What You Should Know Before Vacationing With a Friend

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Vacationing with a friend can be very rewarding and the memories can last a lifetime, but it can also go the opposite way and you end up resenting each other before you’ve even completed the vacation. Before you decide to travel with a friend, be sure you’ve put enough thought into whether you will make good travel partners, or it might wreak havoc on your plans.

I love to travel. Thinking up new vacation spots is another hobby of mine. However, I don’t have a lot of people in my life who share this joy, so I often end up asking friends if they’d like to travel somewhere with me. While I’ve had this turn out great many times, it’s also gone awry a few times.

traveling together

Instead of blindly asking a friend to travel with you, we recommend going through a vetting process and sharing with any possible travel partners how you like to travel and what bothers you most while traveling. Asking and answering questions will help you find the right travel partner.

How Things Can Go Awry

For instance, a few years ago I found a friend who wanted to travel to one of my dream destinations with me. I was very excited to have her along, but we hit our first snap on the very first morning.  I was exhausted from the journey, and in a deep sleep, when I heard the words, “Wake up! It’s time to get up!”. At first, I thought I must be dreaming. I am on vacation. Who in their right mind is bothering me about getting up.

While this annoying sentence is being repeated and light is beginning to fill the room, my mind went racing through the reasons this was happening. Let’s see, I decided where to go, I picked the dates… and then I asked a friend to come with me. Yep, that was it. I asked a friend to come along.

This friend and I had never traveled together before, and we didn’t discuss our travel habits and wishes before we went. We just assumed everything would be fine. We didn’t talk about wake-up times, bedtimes, meals, tours, likes, dislikes before we left on this dream trip.

In fact, we don’t even really know each other that well.  I just assumed we’d travel well together because we’ve done lunch, dinner, happy hour, shopping and a few other things together and it was always fun and carefree. It just seemed a natural fit for us to travel together.

Now here I was, being woken up early on the first day of my vacation, already feeling like it was a  mistake. How did we get to this point?

Was it a Mistake, Vacationing with a Friend?

Rude wake up calls while on vacation can be very annoying
Rude wake up calls while on vacation can be very annoying

This is when I went into #savemyvacation mode. I took a breath, counted to 10 and said those dreaded words, “Girl we need to talk”. I tried to replace the annoyance in my mind with the things we should have discussed before embarking on our girl’s vacation.

It would be imperative to the remainder of our vacation to have this talk and get everything out in the open before it backfired on us.

Instead of getting yourself into the situation I was in, I highly recommend following a few guidelines to make sure you and your friend make a good fit for traveling together. Even just discussing a few important details will have a major impact on your vacation.

How to Prepare to Travel With A Friend

1. Have a Pre-Trip Discussion

Traveling with a friend who you’ve never vacationed with before can be difficult. It’s hard to tell just from every day activities if you will actually be compatible travel partners. The best way to ensure a successful trip is to talk over your expectations and get on the same page.

Here are a few things you should ask and discuss before vacationing with a friend:

  1. What are your sleeping habits? Do you go to be early/stay up late?
  2. What time do you like to wake up?
  3. Do you snore and/or does snoring bother you?
  4. Are you a planner or spontaneous?
  5. What is fun for you? What things do you try to avoid?
  6. Does it take you a long time to get ready?
  7. Does smoking or drinking bother you?
  8. Do you want to start out our days together or do things separately?
  9. Are you ok with doing some things apart and meeting up later?
  10. Are you an adventurer or relaxer?
  11. Do you like to spend a lot of time taking photos along the way?
  12. Do you have any food restrictions?
  13. Do have any medical issues that I should know about?
  14. What’s your budget for activities? Are you on a shoe-string budget or can you splurge?
  15. Do you like to un-plug while on vacation or need to stay connected for the whole trip?
  16. Who do I contact in case of an emergency?

This list may seem silly, but information is power and can help you avoid the vacation nightmare that I found myself in. You can use this list like a take out menu, pick the ones you like and or make your own questions. Just make sure you do it.

travel planning

2. Planning a Vacation With a Friend

For many people, planning is the first stage, and often the most important part of a vacation. However, I’ve quickly found that not everyone wants to plan a vacation in the same way. Some people like to be spontaneous and feel that a schedule is restrictive. Others like to plan every second.

Which of you will be doing the planning? It’s important to iron out exactly who will do the work and how much planning is required to make you both happy.

One of the major sticking points in planning a vacation with a friend for me has been if one person ends up doing everything while the other just goes along for the ride. That might be a totally fine way to go about it, but if you haven’t discussed that in advance, it can lead to negative feelings.

3. What’s the Budget?

Another planning aspect of vacationing with a friend that is very important is the budget. Before you even leave home, the subject of money can put a damper on things. Where will you stay? Will it be budget, mid-level or luxury? If one person wants to stay somewhere nicer that the other can’t afford, it can be a big problem. 

Where will you eat? I went on a vacation with a friend to Hawaii. She wanted to eat in for at least half of the meals and had brought microwavable oatmeal and ramen to eat. I wanted to enjoy the local restaurants and stop for drinks at bars.

If we had considered this before leaving, we could have come to a compromise beforehand that would have saved us a really uncomfortable fight about eating out.

4. What About Activities

Traveling with a friend can be a lot more fun than going there by yourself. For one thing, you’ll have someone to engage in activities with you. However, not everyone has the same idea of vacationing when it comes to activities. One person might want to lay on the beach all day, while the other wants to hike, bike, and go shopping.

It’s okay if you want to do two different things, but if you go in thinking that you’ve got a partner to hike with and they don’t want to do it, you might end up very disappointed. Always talk about your level of activity, what you feel about spending time alone, and how much time you want to spend together. 


So what happened to us, you may wonder? Well we went to breakfast and had the talk. Once the air was cleared, the rest of the week was awesome! We hit some snags along the way, but the talk helped us laugh our way through, gather memories, have fun and survive the mishaps.

Even though I didn’t do the pre-trip fact-finding mission, we found a way to move forward. Now I know. I will always ask my traveling companion who they are so I can be who I am.

This is a guest post by Niki Deanda, who frequently travels for work, with and without coworkers in tow. She loves to see the world and experience new places, and she has a lot of great advice for people who are considering traveling with a friend for the first time.

Be Prepared For Travel

Planning is the most important part of any successful trip. Do it the easy way:

🧳 Travel Packing List | ✔️ Why You Need Travel Insurance | ✈️ What to Do Before You Leave Home


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Before vacationing with a friend, asking a few questions will help alleviate any issues that might arise.
Before vacationing with a friend, asking a few questions will help alleviate any issues that might arise.
What You Should Know Before Vacationing With a Friend

21 thoughts on “What You Should Know Before Vacationing With a Friend

  1. Carmen's Luxury Travel says:

    Yes! This is so important! I can’t travel with some friends… and they’re close friends! Thanks for sharing 🙂

  2. Milosz Zak says:

    I’m doing a trip in July with a friend, and I expect it will be a real test of everything. I’m usually a trooper and can withstand any discomfort, but it is so true that some people are just made for the beach. I plan to do a ton of hiking.

    • Laura Lynch says:

      Right – you might be able to withstand it, but is it necessary to sacrifice if you can get some things out of the way before you even go?

  3. Holly says:

    Really important to do, even with a significant other before traveling together for the first time! Best to get on the same page about expectations. It might seem like an uncomfortable conversation at first, but you’ll be happy you did it!

  4. Michelle W says:

    Interesting points.. I am going on a trip this summer with my best friend of 25 years, and this is our first international trip together. We know each other SO well that I feel like we’ll be fine.. but then again.. Hmm. Guess we will see!! 😀

    • Laura Lynch says:

      There’s no harm in having “the talk” before you go, just to make sure you’re both on the same page, right?

  5. Aisha says:

    This is food for thought. Thanks for sharing this. I am planning a two week trip with a friend and that will be the longest time we have spent together.

  6. Sharmistha | That Girl's Life Stories says:

    Haha – this post is so to the point..Loved it.. I’ll definitely consider this when I travel with my friends 🙂

  7. Castaway with Crystal says:

    Definitely some very good tips in there. I honestly prefer travelling alone but it’s nice to have a friend come along every now and then (but make sure you get alone time, honestly!). Thanks for the post.

    Crystal recently posted… Budget Guide: Japan

  8. Theresa says:

    In college I did the travel with friends or groups and I’d much prefer the solo route or traveling with a boyfriend. I like the inherent freedom that comes with it. Plus, I can sleep in as long as I want. 🙂

    • Laura Lynch says:

      It’s definitely easier to travel alone or with a boyfriend. You don’t have to plan around someone else’s schedule.

  9. christine says:

    It always good to have that talk. I know many people that went on vacation together and it ruined their friendship!

    • Laura Lynch says:

      I ruined a friendship like that, actually. We got on different planes and never saw each other again. It was sad to see it end that way.

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