Do you ever feel overwhelmed by everything that needs to get done when organizing your trips? As exciting as travel can be, for some people the planning phase of the process is the worst part. It can get stressful keeping track of booking information, and reservations, researching a destination, and actually preparing for the trip itself.
For me, planning is one of my favorite parts of travel! I love getting excited as I research a destination, I love finding a good deal on a flight or discovering an adorable hotel with a fantastic view. I get excited watching the trip come together and creating the checklists of everything I need to feel fully prepared for the adventure.
After organizing almost 30 trips for clients, friends, and family, I’ve started to compile resources and strategies that have made the process easier. So let’s break it down!
I’ll share specific apps or tools to help organize your trip for each stage of the travel planning process. Throughout this post, you’ll find personal tips from my own travel planning experience that I hope will help make organizing trips easier for you!
*Disclosure: This article contains affiliate links. If you make a purchase after clicking one of these links, I earn a small commission at no extra cost to you.
Decide your dates & destination
Funnily enough, this can sometimes be the hardest part because there are so many options out there! Think about what you want to get out of your trip. Do you want to relax? Are you interested in cities? Is there something or someplace really high on your bucket list? I go into more tips on deciding where you want to go in a different blog post. Here I want to talk about tools and tips that can make organizing your trip options easier.
For me, organizing trips starts with inspiration. I have been compiling trip inspiration on Pinterest and Instagram for YEARS. If I see a photo or video that excites me or makes me want to visit a destination, I save it. Start saving things now! But don’t just ‘save’ them; organize them.
Organizing tip:
On both Pinterest and Instagram, I create folders dedicated to trip inspiration. I create a folder per country/destination so as I go about my days I can add to these folders at any time.
They are great to refer back to at a later date when I am looking for ideas of where to go. I’ll take a look at what I’ve saved in the past and compare it to my travel current travel goals. This has saved me SO much time. It may seem so logical and simple, but creating destination folders, not just ‘Europe destinations’ or ‘Travel Inspo’, was a game changer for me.
Create an itinerary outline
Once you have your dates and destination chosen, it’s time to actually start travel planning. First things first, start with an outline. Don’t go into the planning too quickly by planning your trip day by day just yet. Start broad and work your way to finalizing details.
The first step in building your itinerary outline; list out your days. Then decide where you want to go. For instance, if you are planning a trip to France, are you interested in Paris? The French Riviera? Both? At this stage, I’d advise doing a quick research on how many days are needed per location. This will help you build your outline.
Organizing tip:
I use Thatch to build my itineraries and outlines. It has a map feature so I can see all of the destinations featured in my itinerary and I can keep track of all of my notes in one place. Its also super mobile friendly which is great when I’m actually on my trip and need to refer back to any trip details.
Remember, at this point, things shouldn’t be too detailed. All you’ll need in your itinerary for now is the day you arrive, the number of days you want to spend in each place, and when you leave. You want things to remain relatively flexible as you move onto the booking stage of organizing your trips.
Did you know? I offer custom travel guides and travel planning services. I have helped clients choose their next destination, given personalized recommendations and helped organize their itinerary. Find out more about my services on my Thatch page!
Start making bookings
This is a big step. And probably one of the most overwhelming. People are often concerned about getting the right deal, missing out on availability, and keeping track of all of their bookings.
Here are some quick tips on knowing when to start booking your trip:
✈️ Flights: 3-10 months in advance
🚗 Car rental: 3 months in advance
🚂 Trains: 2-4 months in advance
🏨 Accommodations: although the closer to your date the cheaper the prices will be, it also means options will be slim – I always opt for the sooner the better
PRO TIP: If you are traveling with multiple people and you are dividing the bookings, use Splittr to keep track of what everyone owes each other. This app has been a GAME CHANGER! You input what you spent, and who participated in the expense and it tracks everything for you. It will calculate what everyone owes so you don’t have to worry about it! Create a Splittr at the beginning of your trip and settle up at the very end, its super simple to use!
Organizing tip:
As you book, add the details to your trip itinerary immediately after it’s confirmed. Every date, time, flight number, and booking confirmation should go directly into the itinerary. This is the easiest way to keep track of everything and you’ll be happy you wrote it down in one place. You don’t want to have to go digging through many confirmation emails just to find something quick.
I first book international flights, then local travel (trains, buses, flights, car rentals etc.) then accommodations.
Here are some tools I use when organizing trips:
✈️ Flights: I use Skyscanner to find the cheapest and/or the most direct flight to my destination. I’d also advise looking at Skyscanner when you are deciding your travel dates. Sometimes leaving a day earlier/later can save you some money. Check first to make sure you find the right deal! This applies not just to international flights but to domestic flights as well. For Europe, I usually domestically fly with Volotea, Easyjet, or RyanAir. Using Skyscanner I’ll find the best day and/or time to fly and update my itinerary accordingly.
🚗 Car rental: For my most recent trips I have been using rentalcars.com because rather than researching each company individually (which is what I used to do), it compares everything all on one platform. Remember, add your reservation information to your itinerary!
🚂 Trains: I have been using Trainline for over 4 years. Similar to rentalcars.com this site compares the different routes and providers so you can find the best route and deal for you. Omio is another reliable site that I’ve used in the UK and the Balkans!
🏨 Accommodations: I have recently been using Google Travel. They’ll list all of the hotels and hostels from providers like Booking.com, Hostelworld, and Expedia all in one place. What to look for? Look at location, price, and reviews at least. I usually end up booking with Booking.com, Tripadvisor or Airbnb.
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Reserve activities & restaurants
You itinerary should now include more details than when you first started with the outline. You’ll now have accurate dates and times to work with along with your booking information. Now you can look at the amount of time you have and can begin researching what you want to do.
Now, as much as I am a planner, sometimes you’ll want to make sure you just wander and explore a destination. But, you also do not want to miss out on seeing or trying something because you didn’t take the time to look at it beforehand.
This is an excellent moment to look back at your saved folders. What experiences are most important to you? Are they popular attractions? Do you need to look for tours or will you explore on your own? Deciding on how to spend your time, whether its pre-planned or not, is a personal preference. But you can look for ideas on Viator, Tripadvisor, and GetYourGuide for tours, tickets, and experiences. Here are some of the coolest ones I’ve done recently:
🏄🏼♀️ Surf Lessons in Portugal
🍫 Chocolate making class in Belgium
Organizing tip:
Before Covid-19, walk-ins were very common. Spontaneously showing up to a restaurant or deciding in the moment you want go pop into this museum was the norm. Now you can still do this, but take it from my own experience, walk-ins are becoming less common, especially in peak season.
For example, on my last visit to Paris, I wanted to go to the Saint Chapelle. When I went to book tickets the night before, everything was sold out for the week. This is not necessarily true for all destinations but for places and restaurants you KNOW with certainty you want to go to, book it in advance just to be safe.
Prepare for your trip
At this point, your itinerary is pretty much complete! You have your travel information included, your accommodations mapped out and any important tour or activities reserved! But organizing your trips doesn’t stop here. Now it’s time to prepare for your trip.
At this stage, I usually create a checklist. This is the easiest way to organize what needs to get done leading up to the trip.
Here are the important steps to the final stage of preparing your trip:
Choosing Travel Insurance
I’ve been finding ways to reduce my stress when organizing trips and using travel insurance has been a great stress relief for me. Especially in new countries where I am out of my comfort zone, having that extra protection puts me at ease.
On my most recent trip to Morocco, it was our first trip to Africa. We had heard of people having stomach issues and we had some exciting activities planned so we were a little anxious imagining the ‘worst case scenarios’. I knew that in order to be fully present in the experience of discovering Morocco, I needed the worries of something going wrong off my mind.
SafetyWing has been a great option for travelers, remote workers, and digital nomads because they are affordable and flexible! Plus, their Nomad Insurance now has a 0$ deductible! Similar to a subscription, you can start your policy at any moment during your trip and extend it as often as you’d like. It’s definitely a travel essential we’ve started adding to our trip preparation checklist!
Read more on their official site here!
Checking your travel documents
Do you need a visa to visit the country? What are the requirements? How much does it cost? How do you apply for it? These are the types of questions to keep in mind when looking into tourist visas! Add any essential steps to your trip preparation checklist!
You also should check your passport expiry date. My family has had horrible stories of people being stranded. They were not allowed to enter a destination because their passports were close to expiring. Check the regulations first.
You might also need vaccines and proof of vaccinations in certain countries. You can find out what vaccines you might need doing a quick google search or by speaking with your family doctor directly.
PRO TIP: Make sure to have copies of all of your important travel documents!
Packing
There are 2 steps to my packing process. 1) Check my packing list. I have a packing list I refer to that is as thorough as I can make it. Part of this also means researching what the weather will be like in my destination of choice. 2) Use packing cubes. Packing cubes has been a great way to save space and stay organized. You can have designated packing cubes for a type of clothing making it easier to find in your suitcase. There are lots of ways to save space but this one has been the most effective for me!
READ MORE: Travel Planning 101: How to plan your next adventure
Feeling more organized yet?
I hope by now you have found at least one tool, resource, or tip that you can take with you when organizing your trips. These are just some of the ways I keep on top of my planning and itinerary that has made the process less overwhelming.
If you need more happy with your travel planning, I also offer consultation calls and custom planning services. Whether you are looking for a custom list of recommendations or someone to make your itinerary for you, I’d love to help! I specialize in France and the UK as I have lived in both countries and explored them both in great detail! I hope I can help take off some of the travel planning stress off your plate!
