“Never go on trips with anyone you do not love.” — Ernest Hemingway

I wonder if Hemingway learned this lesson the hard way. Traveling with friends can be the best or the worst. This is how we set up our travels with friends for success.

Before Your Trip

Talk about your travel style.

Do you like to plan out every minute of your day? Does your bestie prefer to sleep in and then get lost on the way to dinner? Talk about this before the trip. If your travel styles are really different, go get coffee and talk about how you’ll balance your different approaches.

Before this trip we had a FaceTime call with our friends, Amanda and Jeremy, which mostly revolved around what a good travel day looks like to us. We were on the same page and had a great trip.

Traveling with them was a dream because we happen to have really similar styles. We all like to do our research and make a plan for the day, but we are also open to taking detours and exploring along the way. Knowing this going in made for a smooth trip.

Make a basic itinerary.

You can get really into it and make a carefully color-coded Google doc or just loosely outline your days, but whatever you do, make a plan. Having a plan will ensure everyone knows what’s going on and help cut down on potential confusion and frustration.

Talk about money.

Who is paying for the AirBnB? Are you splitting the rental car cost? How much do you plan to spend on meals? Ask these questions well before you get on the plane.

Plan to be flexible.

Prepare yourself mentally to go with the flow.

  • If you are a planner traveling with a laid-back friend: Download a meditation or yoga app to help you relax and de-stress.
  • If you are a laid-back person traveling with a hyper-organized friend: Keep yourself organized with notes on your phone and make sure you download any apps you might need (like your airline’s app) before you leave your home.

During Your Trip

Communicate clearly what you’re feeling.

Feeling exhausted/hungry/overheated/etc.? Let your fellow travelers know how you’re feeling. Saying that you just need some sleep/food/shade/etc. will help you avoid hurting the feelings of your pals.

Give each other some space.

Even the most extroverted of people need some alone time to recharge. You’ll be able to enjoy each other’s company even more.

Tip: Springing for the AirBnB with the extra bedroom is always worth it.

Set up a group text.

This one is a bit obvious, but of course it’s easier if you all have one place to go to for communication. On our last trip we had a group Facebook Messenger chat happening and it worked well.

Be kind.

It’s always a good idea. 

Check these boxes and I think you’ll be on your way to an awesome trip!


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