Careful consideration typically goes into decisions such as choosing roommates, business partners, significant others, and even carpool buddies, yet when it comes to traveling with someone new we often throw all of that prepared-ness out the window. I'm here to tell you that that level of planning and communicating definitely deserves to be implemented when deciding to travel with someone, for the sake of your relationship, the trip, and both of your sanities.
Structuring a budget for your trip is absolutely essential, whether you're traveling with someone or not. While the subject of money can be a bit awkward, especially when it comes to traveling with someone you've never traveled with before, working out the nitty-gritty details of your budget and theirs will make the actual trip so much more enjoyable in the long-run, and save you both a lot of headaches.
Be upfront about your budget with your travel partner ahead of time, and compromise accordingly along the way. You may not want to spend the money to stay at a 5-star hotel, but they might want to be in a specific neighborhood - find a cheaper AirBnb that fits both criteria. Maybe one of you is exclusively taking over driving duties on the way, so the other pays for more gasoline fill-ups or snacks at rest stops. While it may feel in some scenarios that you're paying more for things that aren't exactly a necessity or fit into your budget, realize that your travel partner is also doing the same for you - where it's reasonable to do so, let it go. Enjoy your vacation, after all!
Here's the thing, standing in the security line at the airport is not the time to announce you're now a vegan. Tell your travel partner ahead of time what your dietary restrictions are if there are any, and what you're preferences around meals are. Some like to completely immerse themselves in the culture of wherever they're staying while others gravitate to what's familiar and comfortable - while there's no right or wrong here, simply understand your new travel buddy might have different preferences on style, price, or time of day they like to eat.
For example, I know I get hungry generally every 2-3 hours - while it's unreasonable of me to ask my friend to stop, sit down, and buy food or a drink with me in the middle of our jam-packed travel day, I will carry granola bars or a piece of fruit on-hand to curb my appetite but not slow down our itinerary. As much as you can, plan your food stops ahead of time (even if that means simply the morning of), so you both are able to enjoy the restaurants of your choosing.
As an introvert, the idea of spending every waking moment with someone tied to my hip, especially on a vacation, sounds like a nightmare. Even with my boyfriend, I need time to decompress and just have a quiet moment alone to regroup. While you may not relate to that exactly, recognize that your new travel partner might. Or perhaps you do feel that way and you just need a simple second to breathe - don't be afraid to say it. Traveling with someone at all is a huge undertaking, especially with someone new, so don't limit yourself by not setting boundaries when it's necessary.
While they're showering and getting ready in the morning, walk to the coffee shop and grab breakfast to bring back for both of you. Maybe you really want to check out the art gallery down the street but she wants to walk through the park - agree to separate and meet up in an hour. You can catch each other up on what went on while you were apart! To enjoy your travels it doesn't mean you are obligated to do every little thing together - and let's be honest, it'll take a lot of stress off of you both to find time alone.
Like alone time, bedtime rituals are just as sacred and important to discuss with your travel partner. Establish ahead of time what you're preferred sleeping arrangements are (ie. do you need a separate bed in a separate room or are you cool with sharing a king?), when you like to start winding down as opposed to when lights are finally off, and when you like to wake up.
Does one of you like complete, black-out darkness while they sleep? Maybe you sleep with the windows open, but they prefer A/C. Figure out where you can both compromise with each other for the sake of the trip. If spending time watching TV helps you relax before finally nodding off, but your friend prefers to read in bed, offer to stream Netflix on your phone with earbuds in as to not disturb her.
Planning the accommodations is a huge part of the trip itself, so make sure you can agree on the location, price, and style of your digs before embarking on a trip with your new friend. Some are more adventurous and perfectly happy spending multiple nights in hostels or small motels along the highway, while others refuse to sleep anywhere than in a posh hotel with plenty of amenities and privacy. Again, while there's no right or wrong here (personally, I think it depends on the location) when you're in the planning stages of the trip be sure to voice your must-haves for room and board so that you're not stuck wishing you'd never agreed to an AirBnb in the ghetto (true story, I accidentally roped my boyfriend on a trip like that on our first vacation together, and God love him, he stayed with me).
You learn a lot about someone while traveling with them, and not all of it will thrill you. Be open to communication before, during, and after your travels together, and remember to compromise. With a little preparation, you and your friend are sure to make amazing memories together, and your friendship will grow stronger!
Worst-case, you can always travel alone, too! ;)