How to Stay Organized While Planning a Trip

Lindsay Silberman shares her go-to checklist for planning a trip

Written by Lindsay Silberman

Even for those who are regular travelers, planning a trip can be an intimidating process. The logistics can be daunting: choosing the best flight times, deciding where to stay, making reservations for restaurants and activities, and trying to keep track of everything along the way. It’s hard not to feel overwhelmed as you embark on an upcoming adventure.

But travel is supposed to be fun and exciting, not stressful… right?! Ultimately, the key to ensuring a smooth and stress-free travel planning experience is staying organized. As someone who has spent more than a decade traveling the world for a living (I worked as a magazine editor covering travel for the majority of my career before transitioning to being a full-time blogger), I’ve learned a thing or two about how to navigate the process of planning a trip and how to make it feel as stress-free as possible.

Below, I’m sharing some of the ways that I stay organized in the hope that these tips and tricks might help you, too! From how to build a detailed itinerary to creating a pre-travel checklist, here are things to consider doing before your next trip.

Lindsay Silberman

Choose a destination

For those who are truly in the beginning phase of trip planning, sometimes simply deciding where to go can be a challenge. It’s important to figure out where you actually want to go and what’s logistically possible given your location, timing, and budget. 

You’ll want to keep a list of all possible destinations, and you might even consider jotting down the pros and cons of each. There are a few easy questions you can ask yourself in order to help you narrow things down. For example:

  • Are you looking for adventure (sightseeing in a busy city) or relaxation (staying put at a beach resort the entire time)?
  • How many days are you able to dedicate to the trip? (including travel time)
  • Are you open to destinations that require a connecting flight, or will you only be willing to fly direct?
  • How many hours are you okay with dedicating to travel? A half-day on either end? A full day? Or just a few hours?
  • What time of year will you be traveling? Are you okay with paying a premium on flights and hotels if you’re traveling during a busy season? Or would you prefer going at off-peak times/shoulder seasons for better rates? A simple search for “best time of the year to go to ___” will usually bring up articles that break down seasons at popular destinations.
  • How much do you have budgeted for the trip? How much are you comfortable spending per night on a hotel, and per day on food, activities, transportation, etc.? Be sure to check out our post on how to budget for a trip here.

Keep key travel information easily accessible

Once you have your destination decided and you’ve moved on to booking your flights and hotels, you’re going to want to keep all of that information in one easy-to-access place. This way, you’re not frantically searching for your confirmation numbers and flight times the night before your trip. 

As soon as I book my flights and hotels, I immediately add the flight numbers, flight times, and confirmation numbers to my calendar, and then send the calendar invite to anyone I’m traveling with. 

I do the same with hotel confirmations and car rentals. Depending on what calendar you use, you can also add your confirmation email as an attachment to the calendar invite.

Additionally, I create a digital folder for all confirmations & emails related to the trip. Of course, you can also do this with physical print-outs if you prefer!

Build out your itinerary 

Now to the most crucial part of your trip-planning process: building your itinerary. Typically I recommend starting out with a blank document and creating an initial outline of the trip by inputting all of the information you already know, like date of arrival and departure, confirmation numbers, hotel locations/addresses, check-in and check-out time, and any other info you have confirmed (e.g. transport to and from airport, car rental location etc.).

Once you have the bones of your itinerary built, you’ll want to build it out with details on meals and activities. If you’re like me and tend to do a lot of research prior to your trip, I’d recommend keeping a list at the bottom of your document that includes bullet points of all the top recommendations you receive. You can then choose which of those are your top priorities, and slot them into your itinerary accordingly.

Make a checklist prior to your trip

Maybe this sounds obvious, but it’s still worth pointing out. In fact, if you make the list once, you can refer back to it and use it prior to every trip. Some items to add include:

  • Check your toiletry bags to see if there’s anything that needs to be replaced
  • Buy anything specific you need for the destination (hats, hiking boots, spf, waterproof camera bag, insect repellent, etc.)
  • Double check your seat assignment for the flight and adjust if needed
  • Confirm your passport isn’t near its expiration date
  • Take out the trash and empty the refrigerator

Pack according to your itinerary 

The best thing you can do to avoid overpacking is to make sure that every item you pack is done with intention. Print out a copy of your itinerary, and jot down notes next to each day and activity with exactly what you plan to wear: top, bottom, shoes, accessories. Then once you pack those items, resist the urge to throw in extraneous things beyond what you know that you’ll need. I also find that packing cubes help a great deal in keeping myself organized, particularly on longer trips.

Hopefully you found some of these tips helpful! And remember that no matter how much you plan, hiccups are bound to happen — but sometimes, that’s when the best memories are made. Embrace the imperfections of your journey. Safe travels!