Things To Consider When Planning Your First Trip With Your Boyfriend

Traveling is supposed to be an enjoyable experience, no matter who you’re with — but it also has the potential to be extremely stressful. You’re dropping a lot of money and using up valuable vacation time, so when unexpected things happen, it can be frustrating. Add a semi-new relationship to the mix, and the potential for a fight or two is high. But at least, for better or for worse, you’ll end up learning a lot about each other!

  1. Are you both envisioning the same type of vacation? Maybe you’re looking forward to lying on the beach with an endless supply of strawberry daiquiris, but he plans to sign up for every activity the resort has to offer. Either you both compromise on your ideal vacation vision a little bit, or you’ll end up only seeing each other every night when you go to bed.
  2. How do you handle long travel times? Whether you’re driving, flying, or taking some other method of transportation, it’s good to know how you both handle the tediousness that is traveling long distances. Some people have no problem alternating between napping and reading, while others go stir crazy without constant stimulation. Not that you should avoid going on trips together or anything, but it’s good to know what you’re getting yourself into when you book that 22 hour flight to Australia.
  3. What’s your budget? Needless to say, it’s probably not the best idea to go on an extravagant trip that only one of you can realistically afford. You have to be comfortable communicating your financial limitations to each other in order to make decisions you’re both comfortable with, or else there might be resentment once those credit card bills come in.
  4. How will you split expenses? If one of you is willing to splurge on a slightly nicer hotel, and the other person is responsible for food and drink purchases, than great. As long as you talk it out and agree on a plan beforehand, there shouldn’t be any surprises.
  5. Alone time will be hard to come by. If you don’t already live together, than a trip where you stay in the same room, share a bathroom, and eat every meal together might be a bit overwhelming. You might think that sounds fantastic, but just wait. By the time you get home, you’ll be dying for some time to yourself.
  6. You don’t have to do everything together. Since there are certain parts of your trip you’ll definitely be spending together, it’s okay to plan a few things to do on your own too. Take a walk on the beach solo every morning, and don’t be afraid to tell him when you need some me time. Chances are, he’s thinking the exact same thing.
  7. Are you ready for him to see all your weird habits? Ideally, by the time you’re taking a trip with a guy, he’s already seen what you look like with no makeup, and knows that you talk in your sleep sometimes. But if there’s anything he hasn’t seen yet, he’s about to, so hurry up and get comfortable with that.
  8. Can you both leave work at home? Or will one or both of you be constantly checking your emails, making long distance calls, and generally not relaxing? You’re supposed to be enjoying each other’s company, not obsessing over what you’re missing at work. If you can’t stand to take a vacation, then don’t go on vacation.
  9. All booking decisions should be mutually agreed upon. That way if something doesn’t turn out perfectly, no one can really be blamed. Or if it turns out to be the best trip ever, you can both take credit for being fantastic travel companions.
By day, Courtney is a digital marketing copywriter living in Toronto, Canada. By night, she's a freelance lifestyle writer who, in addition to, contributes regularly to, IN Magazine, and SheBlogs Canada. Want to chat about relationships, Stephen King or your favorite true crime podcast/documentary/book? She's on Twitter @courtooo.