How to Plan a Successful Trip with Friends
My darling wayfarers,
I have one thing to tell you that you may already know, and several things to tell you that you might not.
First thing: there is something extra wonderful about traveling with a companion.
I have one thing to tell you that you may already know, and several things to tell you that you might not.
First thing: there is something extra wonderful about traveling with a companion.
The camaraderie is amazing. You have a built-in buddy to laugh with, to appreciate new experiences with-- new sights, sounds, smells, both good and bad. When your trip is over, you will be able to look them in the eyes and say, "Remember that time when..."
They will grin knowingly and nod, and that's all you need to know that they understand -- when so many others around you don't.
I have done all of my traveling with friends: some of it was terrible, and some of it was utterly, indescribably amazing. I have trouble imagining what it would be like to travel by myself— sometimes I think it'd be awesome and that I’d enjoy the freedom and make friends wherever I went. Other times, I imagine loneliness and isolation, and think that I’d never do it!
While I’m considering the possibilities of traveling by myself one day, today I want to pass some of my tips for traveling with other people on to you.
The following paragraphs contain my tried-and-true methods for planning and enjoying a successful trip with friends— in such a way that you will still be friends when it’s over!
Next item:
Let’s use an example: your friend is descended from Ebenezer Scrooge himself.
He pinches pennies wherever he can— he is frugal and just wants to do the free stuff. He wants to squeeze as much value from his trip as possible so he can save cash/make the trip last longer/still be able to purchase a car when he gets home!
Now, let’s say that you believe you should actually go INTO the cool buildings that you flew halfway around the world to see. And when you're in France, you want to eat at actual restaurants, not cook in the hostel's ill-equipped kitchen...
It’s clear that you are going to have some conflict. Or at least be agreeing to split up and do your own thing.
I speak from experience when I say that different budgets and spending styles can be a recipe for disaster. Both of you are destined to hate your trip and your company well before the adventure is over if you embark on it without talking about how much you plan on spending— and what you plan on spending it on. Please trust me on this. I know.
So, what to do? How do you sort the specifics out beforehand?
Pro-Tip:
Ask yourself and your friend some questions:
How much money do you want to dedicate to this trip overall? $1,000? Closer to $4,000? $200k? (Hahaha… we can wish, right?)
How much of that is going to be spent on transportation? Are all of you thinking realistically about airfare?
How much are you planning to spend on experiences— museum fees, day tours, dinner and a show? If you have trouble coming up with a realistic number, look up the fees charged for some of the things you are considering. Then budget a little extra cash for things you won't know you want to do until you see they exist. (Snorkeling, camel rides in sketchy parking lots, etc.)
How much money do you plan to spend on food? Decide how many meals you are going to eat out each day, including their approximate cost, and STICK to it. Write it down, add up the totals, and be mindful of your expenditures. Also, budget for some “cheat” days where you eat out more than usual, so no one resents the extra expense when you inevitably have to cave and get an extra meal. (Unless you are all Spartans and don’t believe in treats and/or enjoying life, it’s gonna happen.)
General example:
Anyway, the point is that we talked, we agreed, we planned, and no one ran out of money. Yay! :D
Another financial question: Does your willingness to spend money change depending on your destination? Is there anything you are not going to spend money on?
I'd like to add that it’s okay for travel buddies to want to spend money on different things— when my friends and I were in London, they all wanted to ride the London Eye. I’d already done it, and didn’t feel like paying for it again— I preferred an hour of quiet contemplation and people-watching by the Thames. As long as you communicate well with the others and understand that there will be times when not everyone is going to want to do the same thing, then you’ll be fine. Split up for the afternoon so the thrill-seekers can do the zip-line while the others sunbathe at the beach.
Or whatever. You get the idea.
I hope you’ve enjoyed this post and gleaned some ideas that will help you plan a trip with your own friends! Be on the look out for Part II: How to Travel with Friends (and not become enemies along the way)!
No one else will be able to share that sweet flood of nostalgia except someone who was with you.
Plus, you'll have a shoulder to drool sleep on during long flights. Not to mention loyal eyes to watch your luggage while you pee.
It’s a beautiful thing. ;)
I have done all of my traveling with friends: some of it was terrible, and some of it was utterly, indescribably amazing. I have trouble imagining what it would be like to travel by myself— sometimes I think it'd be awesome and that I’d enjoy the freedom and make friends wherever I went. Other times, I imagine loneliness and isolation, and think that I’d never do it!
While I’m considering the possibilities of traveling by myself one day, today I want to pass some of my tips for traveling with other people on to you.
The following paragraphs contain my tried-and-true methods for planning and enjoying a successful trip with friends— in such a way that you will still be friends when it’s over!
(By the way: that's kind of how I'm defining "successful" here-- things will always go wrong somewhere along the way. You will fail to think through a plan very well, and realize that you don't know how to get to your next airport. Or flights will get delayed or canceled. Your luggage will get lost... can't do much about that. However, if you are enjoying the company of your friends and you are getting along and thriving in one another's company, I call that a good trip.)
Anyway. Onward!
Step #1: Selecting Your Travel-buddy
Goal: Travel with someone who wants the same kind of adventure as you!
Let’s get specific, shall we?
There is all the basic stuff:
a.) You need to like this person a lot.
b.) You need to be available at the same time.
c.) You need to both want to travel. (Last I checked, forcing someone to travel with you is called kidnapping.)
Then there is something people don't always think about:
d.) You need to have the same preference for travel style.
Then there is something people don't always think about:
d.) You need to have the same preference for travel style.
What does that mean, exactly?
If you are dying for a backpacking adventure that involves hitchhiking and sleeping in a tent but your friend is picturing hotels and taxi rides, neither of you are going to have a good time! However, if both of you are yearning for a cruise, or to stay in hostels and make use of local public transportation to get around, your group has a strong chance of being able to enjoy a trip together.
It’s a good idea to probe for your friend’s thoughts on the pacing of the trip, too— are they going to cram everything they possibly can into each 24-hour period and sleep when they get home? Or are they all about wandering city streets aimlessly, taking their time to assimilate their surroundings into their soul (or something)? Do you have similar levels of comfort with striking up conversations with strangers?
Talk about it to help you get on the same page with potential travel partners.
Talk about it to help you get on the same page with potential travel partners.
Next item:
Do you and your friends have similar amounts of money to spend on this trip? Please believe me when I say you need to have similar budgets.
Money isn’t a fun thing to talk about with friends.
I know this.
It's awkward and can be uncomfortable.
But we gotta do it. Because honestly, it's more uncomfortable to be mad at your travel partner because they eat all the snacks you've bought and don't buy any to replace them. Or something like that.
Whatever you do, don’t assume from the get-go that everything will just work out… or you may end up regretting your choice of companions. If you are grown up enough to travel, you are grown up enough to talk about money and your feelings about it. :) And once you open a dialogue about it, you will find that it wasn't that bad after all.
(Side note: if it IS a conversation from your deepest nightmares, then that's a great sign that you need to not travel with this person. Seriously. If they make you uncomfortable with their reaction or approach to this subject, don't do it.)
Related to the budgeting question is this one: what do you want to spend your money on?
Money isn’t a fun thing to talk about with friends.
I know this.
It's awkward and can be uncomfortable.
But we gotta do it. Because honestly, it's more uncomfortable to be mad at your travel partner because they eat all the snacks you've bought and don't buy any to replace them. Or something like that.
Whatever you do, don’t assume from the get-go that everything will just work out… or you may end up regretting your choice of companions. If you are grown up enough to travel, you are grown up enough to talk about money and your feelings about it. :) And once you open a dialogue about it, you will find that it wasn't that bad after all.
(Side note: if it IS a conversation from your deepest nightmares, then that's a great sign that you need to not travel with this person. Seriously. If they make you uncomfortable with their reaction or approach to this subject, don't do it.)
Related to the budgeting question is this one: what do you want to spend your money on?
Let’s use an example: your friend is descended from Ebenezer Scrooge himself.
He pinches pennies wherever he can— he is frugal and just wants to do the free stuff. He wants to squeeze as much value from his trip as possible so he can save cash/make the trip last longer/still be able to purchase a car when he gets home!
Now, let’s say that you believe you should actually go INTO the cool buildings that you flew halfway around the world to see. And when you're in France, you want to eat at actual restaurants, not cook in the hostel's ill-equipped kitchen...
It’s clear that you are going to have some conflict. Or at least be agreeing to split up and do your own thing.
A lot.
And if that’s the case, why travel together at all?
I speak from experience when I say that different budgets and spending styles can be a recipe for disaster. Both of you are destined to hate your trip and your company well before the adventure is over if you embark on it without talking about how much you plan on spending— and what you plan on spending it on. Please trust me on this. I know.
So, what to do? How do you sort the specifics out beforehand?
Pro-Tip:
Ask yourself and your friend some questions:
How much money do you want to dedicate to this trip overall? $1,000? Closer to $4,000? $200k? (Hahaha… we can wish, right?)
How much of that is going to be spent on transportation? Are all of you thinking realistically about airfare?
How much are you planning to spend on experiences— museum fees, day tours, dinner and a show? If you have trouble coming up with a realistic number, look up the fees charged for some of the things you are considering. Then budget a little extra cash for things you won't know you want to do until you see they exist. (Snorkeling, camel rides in sketchy parking lots, etc.)
How much money do you plan to spend on food? Decide how many meals you are going to eat out each day, including their approximate cost, and STICK to it. Write it down, add up the totals, and be mindful of your expenditures. Also, budget for some “cheat” days where you eat out more than usual, so no one resents the extra expense when you inevitably have to cave and get an extra meal. (Unless you are all Spartans and don’t believe in treats and/or enjoying life, it’s gonna happen.)
General example:
On my last trip, we planned on eating out once a day, most days.
The hostels we stayed in provided breakfast, and we would snack for lunch or dinner— or eat a big meal in the middle of the afternoon and call it a day. We stuck to the plan, and it worked very well for us. We planned for an extra meal about every three days, depending on where we were going to be. In the highlands of Scotland, we mostly cooked for ourselves because there weren’t many dining establishments. In France, we ate out for basically every meal. Because how could we not?? It’s France, for crying out loud! ;)
The hostels we stayed in provided breakfast, and we would snack for lunch or dinner— or eat a big meal in the middle of the afternoon and call it a day. We stuck to the plan, and it worked very well for us. We planned for an extra meal about every three days, depending on where we were going to be. In the highlands of Scotland, we mostly cooked for ourselves because there weren’t many dining establishments. In France, we ate out for basically every meal. Because how could we not?? It’s France, for crying out loud! ;)
Anyway, the point is that we talked, we agreed, we planned, and no one ran out of money. Yay! :D
Another financial question: Does your willingness to spend money change depending on your destination? Is there anything you are not going to spend money on?
I'd like to add that it’s okay for travel buddies to want to spend money on different things— when my friends and I were in London, they all wanted to ride the London Eye. I’d already done it, and didn’t feel like paying for it again— I preferred an hour of quiet contemplation and people-watching by the Thames. As long as you communicate well with the others and understand that there will be times when not everyone is going to want to do the same thing, then you’ll be fine. Split up for the afternoon so the thrill-seekers can do the zip-line while the others sunbathe at the beach.
Or whatever. You get the idea.
Step #2: Creating an Itinerary
Goal: Plan a trip that everyone will love!
After you determine that you both want the same kind of travel experience, it’s time to figure out if you want to go to the same places... and do similar things while you're there!
Everyone who is planning to travel with you (including you!) needs to make a list (on their own) that categorizes their dream-itineraries into three categories:
1. Non-negotiables. These are the things that, if you are bothering to shell out a ton of money to travel, you better do, because if you don't get to, you don’t want to go. It could be a country or a landmark— Denmark or Machu Pichu. It could be an experience— you want to wander through museums and lose yourself in the art of the impressionists. It could be all three— you want to explore castles in Scotland and braid flowers into your friend’s hair. (That was one of mine, actually. There was no way that I wasn't going back to Scotland, and you'd better believe that I was going to sit someone down and braid their hair with wildflowers in the Highlands.) The point: whatever is on this list, it should be the stuff that you will majorly regret not doing.
2. Negotiables. This list is for the stuff you are willing to compromise on. In order to avoid setting yourself up for disappointment, you need to be realistic and realize that not everything on your itinerary is going to happen, especially when you are traveling with other people. They will want to see and experience at least a few things that do not align with your own desires.
Whatever you sort onto this list, it needs to be less important to you. This is the list that you and your friends will each be able to pick a few things from-- everyone will get to do a few things from their own List #2, and the rest will need to be left for another time.
3. "Icing-on-the-Cake." This list is for the dreams that won’t break your heart to pieces if they don’t happen— but will make your trip even better if they do. It’s the extra stuff— stopping to listen to street musicians, taking a selfie with the Mona Lisa, finding a foreign boyfriend, whatever. ;) It’s just good if everyone knows what kind of extra events you are hoping might occur. That way, you can all be good friends and look for opportunities to make one another's mini-dreams come true!
Now that you have your lists, it’s time for everyone to come together and look them over— and if it's going to work out, you can start putting together an itinerary! Obviously, if your lists detail a glorious Scandinavian holiday that exudes hygge, while your partner seems to be aiming for a safari in Africa, you will either need to compromise or find different people to travel with.
Or, y'know, do both. Both is good.
If your lists can be harmonized, you can begin building your itinerary around the non-negotiable list, then working in the things that are negotiable. Keep in mind that each person will likely be sacrificing some of these items, unless you miraculously want to do the exact same things! After you've gone through the first two lists, you can see how the extra experiences each of you hope for will fit in.
Pro-Tip:
Everyone who is planning to travel with you (including you!) needs to make a list (on their own) that categorizes their dream-itineraries into three categories:
1. Non-negotiables. These are the things that, if you are bothering to shell out a ton of money to travel, you better do, because if you don't get to, you don’t want to go. It could be a country or a landmark— Denmark or Machu Pichu. It could be an experience— you want to wander through museums and lose yourself in the art of the impressionists. It could be all three— you want to explore castles in Scotland and braid flowers into your friend’s hair. (That was one of mine, actually. There was no way that I wasn't going back to Scotland, and you'd better believe that I was going to sit someone down and braid their hair with wildflowers in the Highlands.) The point: whatever is on this list, it should be the stuff that you will majorly regret not doing.
2. Negotiables. This list is for the stuff you are willing to compromise on. In order to avoid setting yourself up for disappointment, you need to be realistic and realize that not everything on your itinerary is going to happen, especially when you are traveling with other people. They will want to see and experience at least a few things that do not align with your own desires.
Whatever you sort onto this list, it needs to be less important to you. This is the list that you and your friends will each be able to pick a few things from-- everyone will get to do a few things from their own List #2, and the rest will need to be left for another time.
3. "Icing-on-the-Cake." This list is for the dreams that won’t break your heart to pieces if they don’t happen— but will make your trip even better if they do. It’s the extra stuff— stopping to listen to street musicians, taking a selfie with the Mona Lisa, finding a foreign boyfriend, whatever. ;) It’s just good if everyone knows what kind of extra events you are hoping might occur. That way, you can all be good friends and look for opportunities to make one another's mini-dreams come true!
Now that you have your lists, it’s time for everyone to come together and look them over— and if it's going to work out, you can start putting together an itinerary! Obviously, if your lists detail a glorious Scandinavian holiday that exudes hygge, while your partner seems to be aiming for a safari in Africa, you will either need to compromise or find different people to travel with.
Or, y'know, do both. Both is good.
If your lists can be harmonized, you can begin building your itinerary around the non-negotiable list, then working in the things that are negotiable. Keep in mind that each person will likely be sacrificing some of these items, unless you miraculously want to do the exact same things! After you've gone through the first two lists, you can see how the extra experiences each of you hope for will fit in.
Remember that sometimes these extra things can be worked in at the last minute— and last minute plans can be just as great as the ones planned at the start of the adventure!
Ultimately, everyone’s planning process will be different, but these steps will provide some structure and help you prioritize things-- without anyone’s dreams being left out. :)
In the end, you should have the outline of a trip that everyone is excited to go on and has been able to make their own-- and everyone will have stories to tell and insane amounts of nostalgia when they get home.
Ultimately, everyone’s planning process will be different, but these steps will provide some structure and help you prioritize things-- without anyone’s dreams being left out. :)
In the end, you should have the outline of a trip that everyone is excited to go on and has been able to make their own-- and everyone will have stories to tell and insane amounts of nostalgia when they get home.
I hope you’ve enjoyed this post and gleaned some ideas that will help you plan a trip with your own friends! Be on the look out for Part II: How to Travel with Friends (and not become enemies along the way)!
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