Traveling with friends always seems like a great idea, whether it’s a long weekend in London, a month-long road trip around the south island of New Zealand, or a two-week stint in Italy and Spain. We all want to believe that the people we love and cherish will be great companions for such adventures, but unfortunately it doesn’t always work out that way.
No matter how close of friends you are with someone, traveling has the potential to bring out the best and the worst in us, especially when we encounter unexpected or stressful situations. This doesn’t mean you should never travel with others – traveling with friends can be an awesome experience! But because everyone has different travel styles, there are some conversations you should definitely have ahead of time to ensure your friendship remains intact by the end of your trip.
Whether it’s just you and your bestie or a group of five people you met a month ago, discussing certain issues ahead of time can do a lot to prepare you and your friends and get you on the same page before you take off. While the specific details will vary depending on the type of trip you are taking, these are some general guidelines for topics to discuss with each other to get the ball rolling.
Mode of Transportation

How are you going to get from place to place? For some trips, this may be obvious: we are renting a van for one month. But in other cases, you may not have all your transportation planned ahead of time. Maybe you are starting off by flying into a city and then making your way across the country from there through a combination of trains, buses, boat rides, etc. Are there certain forms of transportation you prefer to others? Are you willing to take a 12-hour overnight bus ride or would you rather just fly? Is hitchhiking an option and do all people involved feel comfortable doing it? Are you as a group willing to pick up hitchhikers if the opportunity arises?
Budget
There is nothing worse than feeling like you are bringing the group down because everybody wants to spend money on something that you can’t afford, so it’s good to talk about what you are willing to shell out for ahead of time. It’s ok if sometimes one or two people want to spend money on something that others don’t, but acknowledging ahead of time that this might come up can help make it a less awkward situation in the moment.
It’s also a good idea to talk about how you will pay for and keep track of group expenses – will you take turns paying for meals and hostels and just make sure it evens out? Or will you each pay only for your own costs the whole time?
Accommodation

Getting good sleep and having enough energy is paramount to having a great travel experience. Especially when going from city to city at a fast pace, traveling can really take it out of you and not feeling well-rested can add unnecessary stress. What kinds of places are you willing to stay in and how comfortable do you need to be to sleep well? Will you be utilizing websites like Couchsurfing.org or bringing your own tent for camping? Will you be staying in cheap hostels on the outskirts of town? Or are you willing to shell out some extra dough for nice hostels and hotels in the center of the city?
Entertainment
What kinds of activities are you interested in doing as you travel? Are you someone who enjoys art galleries and museums? Do you want to spend as much time outdoors as possible, hiking, bungee jumping, swimming in the ocean, or are you more into hanging out at shops and cafes in the city? Remember that it is perfectly fine to have different interests and you may occasionally end up splitting up for different activities – that doesn’t mean you won’t make good travel buddies!
Alone Time

Even for an extrovert, traveling with the same one or two or five people for a long period of time can get a little overwhelming. Know that it is ok to need a break! Talk to your friends about how you will make sure you each get enough alone time and what you are willing to do to make sure that you get it.
Will you split up and do your own thing for an afternoon? Will you take a few days apart and meet in the next city? Even if you don’t think you need alone time, it’s a good idea to make sure you get some at least every few days. Sometimes you don’t realize how much you need it until you get some space from the people you’ve been sharing every second with for the last 72 hours!
Meeting New People

When you travel alone, it’s easy to meet new people and decide you want to spend a few days hanging out with them or even going on a mini-adventure together. To me, this is one of the best parts of traveling! But when you are traveling with someone else, they may not always be as keen to add a new person to the mix as you are. Before you invite someone you’ve just met to join your group, whether it’s for a meal or a 7-day trek, it’s always a good idea to check in with each other first and make sure you are both on board.
Itinerary
Discuss how you will handle disruptions in the itinerary, or how specific of an itinerary you want to have in the first place. How willing are you to go with the flow? If you are really enjoying a city, are you ok with staying there a few extra days and removing something else from your plans? Are there certain things you absolutely don’t want to miss, or tickets you need to book ahead of time?
Create at least a rough outline ahead of time of where you will go and look it over together, making notes of what is most important to each of you and where you may have some wiggle room!
Stressful Situations
When everything on your trip is going great, life is beautiful and you feel like a whole new person who has just discovered their place and purpose in the world! But when you miss the flight you paid $600 for and every hostel in the city is booked up, things can get a little stressful and frustrating. Be aware that situations like this WILL come up during your trip and talk about how you will handle them when they do.
Do you need personal space when you feel stressed or do you prefer to talk things out with another person? How can you support your friends and keep from taking your frustrations out on each other? How will you work together to move forward and make the best of a difficult situation?
Whether you are a novice or expert traveler, this list offers some great starting points to talk over before you head out on a trip – you may even think of a few more key items that are important to you when it comes to travel. And more than likely, even with the best preparation, things will come up you didn’t even consider that will need to be dealt with or figured out on the spot.
It is simply impossible to prepare for everything, which is part of the fun of traveling! However, if you have at least given a cursory glance over this list with your travel buddies and started out with open communication, it will lay the foundation and make it that much easier to discuss issues as they come up along the road.
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