Browsing travel guides and maps over delicious coffee

Trip Planning Step 2: Build Your Itinerary and Book

Building out your trip is where your dream comes alive! This post will take you from DREAMING about your trip to BOOKING the most important pieces. Even if you hate planning trips, give this post a try: simply follow along with a scrap piece of paper. Your style; your dream; your trip.

One of the main reasons why so many people hate trip planning is because they skipped the first step: defining the experience you want. Most travel blogs I read completely ignore this step, but it’s the MOST important piece to getting the trip you want – AND to making the planning process fun. Yes, fun!

In case you missed it, here’s Trip Planning Step 1: Define YOUR perfect experience.

Step 1 covered your default travel style, what you know about your trip, your constraints, and goal. This goal becomes your COMPASS to help you make the best decisions for your trip.

Now we’ll start building the dream …

CONTENTS

  1. Read, highlight and rank: Your itinerary must-dos 
  2. Map it out: Google Maps and a simple calendar itinerary 
  3. Pick a place to stay (or two or three) 
  4. Book the critical pieces 
  5. 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 truly no flexibility to when you go, give yourself the chance to finalize your must-dos first, and then plan everything else around them.

Remember to SHARE this trip planning process with your TRAVEL COMPANIONS!

1. Read, Highlight and Rank: Your Itinerary Must-Dos

Trip planning 3-step process: infographic

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This step is about feeding your travel fantasies! 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!

We’ve already established that many of you hate planning your trips. One big reason is not defining the experience you want (i.e. Step 1 of this trip planning process); another is that you don’t let yourself dream enough. (If you’re like my husband, you’re rolling your eyes right about now. I get it, it’s cheesy. BUT, I love planning my trips, so maybe I have a few things figured out?? Stay with me … !)

Research your destination for must-dos

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 embracing the fun and happy of travel planning, and avoiding the distractions and detail 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: your favorites (i.e. highlights) are automatically sorted and easy to find (as per the guidebook chapters); and, 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-dos

Now that you researched your destination (with a healthy dose of dreaming), it’s time to turn on that computer.

Here’s how to transition from researching your destination to building your priority list of must-dos:

  • 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-dos

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.

Add the following details about your must-dos to your list:

  • 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

At the end of Read, Highlight and Rank, you should have a tidy little list with your top things to see and do, along with their details. Now you can start mapping them out.

2. Map it out: Google Maps and a simple calendar itinerary for your trip

Woman writing in a journal mark up a journal over a warm cup of coffee

Photo credit: Green Chameleon from Unsplash.

After you’ve researched and ranked the things you want to see and do, map it out – both on 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 you might want 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 planning process is to map out a visual with all of the activities you’re considering on Google My Maps. Google Maps comes in super handy for figuring out your road trip routes and public transit commutes.

Note: You won’t want to rely on Google Maps when you’re actually on your trip. We’ll get into this in Step 3, but in short, 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-dos:

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 that directions must be in a separate layer, so I find it simplest to have them all in one.
  • 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 you’re committed. Everything else is gravy.

Many activities only happen on certain days and many activities don’t happen on certain days; 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 your must-dos (online or paper):

Use whatever system you prefer to start plotting out when you want to do what: an online calendar like Google; a spreadsheet; or a pretty journal – just use erasable pens! Here’s how to create a simple trip calendar:

  • 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 grouping 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 creating your trip itinerary:

  1. Bookend your trip with a day off before and after. I know we’re all eager to maximize our time off work by being on the trip, but since I started adding a free day 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 start enjoying your vacation from moment #1 and let it linger when you get back. Seriously. Try it and see what you think.
  2. Bookend day trips to other cities with full 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 so you can settle in and get comfortable with getting around. And, give yourself at least one full day back at your main destination after, so you have flexibility to wrap up your trip with anything you weren’t able to see or do yet (like trinket-shopping for those back home).
  3. Plan one or two things per day, plus options. I’ve planned go-go-go trips and learned that it’s better not to do this. Take a good, long look at the experience you defined in Step 1; now, 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 to linger over a fantastic dinner with a view or join new friends at a once-in-a-lifetime experience you just couldn’t plan for. Or for unexpected delays. A good rule of thumb is to plan one or two main activities per day, with a few ideas you can pick and choose from when you know the weather, how you feel, etc.

3. Pick a place to stay (or two or three): Let the experience guide you

Swaying in a tree swing surrounded by jungle and water

Use the EXPERIENCE to guide where you stay! Photo credit: Taylor Simpson from Unsplash.

Now is the time to look into potential accommodation. 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 have a sense of whether you’re looking at one or multiple places to stay.

I was surprised to read that so many travelers also 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 in Step 1; 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 of the trip planning process. 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.

Where to search for a great place to stay on your trip:

  • Google search hotels at your destination. You can 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!), a compilation of reviews from guests across 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.
  • 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 (in which case, you can just eat somewhere else). Customer service is the biggy that’s tougher to interpret; does it read like a personality conflict with one staff member? 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 are 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 planning 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 from that destination?

Hopefully you naturally narrowed down your search to 3 favorites. Yes or no, it’s time to tap into your travel companions.

Add your top potential places to stay to your list of activities (so everything is together in one place).

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.

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:

  • Flights
  • Insurance (if you’re getting it)
  • Key activities you’d be really sad to miss out on
  • Accommodation (your initial one, at least)

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 make sure I have 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; so, 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-dos

Single boat floating under beautiful skies in Ha Long Bay, Vietnam

Floating along in the beautiful Ha Long Bay, Vietnam

Now that you have the main pieces of your trip figured out and secured, take a loooong deep breath. And when it’s fun again, go back to your 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 maybes to your list of things to see and do. Add their details so they’re easy to book whenever you’ve decided, and pencil them into your calendar for a day and time you think would be easy and fun to fit them in.

And it’s a win-win for planner lovers and planner haters!

Summary and Resources

Planning your trip doesn’t have to suck! Find your happy place, plant yourself firmly in it, and let your dream 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. 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.

My favorite resources for building out my itinerary and booking my trip are:

The FINAL STEP in the trip planning process is where we pull in all the loose strings and tie them up into a pretty little bow. Continue on to Trip Planning Step 3: Count Down with Your Ultimate Checklist

Trip planning 3-step process: infographic

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