← All posts

Tips for Planning Your Group’s Itinerary

An open travel journal showing a five-day itinerary and a map, surrounded by a camera, a passport, a coffee mug, and a phone displaying a group planning checklist

A well thought out itinerary is the difference between a trip of a lifetime or a trip you’ll wish you skipped out on. The reality is, you’ll have to treat planning your itinerary like a job. Especially if you and your friends are planning on spending thousands of your hard earned dollars.

Meet Up In Person

Communicating through a group chat or a video call never feels like it ever gets the job done as well as meeting up in person does. We recommend setting up frequent recurring times where everyone can meet up to keep the ball rolling. When we were planning for our trip to Vietnam and Japan we met up once every other week until our itinerary was fully fleshed out.

What worked for us was setting clear goals to be accomplished every time we met up. Here are a few examples of what we focused on each time we met up:

  • Figuring out which major cities we are visiting and deciding how long to stay in each of them
  • Booking all of our flights and accommodations
  • Figuring out transportation and booking all of our needed transportation tickets
  • Figuring out what we want to do each day

If you’re looking for an app that helps you plan your itinerary, upload all your flights and accommodations bookings and more, check out our free app that’s available on the App Store, the Google Play Store, or our web app here.

Figuring Out Everyone’s Deal Breakers

Everyone in your group will most likely have a must-see or must-do activity. However, often times it proves to be difficult to include them all into one itinerary. One person could have an activity they’d like to do on one side of the country while another person in the group might want to see a different city that’s on the other side of the country. Planning around these deal breakers can be challenging and can only be solved through compromise. Having these difficult conversations early in the planning phase makes them easier to resolve.

Divide and Conquer

Even if your group has a designated or self-volunteered trip organizer, it’s still a good idea to write out tasks and split up the work accordingly. One strategy that we used was playing to every individual’s strengths. For example, Tony in our group is a huge foodie and was responsible for finding all the best eats. Andres, who is resourceful and is good at finding great deals, was in charge of flights and accommodations. Claire, who loves nature, was our point man for finding cool outdoor activities.

Get the trip out of the group chat.

Bachelorette weekends, ski trips, family reunions, spring break. If it has a group chat, it belongs on Orbit.

Free for the whole crew. No ads, no expense caps, no paywalls.