Are you ready for your first vacation with friends? Are you nervous about it? I hope so because this article will help you feel more at ease on your trip. Since this is my first post to a blog, I’m going over some important details about traveling together as a couple and the general advice for anyone who attends the same school. You’ve probably been to Hawaii, but have you ever been to the islands with friends? It’s definitely the best way to see the beautiful place. This will be a short article with tips, recommendations and ideas where you can travel with friends or in a big group of people.

These days, it’s hard for me to think about a vacation without thinking about my friends and how we met. But it was one of those moments that I’ll always remember: We were on a beach in Thailand sipping margaritas, lounging on the sand — just like an old married couple — when we heard screaming. This being our first vacation, we thought it was someone drowning at first. It wasn’t until a little later when we saw an old man running towards us holding what looked like a…goldfish? That’s when we realized that yes, he did indeed have a goldfish on his head. Press Tab to write more.

First Vacation With Friends

What You Should Know Before Vacationing With a Friend

LAST UPDATED ON JUL 27, 2022 BY LAURA LYNCH

Note: This article may have links to products we make commission from.

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.

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?

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?

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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.

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.