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A Checklist For Planning Travel With Your Best Friend | The Pros And Cons Of Travelling With Your Best Friend | Plus, the Top 10 Places To Visit When Travelling With Your Best Friend!


An overseas trip can make – or BREAK – your friendship! Tips on how to avoid this happening to you!

You are long overdue for a holiday. So you are planning the trip of a lifetime with your best friend and it’s going to be amazing, right? Maybe not!

Travelling the world with your best friend is super exciting! But there are definitely some things to think about before you set off. Solo female travel is on the rise and there’s a reason why it is growing in popularity. As women, solo travel adventures play an important role in our self-development. Travelling solo forces you to become more confident and comfortable in your own company. Ultimately, that also makes you a better person! But there are definitely some lessons to be learnt from travelling with your best friend as well!

Best friends are awesome! Usually, they want to do all the same things that you do and have similar interests and hobbies. This is what forms the basis of many of our strongest friendships.

We tend to spend all of our spare time with that one person that just ‘gets’ us! Whether they be our partner, our best friend – or both! At home, besties share conversations over coffee and a glass of wine over dinner! You celebrate birthdays and attend parties or events together. You go shopping and may even go on a road trip or spend a weekend away. So it only seems natural that you should set off to explore the world together too!

Sharing new experiences when travelling with your best friend can be amazing! But travelling with your best friend certainly, has its challenges too.

You may be best friends at home and think that you know each other inside and out. But you never really know someone until you travel with them! (Or, in my case, until you start planning your first overseas trip together. As we didn’t even make it on to the same plane!)

I’ve now learnt (the hard way!) that best friends fallout when travelling all of the time!

It happened to me quite a few years ago so I’ve moved on from it now. However, recently two friends that I work with set off on an adventure together and returned on separate planes! I was shocked at first, however, then I started discussing it with other girls in my life. It turns out that most of them had similar experiences or knew of friends who had fallen out when travelling.

Suddenly, I realised that the curse of the best friend fallout during overseas travel is actually a thing!

If only I had realised that earlier, I may have been able to save my friendship! In all fairness, people probably did try to warn me. But my best friend and I did everything together at home, so I really didn’t think it would be an issue. Yet when my bestie suggested a trip to the USA I was hesitant from the get-go! This is when I should have spoken up. Yes, the USA is awesome but I’d been to California before (several times, for work). So I was only interested in travelling America if I meant I could see more of it!

What really lets best friends down is a lack of communication during the planning stage.

When my best friend and I started discussing our trip both of us were on a budget. So when cheap airfares went up for sale we grabbed them! The problem with that was that we hadn’t agreed on where we actually wanted to stay. Or, decided all of the things we wanted to do on the trip! Having travelled to Europe previously, I knew I would prefer a trip where I would get to see as many cities as possible. I wanted to spend one or two nights in each city and see as much of the country as I could cram into two weeks! Whereas my best friend wanted to save money on travel fares, visit a few cities and spend longer exploring them.

Through the planning phase, it can become (glaringly) obvious if you have very different travel styles!

Neither of us was right or wrong. We just wanted different things from the trip! So after not being able to reach a compromise, you might assume that we had a massive falling out one day. However, in fact, we literally just stopped speaking to each other – for months! Eventually, I realised that the trip had cost us our friendship. There was no way we were going to be able to spend four weeks in each other’s company!

Fortunately, fate intervened somewhere along the way.

The flights we had booked were cancelled. So I rescheduled my departure by a few days. We both still went on the trip (separately) without having to be stuck next to each other on the plane in awkward silence for 13 hours! I ended up joining a tour group and split my trip up to be able to spend two weeks travelling Mexico as well! And I am so glad I did, as it is still my favourite of all of the countries that I have visited so far! But it still would have been nice to share the adventure together!

It took years for us to get over it. But I’m so happy that we have now finally managed to fix our friendship!

I guess we have both grown up a lot since then and I’m glad we could put it behind us. Ironically, we had planned the trip to celebrate our birthday (as my best friend and I were actually born on the same day…cool huh!). I’d always loved sharing the celebration with her, so each birthday that followed was always a little sombre. However, today we are celebrating our birthday together, in my home state of Queensland! My bestie turns thirty today and I am so happy that I can be here to share it with her! I’m also writing this post as a toast to her and an apology for the trip that we missed out on all those years ago.

We now have a closer bond than ever before and we are even starting to discuss another holiday! Next time, though, we will be very clear from the beginning on what we both want to get out of the trip!

I have since travelled with other friends, including a girl that I used to work with in my previous job. She and I had not seen each other in quite a while. So we made plans to meet up overseas on a volunteer trip to Laos. We spent two weeks there working in an elephant conservation sanctuary. Plus we also taught English in a local school. The trip worked out perfectly, as volunteering was something we had both always wanted to do!

I also took a vacation with a friend who I regularly explore to Bali with. She is a Flight Attendant as well and we travel together all of the time.

We had an amazing week together, so I’m not saying that travelling with best friends can’t be done. Just take the time to be sure it won’t cost your friendship! The best friend fallout can be avoided by making sure you want to do the same sort of things before you book. Plus, you both need to be flexible and willing to compromise a little before you commit to taking the trip together!


Avoid the Best Friend Fallout with Proper Planning BEFORE you book!

1. Decide Where You Want to Go! Discuss which countries you want to visit, which cities you want to see and how long you want to spend in each.

2. Decide When You Want to Go and How Long For!

3. Set A Budget. (Need help? Get my free Budget Planner here!)

4. Discuss Flight Options and Prices.

5. Decide on what type of Accommodation you prefer.

6. Discuss Sightseeing ideas! What Do You Want to Do and See?

7. Be clear on what you want to get out of the trip and Be Prepared to Compromise!


Planning an overseas adventure with your best friend? I thought I’d suggest some things to consider which may to help you decide whether or not you should, in fact, go it alone!


1. You have someone to sit next to on the plane!

2. You can save on accommodation by sharing a room.

3. You have someone to go for a drink with (and to help you find a cab at the end of the night when you’ve both had a few too many cocktails!)

4. You can take selfies together and you have someone to be your personal photographer.

5. And most importantly, you have someone to share the incredible experiences with! The memories you make during overseas travel will make your friendship even stronger!


1. You may have to put up with your best friend being extremely irritable at the airport. Especially when you are both suffering jetlag and absolutely exhausted!

2. If you share a room, you are literally going to have to live in each other’s company for the entire duration of the trip! (Unless of course, you are willing to go your separate ways during the day, or even just take a time out for a few hours. Which I would highly recommend!).

3. It can sometimes be more difficult to meet fellow travellers when you are travelling with a friend. Especially if you friend expects that you will do EVERYTHING together!

4. If your best friend is anything like me, they will literally take a million photos of absolutely everything!!!! Which can be annoying, I know! (#sorrynotsorry This blog would not exist otherwise!).

5. An overseas trip can make or break your friendship! Make sure that you want to travel to the same places, see the same sights and share a similar travel-style preference before you book!


1. Disneyland.

Why? Because it’s the happiest place on earth!

2. Coachella (or Tomorrowland, or any major music festival!).

Why? Because festivals are more fun with your friends.

3. Route 66!

Why? So that you can channel your inner Thelma and Louise!

4. Las Vegas.

Why? Because what happens in Vegas stays in Vegas!

5. New York City.

Why? So that you can do the “Sex and the City” tour together!

6. Miami.

Why? Miami has the most amazing VIP nightlife and the clubs can be hard to get into on your own!

7. LA.

Why? LA has so much to offer. I enjoyed it on my own, but would love to go back with my best friend!

8. Cancun.

Why? It’s party central and the clubbing scene is lot more fun with your best friend by your side! If you are on your own though, you can always just join in the congo line at Carlos’n’Charlies!

9. Acapulco.

Why? It’s amazing, but it can be a little dangerous on your own.

10. Bali (or any other tropical island).

Why? It’s a hotspot for Honeymooners and young families. So if you are going it alone it can be hard to meet people. Personally, I love the time out! But if you don’t enjoy ‘me time’ you may get a little bored if you don’t have a boyfriend or best friend by your side!

Have you, or any of your friends fallen victim to this curse? What are your tips to avoid a best friend fallout? Perhaps you have some other recommendations? I’d also love to know where you would love to travel with your bestie! Please share your suggestions by commenting below. Plus, you can also discuss this with the DSS Tribe in our Facebook Group.

1 Response
  • Paula Maree
    25 . 07 . 2017

    Be the first to leave a comment! I’d love to hear from you! x

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