Travel Itinerary Planner: How We Plan For Trips

Computer planning

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Travel Itinerary Planner: How We Plan For Trips

Recently someone reached out to us asking how we typically plan our trips including details like determining what places and cities to visit, how we find and select our accommodations, how do we decide where to dine, and more. It blew my mind because although we write and talk about travel ALL. THE. TIME. we don’t have a specific blog post dedicated to the process of planning a trip. So I figured it’s time that changed. 

In this post, we’ll be explaining our trip planning process in detail. Our process may be different than yours, and that’s totally fine! In fact, we’ve now been curious about how others plan their trips in case we’re missing something big. But here is the gist of how we create a travel itinerary planner for each of our trips!

Selecting What Destination To Visit

There are a number of ways that we select what destination to visit, especially with international travel. We’ll go through each of them here.

  1. Look for cheap flights to places you’re interested in going to. The first thing to know about this is that you might have to be flexible! Let’s say we want to visit somewhere in Europe. We first go to Google Flights and set up price tracking from our airport or nearby airports to the destinations we’re interested in. Then we get emails every time the price on the flight changes! When we find a cheap flight deal, we go with it or continue to track.
  2. Save for places that we REALLY want to visit. Before we left for Japan for three months we spent THREE YEARS saving money and accumulating credit card points for the trip. Now obviously not everyone is going to hop on a plane and live in another country for three months, we get that, and honestly, that’s not our normal. But, if you have a dream to visit Greece; start tracking flight prices, saving money, and consider opening up a credit card to get points to use on your trip.
  3. For U.S.-based travel we look at a number of factors including cities and states we’d like to visit, whether we can fly or drive, and attractions we’d like to see. Once we’ve determined our mode of transportation we start planning our route and booking reservations (more on this in a moment!).

Finding Cheap Flights

If you enjoy traveling you probably already know that there are a good number of airline websites to compare prices. Our personal favorites are Kayak, Skyscanner, and Google Flights. Like I said above, we set up price tracking on Google Flights for destinations we’re interested in (even in the United States!). Then we receive an email if that price drops or goes up! Kayak also has a price tracking feature. 

If you are flexible with where you want to travel and when Skyscanner has an “everywhere” option where you can pick specific dates or a range of dates and see where you can get the most bang for your buck.

Another tool we use to find cheap flights is Scott’s Cheap Flights. It’s an email newsletter that offers a free version and a paid one which allows you to see more flight deals. We can’t attest to the paid version of Scott’s Cheap Flights but definitely sign-up for the free version to start! This is how we find a number of “error fare” flights.

What is an error fare or mistake fare flight? To put it simply, an error fare flight is when an online travel agency sells an airline ticket for MUCH less than they planned to by mistake. If you’re interested in knowing more about how this works this article explains in detail. But when an error fare pops up, it usually lasts less than 24 hours before the mistake is found. 

We’ve seen this happen a few times, most recently when booking our trip to Spain and Portugal which we got for $650 RT from our small airport in Northwest Arkansas! Normally a flight like this would have been anywhere from $1,000-$1,500 RT.

Our Favorite Travel Resources for Finding Cheap Flights

  • Google Flights: Finds and tracks prices for flight deals.
  • Skyscanner: Finds and compares prices for flight deals with most major airlines.
  • Kayak: Finds and compares prices for flight deals with most major airlines. They also track prices.
  • Cleverlayover: If you are okay with having a long layover in another travel destination, say a 20-hour layover in Singapore, anyone? Then you might consider booking on Cleverlayover to save money and enjoy an additional city while traveling.
  • Scott’s Cheap Flights: Sends out error fare and cheap flight deals straight to your inbox!

Figuring Out Transportation

Large coach bus in Japan
Highway bus in Japan.

Once you’ve secured your flights it’s time to figure out the next part of this travel itinerary planner, transportation. Depending on your destination there could be a variety of transportation options so it’s best to research online to find the best mode(s).

Air Travel

You’ve probably booked flights to and from your initial destination but if you are planning to visit other locations in the place you’re visiting one transportation option is flying. For example, when we flew to Barcelona, Spain we knew we wanted to visit Lisbon, Portugal for a few days. We looked at taking a train but found that flying was going to be a cheaper and better use of our time. Hence, if visiting more than one destination, you might consider flying to each place.

Renting A Car

One of the most common modes of transportation in any travel itinerary planner is by renting a car to use for your trip. Again, depending on your travel destination, renting a car could be your best bet or be unnecessary. For example, if traveling in the United States, renting a car is usually a valid option because public transportation is limited in most areas. But if you’re traveling to New York City for a weekend, renting a car isn’t necessary.

Another example of this is if you’re trying to get to remote destinations. We’ve rented cars for road tripping around Northern Ireland and the Republic of Ireland where we wouldn’t have been able to venture nearly as far without a rental car. We’ve also rented a car for over a month in Japan to visit some of the lesser known regions of Japan or those who had less public transportation.

Utilizing Public Transportation

There are many modes of public transportation that could be helpful as ways to get around your travel destination. A few of these include trains, subways, public buses, taxis, and rideshare programs. Each of these types of public transportation is usually very efficient depending on where you’re visiting.

For instance, if you’re planning to visit Tokyo, trains, and subway systems are the most common and efficient modes of public transportation. Whereas in Kyoto trains and subways are still common, but public buses tend to be used more heavily. In San Francisco, we utilized their BART train system a few times but found rideshare like Uber or Lyft to cost less for the two of us most of the time.

Our Favorite Travel Resources for Transportation

  • Google Maps: The top dog of all travel needs, we cover this extensively so I won’t go into it too much here, but you can easily find your way from point A to point B by using Google Maps.
  • Rome2Rio: This site quickly identifies route options (air, car, bus, etc.) and allows you to easily compare costs, time, and ease of access.
  • Hyperdia: This website and app is a lifesaver for those traveling in Japan. It shows you train timetables, platforms, cost, etc so you can effectively plan your train travel (especially when booking shinkansen tickets).
  • Uber or Lyft: These are the two most commonly used rideshare apps on the market. They’re often cheaper than hiring a taxi and can be quicker too!
  • JapanTaxi: This taxi app is exclusively for Japan and while Japan has great public transportation, you might consider hiring a taxi driver if you are moving hotels or need an early ride to the airport. Rideshare programs are just starting in Japan, so taxis are still very much in use.
  • Cabify: Cabify is a rideshare app that is similar to Uber or Lyft but operates in Spain, Portugal, and Latin America.
  • Turo: Think of it as the Airbnb of cars. Rent a basic vehicle or the luxury car of your dreams for a fraction of the normal price.

Beginning Initial Research For Your Trip

After we book a flight and determine transportation options we tend to create a fresh Google Doc so we can both add things to do, restaurants, articles, and other ideas as we begin researching. Then we go straight to Google Maps and determine what cities or towns we’d like to visit.

There are always the obvious places like major cities, national parks, etc. But often we find smaller more untouched places by clicking on different places on the map. We also do searches on Pinterest and Google to find more information about our destination(s).

Search on Google

A quick Google search for the place(s) you’ll be visiting will surely bring a few ideas for items to add to your trip itinerary. We typically search for broad terms first like things to do in Madrid, Spain then once we figure out the gist of what to do in that place, we search for more specific things such as best brunch in the Malasana neighborhood in Madrid.

Searching for both general and specific terms helps you find relevant information to include in your itinerary from numerous resources, including travel blogs like ours! After finding these articles we save the links to our Google doc so we can reference them easily.

Search on Pinterest

Did you know that Pinterest is a search engine, not social media? There is A TON of valuable content on Pinterest that can help you plan a trip. After logging onto Pinterest I usually begin by searching for information about the state or country I’m visiting followed by specific cities and attractions.

I click through briefly to the website that a Pinterest graphic leads me to in order to determine if it will be a resource for my trip. If so, I save the Pin to a Pinterest board for that specific destination so I can keep track of them and/or link the article in my Google doc that I use for my itinerary in order to remind myself to look back at it.

Hey, while you’re at it, come take a look at our Pinterest page!

Click Around On Google Maps and SAVE

Logan always calls this game of mine “Google Maps roulette” because what I basically do is zoom in on a city, town, or country, and begin clicking the pins on Google Maps. When I find something interesting that we might want to visit I save the pins/destinations.

You can save them in a number of ways but this is the way that we do it. When you click “save” there are four options that pop up: favorites (pink heart icon), want to go (green flag icon), starred places (yellow star icon), or new list (which saves the item in a list for you to easily see). 

Here is how we typically do this:

  1. Favorites – Places we have visited, loved, and want to visit again.
  2. Want to go – Places we would like to visit (we change these to “favorites” or add them to a list whenever we do visit them)
  3. Starred places – Places we find on Google Maps that aren’t added already, THEN we label.
  4. New list – In addition to one of the three options above, we add all the places in one specific city (i.e. Osaka, Tokyo, Lisbon, etc) to a list so we can keep them organized.

Because I’m a visual person I’ve included examples below for those who it might help! 

Scroll and Search On Instagram

Bridge in Japan - travel itinerary planner
When searching for places to add to our Japan road trip we came across this unique road on Instagram!

Instagram has been getting a lot of heat lately because of its ever-changing algorithm, but that doesn’t mean it isn’t a reliable travel resource. We use Instagram A LOT when planning our trips by searching for geotagged locations and common hashtags. In fact, so many places we’ve found have been due to Instagram. If you find something that you like while searching you can save the image and even create a folder for specific destinations.

Here you can stalk our Instagram account. 😉

Creating A Rough Itinerary

After determining where we’d like to visit and saving places we want to visit we then start creating a rough travel itinerary on our Google Doc. Typically start this by creating a 1×14 table (or however many spots you want on the rows) so we can fill in the date at the top of the post and fill in information underneath. 

With each day having its own section helps delineate between days and avoids confusion. In this template, we include accommodation options, places to eat, and the attractions we’re interested in. We usually link to their website or booking platform so we can reference it again as we read reviews and compare prices. We’ll go into specific ways to organize your itinerary later on.

Finding and Booking the Best Accommodations

Japanese and Western style Hybrid Hotel Room at Nishimuraya Hotel Shogetsutei - Kinosaki Onsen, Japan
Room at Nishimuraya Hotel Shogetsutei in Kinosaki Onsen, Japan

When booking hotels we use a variety of different websites to read reviews about the properties, compare prices, and view photos of the rooms. When we find places we like we save a link to the property in our rough itinerary on our Google doc and title it with the name of the hotel and put the cost next to it.

After, we look at where the property is located and compare its location with the places we want to visit to see if it’s ideal (seeing how close it is to public transportation might be another step to take too!). Once we’ve narrowed it down by price, location, and reviews we book the place that suits our needs best. We typically compare the property on 2-3 websites before we decide.

Our Favorite Travel Resources for Finding The Best Accommodations

  • TripAdvisor: We typically compare TripAdvisor with the results we find in Kayak, Booking, and Expedia so these websites are used interchangeably. Looking for the best rate and reviews of the hotel we’re interested in are two criteria we highly consider when making our decision.
  • Kayak
  • Expedia
  • Airbnb: While some people have had negative experiences with Airbnb, we’ve had nothing but positive. Sure, some places might be a little outdated, but if you read reviews of the place you’re choosing to stay in, typically they ring true. We never book an Airbnb that is a new property or doesn’t have reviews. When booking in certain countries be sure to read the laws set in place for Airbnb type properties.

    For instance, in some parts of Europe, Airbnb isn’t the best choice because of the gentrification of the area. While we were in Japan, they were in the middle of changing the laws for Airbnb to where all owners had to have their property registered with the government. It’s always best to make sure to ask for their Government ID number if for some reason it isn’t listed. We’ve stayed in countless Airbnb in the United States, Ireland, Northern Ireland, and Japan without having any major issues.
  • Agoda: Agoda is another booking website that we used when searching for hotel properties in Japan. Although, it also has properties in other locations.
  • If you’re planning to book a National Park campsite you’ll need to create a account and book your accommodation through their site! It also has many helpful tips regarding the campsites at national parks.

Finding Places to Eat

Two bowls of udon noodles and two onigiri (rice balls)
Udon noodle bowls and onigiri from Karonouron.

I’ll be the first to admit that while food and local cuisine is one of the most important things to us when we travel, we have the hardest time planning it because of a number of reasons. It can be hard to narrow down dining options, fit them best into our schedule, or we might not really be feeling that specific type of food that day whereas we were before. But, one thing we’ve recently started doing is saving the restaurants we find on Google Maps and include them in our travel itinerary planner by area/neighborhood/etc. giving ourselves a few options.

Our Favorite Travel Resources for Dining Ideas

  • Google Maps: Again, Google Maps is king, zoom in on the city you’re visiting, find that little orange fork and spoon icon, and click away! This way you can see the name of the restaurant, photos of the food taken by others, reviews by previous patrons, opening hours, and the restaurant website which we suggest clicking on to see if they have a menu! Don’t forget to save it if you’re interested before clicking another pin!
  • TripAdvisor: Although TripAdvisor often has most of the touristy restaurants ranked first, we find that most of the time their touristy for a reason and we know that we can visit almost any of the top places listed and have a decent bite to eat. TripAdvisor also offers photos and helpful reviews. Another reason we like TripAdvisor is to cross-reference our findings on Google.
  • Yelp: Logan isn’t the biggest fan of Yelp because they often review and filter many of the reviews (positive and negative) placed on their site. But it can still be helpful in finding dining locations and some reviews.
  • Local Websites: If you happen to be visiting a city or area that has a local tourism website take a look at their page for restaurant ideas. Many tourism bureaus have locally owned, tried and true favorites that they list on their site for ideas!
  • Word of Mouth: Sometimes the best way to find a terrific hole-in-the-wall restaurant is by asking locals! We’ve found some of the most amazing places this way on our travels.

Finalizing Your Travel Planner Itinerary

So by now, you should have your flights booked, transportation options determined, accommodations solidified, and a list of things to do in “____” that you’re getting pretty excited about! The first thing to do with this list is to determine which activities or attractions require advanced booking and determine the hours of operation for each attraction.

The easiest way to make a seamless itinerary is by adding the information as you book it so you don’t have to dig up the information up later. Trust us, having it all in one place is way easier to manage. 🙂

Here are some things you should now include in your trip itinerary:

  • Flight Information: Including dates and times, confirmation numbers, seat assignments, airline information, cost, etc.
  • Rental Car Information: Including pick-up and drop-off times, confirmation numbers, type of vehicle, cost, etc.
  • Accommodation Information: Including dates, check-in and check-out times, confirmation number, room information, cost, etc.
  • Reservation Information: This could be reservations for attractions or restaurants. Be sure to include any confirmation numbers, dates and times, and cost (if an excursion or attraction).
  • Restaurant Ideas: A variety of choices in each area you’ll be visiting so you have options and back-up plans in case one of them doesn’t work out!
  • Daily Itinerary Ideas: Each day should have its own section with times (if there are specific reserved times) to visit attractions plus a little bit about that attraction! Trust us, it can be hard to remember what’s what when planning a trip. We like to link the attraction to its website or TripAdvisor page as well in order to remind ourselves of what we’re visiting. Include your restaurant ideas for the day as well and any other pertinent information regarding your day.

Travel Safety Information

Trip Insurance

One of the most important things you cannot afford to skip is booking trip insurance. Some credit cards, like the Chase Sapphire Reserve, offer decent trip insurance for trips less than 30 days, so the first step we recommend is to check your credit cards and see if any of them offer trip insurance. If so, make sure you book your flights, hotels, attractions, etc on that specific card.

If you do not have credit cards or a credit card that offers trip insurance you’ll definitely want to get some. Trip insurance is typically a small cost to pay for peace of mind while preparing and enjoying your trip. The trip insurance companies we recommend are World Nomads and Allianz.

Keeping Track of Travel Costs

Budgeting for travel can be one of the most difficult parts to plan for any trip. But keeping track of expenses will help you plan accordingly for unseen costs and help you manage your spending. We do this in a few ways before, during, and after our travels but follow the budgeting method that works for you best. If you’re looking for some additional ways to budget for travel, here are some ways to make money traveling.

Before Your Trip

  • Create a spreadsheet (Google Sheet or Excel Spreadsheet) to keep track of your expenses.
  • For anything paid for or booked in advance, save all emails and digital receipts in a folder on your email. For example, in our Gmail account, we have a labeled folder for ALL of our reservations, receipts, and information regarding our recent trip to Maui.
  • Set up an account with a finance app/website, like Mint to keep your finances organized when planning your trip and to check on after your trip. You can even set a specific budget to stay within for your trip.

During Your Trip

  • Save your travel receipts so you can add them to your spreadsheet and/or Mint later.

After Your Trip

  • Add expenses and a description to your trip spreadsheet from your credit card statements and receipts.
  • Label and organize your expenses on Mint.

You might also like: Traveling for Next to Nothing Using Credit Card Points and Miles

Specific Helpful Tips for Travel

Research The Culture And Customs

We believe that every person should do their due diligence and research the culture and customs of any place before they visit, this also applies to other areas of the United States too due to complicated history and regional differences. Taking time to do this step will help you from committing potentially embarrassing faux pas, but it also will help you have a deeper understanding of the place you are visiting.

To illustrate simply, when we visited Lisbon, Portugal we took some time to research the area and came across information about the gentrification of Lisbon and the struggles it has faced due to tourism. Because of this, we knew we shouldn’t book an Airbnb in this city and consider walking or Uber as our primary forms of transportation during certain hours of the day rather than potentially impeding the locals when they are trying to get to or from work.

Learn The Language

If you are planning to visit a country that’s primary language is not the language you speak, consider taking some time to learn some basic phrases in that language. Not only will it help make your travel smoother, but it will also show that you care about the place you are visiting, more than a traditional tourist.

One way you can learn some key phrases is by downloading Google Translate and downloading the language of the country you’re visiting. Google Translate allows you to listen to the way words are pronounced but is also handy because you can take photos of items to translate or even to voice to text.

Download Helpful Apps

Speaking of apps, there are a number of generic travel apps that can assist you while on your next vacation, but sometimes there are also specific apps that can be used in the country or place you’re visiting. We’ve mentioned some in this post but you can also take a look at our article about the best apps for travel to gather a few more ideas.

Determine Specific Needs for the Place(s) You Are Visiting

United States Passport on a map - travel itinerary planner
United States Passport

Perhaps the most important part of all of this is deciding what specific documents or information you’ll need in order to travel to your destination. Don’t skip out on this research because it will only take you a few minutes of your time.

  • Visa Requirements: Do you need a visa when traveling to this country? How do you obtain a visa for “x” country if you do need one?
  • Passport (plus a copy!): Do you need a passport? Is your passport up to date? Do you have a copy of your passport? – Many countries require you to have your passport on you at all times but you might consider having a copy on you instead while keeping your original in a locked hotel safe.
  • Current Driver’s License: Is your driver’s license near its expiration? Is your address current?
  • International Driver’s Permit: If you are planning to drive in “x” country, do you need an International Driver’s Permit?
  • Medical Insurance Information: Make sure to bring copies of your medical insurance cards and call your insurance company to see if they are valid in the country you are visiting (some are, some are not).
  • Driver’s Insurance Information: Again, if you are planning to drive, bring a copy of your driver’s insurance card and determine whether or not they will cover you in the place you are visiting. If not, consider alternate insurance through your rental provider.
  • Trip Insurance Information: Keep a copy of your trip insurance information with you so you know what to do in case of a crisis and what your benefits are.
  • Doctor’s Visits and Vaccine Information: Research to see if there are any additional vaccines you will need in order to visit “x” country that is different than the typical routine vaccines. If you take any medication prescribed by a doctor, you might also need him/her to sign off or write a doctor’s note explaining the medication depending on where you are visiting.

What To Avoid In Your Travel Itinerary Planner

We can attest that travel doesn’t always go as planned. You might get stuck in a typhoon in Hakone or get horrible food poisoning in Fiji (real-life situations, people!) Because of this, it’s best to be flexible with your travel itinerary planner. Be prepared, but still willing to make changes. Make sure you avoid overplanning your activities and restaurants. Instead, try to get to the activities you can and have a few restaurant ideas so you have options in case some don’t work out.

We hope this information is helpful when planning your next vacation! We’d love to know what other information you find helpful when planning a trip.

Ever have trouble deciding where to begin when planning your trip? In this travel planner we'll cover the best way to make your next trip itinerary, how to save money for travel, find cheap flights and more.

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