Building out your travel itinerary is where your vision comes alive! This trip itinerary planning guide will take you from DREAMING about your trip to BOOKING the most important pieces. Use the itinerary planning PDF to track it all in one place.
Trip itinerary planning should start with the experience you want. How do you know what to plan if you don’t know what you want? Once you have the experience in mind, find the activities and accommodations that bring the experience to life. And finally, book the logistics.
In case you missed it, here’s Trip Planning Step 1: Start by defining your perfect experience.
Step 1 hones in on what will make your trip FANTASTIC. This becomes the compass that guides all trip planning decisions.
Step 2 builds out that vision …
- Research ACTIVITIES: Build your itinerary must-dos
- MAP it out: A simple trip itinerary
- Pick a PLACE to stay (or two or three)
- BOOK the critical pieces
- Keep dreaming: Your itinerary maybe-dos
At the end is a list of my favorite resources that I use in this step.
Note: Some travel bloggers recommend booking your flights before looking into activities or accommodations; I disagree. Some incredible experiences book up well in advance and are only available certain days, weeks or months. Unless there’s no flexibility to when you go, first finalize your must-dos. Then plan everything else around them.
Get your FREE trip itinerary planning PDF when you subscribe to our email list. A 6-page fillable PDF that walks you through trip planning steps 1-3.
1. Research ACTIVITIES: Build Your Itinerary Must-Dos
Your first step in the trip itinerary planning process is ALL about feeding your travel fantasies. What do you KNOW you want to see and do? What are those gems you don’t know about?!
My favorite way to do this is with a Lonely Planet guidebook and highlighter in hand, sitting in a coffee shop with my favorite drink. Find your happy place and have fun!
Research your destination for must-do activities
Researching your destination is a bit of a chicken-and-egg thing. You need to know a bit about a destination before you’ll want to research it, and you need to research it to know if you actually want to go.
So, find a research process you enjoy. Books about far-off places, maps and delicious coffee all make me happy. Surround yourself with happy … it does wonders for the dreaming process!
Are you quick to go online in your research? Many people are. I get that it can be super efficient, especially if you use helpful tools like Pinterest to save and organize what you find. My Pinterest boards have some truly inspiring destinations!
BUT … may I suggest that this is also the best way to get overwhelmed? When you’re in the dreaming phase, it’s easy to get distracted and bogged down in too much detail.
How to research your destination without getting overwhelmed
This is my process for researching a travel destination. It maximizes the dreaming and minimizes the distractions that can make it overwhelming.
- Buy a paperback guidebook. Go old-school, and buy a physical guidebook for your destination. Lonely Planet guidebooks are my favorite, because they’re written by locals or frequenters to the area and feature lesser-known gems.
- Pick up a highlighter. Yup, get a highlighter in your favorite happy color. Use it sparingly to mark only the activities and accommodations you’re seriously considering; overuse can also make your guidebook overwhelming. Not good.
- Find the right time and place. Trying to plan your dream vacation while someone’s yelling at you for your attention or you’re stressed about getting dinner in the oven won’t cut it. For me, reading on public transit actually worked as long as I got a seat. But stealing time alone at a coffee shop or in the evenings with some wine was really productive.
There are two other things I love about having a paperback guidebook. First, your favorites (i.e. highlights) are automatically sorted and easy to find (as per the guidebook chapters). And second, you also have a handy reference guide while on the trip (with addresses, phone numbers, etc).
Shop Lonely Planet guidebooks on Amazon now!
Verify your must-do activities
Now that you researched your destination (with a healthy dose of dreaming), it’s time to turn on that computer. You want to verify that what you read about is still great. And to start prioritizing your must-dos versus your maybe-dos for your trip itinerary planning PDF.
How to verify must-do travel activities:
- Read traveler reviews. Start going through your highlighted activities in the guidebook and reading what travelers say about them, to see if they still sound good to you. My favorite places to read reviews is Google and Trip Advisor. Some bloggers don’t like Trip Advisor because apparently the demographic is a bit older and grumpier – this makes me chuckle, because I don’t think I fit either descriptor and I’ve been using Trip Advisor for many years! But, always with reviews, take them with a grain of salt and consider if traveler complaints would be an issue for you.
- Start a list. If activities still sound great to you and as you find others online, start adding them to a list. Some people use a spreadsheet; others use a text document; I actually just use my email. Use whatever method you like, but make it something you can access and modify wherever you might feel inspired (home, work, commuting, etc).
- Share your list. If others are going with you or you want advice from someone who’s been where you’re going, share your top to-dos with them. This is why I just build my initial list in my email. Traveler reviews are great, but reviews from people who know you are even better. This is also a great time to talk priorities with your travel companions and start navigating how you might negotiate or separate to do different priorities.
Add in details to your list of must-do activities
At this point, you’ve narrowed down the top things you and your travel companions want to see and do. Go back to your original list and strip out the things you’ve cut out. Then add to your must-do activities the details listed below.
Add the following details about your must-do activities:
- Address and general area (i.e. which city or quadrant of the city), plus any tips you read about finding it
- Website and phone number
- When it’s open or running, including days and times
- Specifics you’re interested in, like tour name or seat section
You should now have a tidy little list with your top things to see and do, along with their details. Now you can start mapping them out.
Remember to SHARE this trip planning process with your TRAVEL COMPANIONS!
2. Map it out: A simple trip itinerary
After you’ve researched and ranked the things you want to see and do, map it out – on both an actual map and a calendar. The map will give you a visual on how near or far apart everything is. And the calendar will help you plan around activities only available on certain days or times.
Together, your map and calendar will help you figure out when to group certain activities, where you might want to stay, which airport to fly into, and how you might want to get around.
Create a visual MAP for your trip
If you haven’t discovered Google My Maps, this is a great time to try it out!
A very helpful step in the trip itinerary planning process is to map out all of the activities you’re considering. Google Maps quickly shows you how near or far apart certain activities are. And it comes in super handy for figuring out the best road trip routes and public transit commutes.
Note: You won’t want to rely on Google Maps when you’re actually on your trip. Google Maps doesn’t work without internet, and it’ll quickly eat away at your data. But, there are ways to address it. To come in Step 3.
How to create a Google My Maps with your must-do activities:
Once you have a Google account, it’s easy to create and find your maps from your Google Drive.
- Search “Google My Maps” or from your Google Drive, click “New” and “More.” Click on “Create New Map.”
- Name your map and add a description.
- Use “layers” to organize your trip. For example, you might organize activities by location, activity type or must-do versus maybe-do. You can drag and drop across layers and hide layers, so you have lots of flexibility (but note that you get a maximum of 11 layers).
- Add activities within layers. Generally it’s best to use the search bar to find activities, because Google will automatically add the address and website link for you. You can also include directions between your hotel and activities (by car, transit and foot). NOTE: Directions cannot be in the same layer as locations.
- Click on “Share” to share it with others. You can share it publicly by search or link, or only with specific people. You can allow others to edit it or only view.
Create a simple CALENDAR itinerary for your trip
Even if you hate travel planning and want to do as little of it as possible, you really should do this. Plot out your must-do activities on a simple calendar so you know which days and times you’re committed. Everything else is bonus.
Many activities only happen on certain days and at certain times. Make note of any specifics for activities you really want to see and do. Then, work around them to fill in the remaining days. (Or, leave them blank to figure out when you get there.)
How to create a simple calendar itinerary with must-do activities:
Use whatever system you prefer to start plotting out when you want to do what. You might use an online calendar like Google. A spreadsheet. Or a pretty journal – just use erasable pens! The trip itinerary planning PDF has a spot to record this, too.
Here’s how to create a simple calendar trip itinerary:
- Mark in your travel start and end dates.
- Separate your days into morning, afternoon and evening.
- Transfer the things you really want to see and do into the days/times they’re available.
- Look at your map to see if there’s a natural fit to group activities in the same area on the same day or back-to-back. Do your activities follow a natural route?
- Tidy it up. I like to bold my must-dos and italicize nice-to-dos. You could color-code by companion must-dos or by activity type. Whatever makes sense for you and however planner-crazy you like to get.
The main point here is to record which days you’re committed and why. Plus your brainstorming of when it might make sense to do other things.
My top 3 tips for trip itinerary planning:
1. Take a off at home before and after your trip.
I know we’re all eager to maximize our time off work by being away as much as possible. But since I started adding a free day at home before and after, I’ve enjoyed my trip experiences SO much more. This gives you a day to finalize last-minute things before your trip and before going back to work.
BUT the main reason is that it gives you a day to mentally switch gears. It’s like taking a nice deep breath, so you can enjoy your vacation from moment #1. And let it linger when you get back. Seriously. Try it and see what you think.
2. Save your first and last days at your main destination.
This tip is similar to the first. If you’re planning a day trip away from your main destination, give yourself at least one full day at your main destination. This lets you settle in and get comfortable with getting around.
And, give yourself at least one full day back at your main destination after your day trip. Flexibility is GREAT on your last day.
3. Plan one or two things per day, plus options.
I’ve planned both go-go trips and go-with-the-flow trips. I recommend neither!
Take a good, long look at the experience you defined in Step 1. Keep this in mind when planning your itinerary.
Even if you like to pack in a ton of things to see and do, allow time for those fantastic spontaneous travel moments. To linger over a fantastic dinner with a view. Or to join new friends at a once-in-a-lifetime experience you just couldn’t plan for. And for unexpected delays.
If you like to just go with the flow, I also recommend penciling in something for every day. I HATED sitting around on my phone, researching what to do that day. What a waste of time!
A good rule of thumb is to plan one or two main activities per day. Plus a few backup ideas to choose from when weather’s bad, you feel jet-lagged, etc.
Tip: Use the trip itinerary planning PDF to capture your activity ideas.
3. Pick a place to stay (or two or three): Let the experience guide you
Now is the time to look into potential accommodations. You know when you want to do certain things and where they are. And, depending on the type of trip (i.e. road trip versus one city), you know if you’re looking at one or multiple places to stay.
I was surprised to read that SO many travelers hate picking a place to stay! Are you one of them? If yes, take a few seconds (yes, right now, please!) to write down the experience you defined when you started planning for a trip. What will make you say, “THAT was a fabulous trip”? Now look at it often while you search. Even if you’re on a budget, you CAN find your diamond in the rough!
Picking a place to stay is actually one of my favorite parts to planning a trip. It’s like being on a treasure hunt. You’re looking for that special place you want to go back to after a great day of sight-seeing. A place that aligns with what you love about your destination.
Use the trip itinerary planning PDF to compare accommodation options.
Where to search for a great place to stay on your trip:
- Google search hotels at your destination. Enter travel dates, filter by guest rating (I use 3.5+), and sort by price. You can also filter by hotel class and amenities. Google gives you a map with your results (very helpful, now that you know where most of your activities are). Plus, guest reviews from multiple platforms (like Trip Advisor and Booking.com) and prices from multiple platforms (like Booking.com and Expedia.com).
- Search “the best” and “the coolest” places to stay at your destination. Sometimes you can find a really fun place that’s a destination in its own right, but doesn’t come up on the main travel websites. Some gems just don’t list with Booking.com or Expedia.
- Check out hostelworld.com and glamping.com. These are often among the “coolest” and most fun spots that can take your trip up a few notches.
How to use traveler reviews for picking a place to stay:
- Look for patterns. If a lot of reviews tell you the rooms are dated, they’re likely dated. If some love the food and others hate it, it’s likely a matter of preference. Customer service is the biggy that’s tougher to interpret. Does a complaint read like a personality conflict with one staff member, or like a bigger issue? How did the hotel respond? Was it an issue you’d worry about?
- Beware the complainer syndrome. Take one-off comments with a grain of salt. Some people are impossible to please, especially if they’re used to a different style of accommodation than what they’re reviewing. Or they’re generally unhappy with their vacation. Again, consider if it’s about something you’d worry about.
- Follow your no-go hunch. Certain comments flag enough for me that I won’t book a place. Like patterns of poor cleaning service or bedbugs. Or security issues handled badly. Let your spidey senses guide you.
SHARE your top picks for places to stay
Now, add your top potential places to stay to your map. Do a few rise to the surface? Are some in great central locations or along public transit, so it’d be easy to get around? Do some offer great value beyond price and location, so you’d actually enjoy staying there? Do they align with the experience you’re looking for?
Hopefully you naturally narrowed down your search to 3 favorites. Yes or no, it’s time to tap into your travel companions.
Add your favorite places to stay to your list of activities (so everything is together in one place). The trip itinerary planning PDF has space to record and compare your top accommodations, too.
Details to include on your list of potential hotels:
- Address and general area (i.e. which city or quadrant of the city), plus any tips you read about finding it
- Website and phone number
- Cost, plus any extra fees like resort fee, parking, breakfast, etc
- Features you like, plus how close it is to public transit and activities
- Initial thoughts on what you like and what you’re hesitant about, including traveler reviews
Send your list, map and calendar to your travel companions to get their thoughts. Again, your trip itinerary planning PDF is an easy way to this.
Want more tips? Check out: 21 Tips to Pick BETTER Accommodations for your Trip
You’re SO close to getting this wrapped up!! Hang in there!
4. Book the critical pieces
Whew … you’ve done a TON of work. You know the experience you want, and you know what’ll get you there. Now it’s time to book the time off work and lay down some cash.
WHEN to book your trip
When you should start booking your trip will depend on where you’re going, when, and if you need a travel visa.
- If you need a travel visa, apply for it as soon as you know your dates.
- If you’re going to a popular place like Maui over the busy Christmas season, plan to book it about a year away so you get the hotel you want.
- All other destinations are usually fine booking two months out.
As soon as I know my dates, I’ll start monitoring flight deals. I really like Expedia.com for this because they pull from various companies.
WHAT to book soon
The key things I book sooner rather than later, and in this order, are:
- Insurance (if you’re getting it)
- Key activities you’d be really sad to miss out on
- Accommodation (your initial one, at least)
Record your booking confirmation details on the trip itinerary planning PDF.
Look into travel insurance
The specific travel insurance that makes sense for you will depend on many different factors about you and your trip. I generally don’t get trip cancellation or interruption insurance unless I’m spending a lot in advance. But I’ll always get emergency medical coverage and full car rental coverage.
Before deciding on what type of travel insurance to get, look into what you already have (and clarify anything you don’t understand):
- Credit cards often insure trip cancellation and interruption up to certain amounts as well as certain aspects of car rental insurance.
- Private health insurance benefits (i.e. through your employer) sometimes include some coverage for emergency medical services while traveling. Make sure you read any exclusions in detail.
- Personal car insurance will sometimes include coverage on car rentals.
Keep in mind that third-party travel insurance is usually best. This is because you get to decide how to spend the money.
Remember: You can’t get travel insurance after something goes wrong. Buy it as soon as possible after your first major purchase (like flights or a cruise).
A helpful post on buying travel insurance is by fellow travel blogger NomadicMatt.com.
5. Keep dreaming: Your itinerary maybe-do activities
Now that your main trip itinerary planning is done, take a loooong deep breath. When it’s fun again, go back to your activities list, map and calendar to consider how you might want to fill in the blanks.
Some people love leaving a lot up in the air until they’re at their destination; if that’s you, awesome! Just keep in mind that this might drive your travel companions crazy!
I’ve come to appreciate the art of slowing things down and living in the moment while on vacation. But, I hate feeling like I’m wasting my time on vacation pouring over internet reviews to decide on the best tour to take. I’d much rather have done my research ahead of time so it’s a quick reservation and then off to enjoy my day.
So, add your “maybe” activities to your list of things to see and do. Include their details so it’s easy to book whenever you decide. And pencil them into the calendar on your trip itinerary planning PDF for a day and time you think they’d fit.
This is a win-win approach for planner lovers and planner haters!
Get your FREE Trip Itinerary Planning PDF when you subscribe to our email list! A 6-page fillable PDF that walks you through trip planning steps 1-3.
Summary and Resources
Planning your trip doesn’t have to suck! Find your happy place, plant yourself in it, and let the experience you want guide you. That’s why I highly recommend plenty of time with your favorite coffee.
Step 2 has taken you from dreaming and researching about your trip to booking its critical pieces. The trip itinerary planning PDF captures the details of your activities, hotels and bookings. Now you can linger over all the other activities you’re debating between. (And compare/contrast them to death?? Anyone else out there like me?)
Remember: The KEY to getting the trip you want is keeping the experience you want at the very center of all your trip planning research and decision-making. It’s your guiding light – your compass to getting YOUR perfect experience.
If you missed it, be sure to read Trip Planning Step 1: Define your perfect experience.
Favorite resources for trip itinerary planning:
- Destination research: Lonely Planet guidebooks.
- Verify research: TripAdvisor.com for traveler reviews on things to see and do; Google and Booking.com for traveler reviews on hotels
- Accommodations: Also check out hostelworld.com and glamping.com for fun and surprising options
- Booking critical pieces: Expedia.com for flights; Booking.com for hotels; and TripAdvisor.com for activities
- A travel journal! If journaling and doodling make you happy, make it part of your trip planning process. My favorite spot with everything you need to start your own bullet travel journal is on DIYCraftClub.com.