How to Plan a Trip with a Friend


Planning a trip can be tricky! Especially if you’re planning a trip for two (or more). The thing is, traveling with a friend can give you treasurable memories that will last you a lifetime, but it can also be very much like living with a friend: The idea sounds impossibly perfect, but the reality of it may be absolutely imperfect. This doesn’t mean that you have to travel the world solo. No, not at all. I’m here to tell you that traveling with a friend isn’t only possible, but that it can be one of the most incredible journeys you will ever venture on! Just keep in mind these 10 tips for planning a trip with a friend and you should be fine.

This piece was written with a travel party of two female travellers in mind who travelled to Amsterdam, Morocco and more, but it may be applied to larger, co-ed groups, as well!

  1. Be choosey.

Your friends are your friends for a reason. Maybe they balance you out. Maybe you you guys share similar interests. Whatever it is, it doesn’t really matter! The only thing that matters at this point is: Do the two of you travel well together? Think back to that road trip you guys took last Spring Break. Were you two constantly fighting for radio control? Or, were you singing at the top of your lungs, even though you hated the song, because you were with a great friend and the song choice didn’t really matter? The truth is, there are some friends that you can spend weeks with, and there are some friends that will drive you nuts before the day is even over. That’s just the way it is, and it isn’t necessarily a bad thing. But, a little piece of advice, don’t pick the latter to jet around the world with – even if you feel guilty not inviting her because she would’ve surely invited you. Know who will compliment your journey and don’t be afraid of being picky!

  1. Only plan a trip with someone who lifts you up.

Ok, so this kind of goes hand-in-hand with point number 1, but I think it’s very, very important to reiterate. ABSOLUTELY, IN NO CIRCUMSTANCES WHAT-SO-EVER, TRAVEL WITH A NEGATIVE NANCY. I’m serious, guys! There is nothing worse than discovering a new destination in the midst of someone who stomps all over everything positive. You know, those people who look at an extraordinary sunset and say something along the lines of, “It’s ok … I guess.” And then you look at the sunset that you once thought was out-of-this-world-wonderful and you think, “Hmm … I guess she’s right.” You want to be surrounded by people who will enhance your experiences abroad, not tear them down. So, I’ll say it again, choose a Positive Polly – or whatever the hell Negative Nancy’s counterpart is called.

  1. Decide what kind of trip you want to take before you start planning.

If you’ve been trapped in a cubicle for the past 3 months and all you want is some time on the beach, but your friend works as a lifeguard in the brutal sun day-in and day-out, and all she wants is to be as far away from the sand as possible, you’re either going to have to choose a destination that will act as a compromise or, you probably shouldn’t plan a trip together. Same thing goes if you’re more of an adventure junkie, but your friend would much rather shop the day away. Again, either find activities that act as a happy-medium or, find a different travel buddy. If you don’t, you’ll either want to kill each other from day 1, or you’ll be spending much less time together than you initially planned on. You don’t absolutely have to travel with someone who shares similar interests, but I can tell you one thing, it will make the traveling process much easier if you do.

  1. Calendars are everything!

Ok, so you guys have the same travel time off from work. Perfect! Now, it’s time to whip out the magical calendar. Plan out when and where you can meet up for the 1st day of the trip, when you have to return to your at-home-reality, and most importantly, where you want to be in between. Mentally visualize your travel plans chronologically. This visual understanding of your itinerary isn’t only perfect for the organization freak, but I promise you it will absolutely pump you up for the big day (the departure day, that is)! Be mindful of holidays and/or festivals that may be occurring where you plan on traveling. Then, plan around them! “Ok, where do we want to be on _?” “What time do busses run on _?” “Where do you want to stay on _?” This is a very vital step in the planning process. The more planned out the trip is, the more likely things will run smoothly (smoothly, not perfectly!), and the more likely the two of you will embark upon a trip of a lifetime together!

  1. Friends who plan together, stay together!

The thing is, this trip belongs to both you and your friend. No one person should be calling all the shots! Even if you’d rather take the backseat and go with the flow (which trust me, I’m all about), it pays to share the decision-making burden. In doing so, both travel companions get a say in the creation of the travel itinerary, the overwhelming prospect of choosing what activities to partake in will be balanced when handled by the two of you and you’ll both learn a lot about your future destination during the researching process. Really, it can be quite fun!

  1. If your friend has a budget, so do you …

and vice versa! Be mindful of each other’s financial situation. No one wants to sit and watch a friend eat a dynamite meal while she is sipping on a less-than-savory-budget-soup. And no one wants to lounge on a beach while her travel companion is off riding the waves with some hot tour guide on an over-priced 1 hour jet ski ride. The bigger problem: No one wants to be the friend who says, “I really can’t afford that,” especially if it means depriving her friend of something that they want to have/do. So, often times, the broker of the two is spending much more money than they want, and regretting every single second of it, which can make the trip suck! So, very important: Never base a trip budget on the person with the higher salary of the two. Unless one person is willing to shell out the extra cash for the two of you, budget as if you both earn the same income. There are plenty of ways to enjoyably travel on the cheap!

  1. Split the packing burden.

There’s no point in bringing two of everything (sunscreen, hair products, etc.). You know the saying: Divide and conquer! This is especially easy if the two of you will be sharing a room. And, if you are both the same size, you can either pack less and switch outfits during the trip OR pack the same amount you would as if you were traveling alone, but share wardrobes and have a much more varied look! So, when you’re planning your trip, be sure to decide who will bring what and then pack accordingly.

  1. Compromise. Compromise. Compromise.

Ok, guys, if it isn’t obvious already, traveling with a friend is kind of like being in a relationship! Compromise is key (along with communication, of course). This isn’t YOUR trip, this is your (inclusive of the two of you) trip. You can either plan alternating days of the journey (you plan Monday, your friend plans Tuesday, etc.) OR, break the day up (you plan the morning, your friend plans the afternoon, etc.). It doesn’t even have to be so black-and-white. Just discuss everything and figure out what works for the both of you. There’s a reason you two are friends, and if you’re close enough, you may have even gained the whole twin telepathy thing. Use it to your advantage and balance each other’s needs out.

  1. … but if you want to do different things, do different things!

Just because the two of you are traveling together, it doesn’t mean you have to be joined at the hip the entire time! Embrace your independence and do whatever the hell you want. Ok, I don’t mean ditch your friend. What I’m saying is, don’t be afraid to tell her that you need some you time, whether it’s for an hour or, maybe even a full day!

  1. Remember how lucky you are to travel together …

every step of the way! Even when you want to pull your hair out because your friend is taking WAY too long in the shower and because of it you may not make the sunrise. Just know, it’s not everyday that friends’ schedules align, especially if you’ve both already entered the work force. Cherish every waking moment together, and support each other during this once in a lifetime friendship journey!

A travel destination like a holiday cottage is truly complimented by the company you keep. Honestly, nearly each and every one of my fondest memories have been in the company of friends. They can make the would-have-been-merely-good-times amazing and the absolutely-terrible-awful-crappy-times bearable, and maybe even magically comical. I urge you, travel with a friend. Just be smart about it!