  Nobody wants to feel they did something stupid, and no is not the time to remind them.

Share the Decisions

Do your best to share the decision-making duties.  That’s not to say you have to vote on every little thing, but make sure no one person is always making the choices while another is always left following along.  Everyone has their own opinion and is entitled to it.  If you’re really in a situation where nobody minds either outcome of a decision, just pick one and move on.

Keep in mind that this is not “your” trip, rather it’s everyone’s trip.  Act accordingly, and make sure everyone is involved in any important decision.


Enjoy your time together!

Yes, everyone wants to update their social media with all the awesomeness that’s happening on your trip.  That stroke of genius for your next blog post can come out of nowhere.  Just make sure you’re taking away from enjoying the moment by being face-down in your smartphone.  Make sure there is some designated time each day for some fellowship.  Your experiences will be enhanced as you discuss the day’s activities over a drink.  Have you ever found that you missed or forgot about something incredible that happened until reminded by a friend?  I know I have!

Treat every tip like it could be the last time you’re all together.  Eventually families, work, or life creep in.  That pact you made in university to take an annual trip together can turn into every 2 years, then every 5 … Take time to enjoy each other’s company.

Travel with friends can give us some of the best experiences of our lives.  Differing personalities and opinions can have their challenges, but these 20 simple tips will help ensure you keep your friendships and have many more awesome trips in the future!

Do you have any other tips that I should add to this list?  Post them in the comments below; I’d love to hear them!


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