How to Plan a Trip: A Detailed Travel Planning Guide

Apr 8, 2020

Looking for the best tips on how to plan a trip? Our step by step travel planning guide goes through our exact process of planning our trips, including our travel itinerary template, so you can plan your next trip easier!

It’s no secret that we love planning trips! We love researching for hours upon hours, digging into everything a city has to offer, learning tons, picking spots we want to check out, and crafting the perfect itinerary. 

We are definitely itinerary-based travelers vs spontaneous travelers (although we’re trying to leave more time for spontaneity during our trips!) and we’ve found that putting in the work to plan a trip beforehand can dramatically change the outcome of a trip. 

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There’s no wasting time wondering “where should we eat?” or driving all around town from spot to spot because we didn’t realize how far things were. Instead, we show up with a plan and get to enjoy where we are. Granted, things don’t always go according to plan, but we definitely feel like it sets us up for success!

We originally created this blog to help eliminate some of your headaches when you plan a trip. It can be daunting to figure out how to fit an entire city, state, country, etc into X days. 

Our travel guides in particular are perfect for those who want a solid list of things to do, places to eat, etc. already organized into a well thought out itinerary. Our goal is to do all of the research for you so you can plan your perfect trip without spending hours and days scouring the web.

However, we haven’t been to every city in the world, so we may not always have a travel guide for you. So we wanted to create a travel planning guide, with our step by step list of how to plan a trip, including our travel itinerary template, so you can plan an epic trip and make the most of your time in any destination!

Looking for more travel planning tips? Check out these posts:

Note: this guide contains affiliate links, which means that if you use the links provided and make a purchase, we get a small commission at no extra cost to you. We will only ever recommend products we truly love, actually use during our adventures, and think you can benefit from too!

Step 1: Choose your destination

The first decision when you plan a trip is often the hardest: where should you go?! If you’re like us, we want to visit as many new places as we possibly can, but we also love visiting places that are special to us. Trying to make the decision of where to spend our precious vacation time and limited travel budget sometimes feels impossible!

While we don’t have all of the answers of how to decide where to go, here are a few things to consider.

Type of trip

What kind of trip are you looking for? Do you want to be in a big city? Hang out at the beach? Go for tons of hikes? Or all of the above? Our first task when figuring out where to go is to think about the activities and vibe we are looking for during our next trip.

If you’re having a hard time deciding, some of our favorite destinations are:

  • The Dolomites: The Dolomites are full of adorable small towns, hikes, and epic scenery! It’s absolutely gorgeous and we hear it’s cheaper than the Swiss Alps.
  • Matera, Italy: The smaller town, less tourists and crowds, unique cave dwellings, and crazy history made Matera one of favorite spots in Italy!
  • Vancouver, BC: We used to visit Vancouver all the time when we lived in Seattle. The city is beautiful and there are so many outdoor activities just minutes from downtown.
  • Scotland: We visited Edinburgh and the Isle of Skye and think they are some of the most underrated destinations. Both were jawdroppingly beautiful and have tons to see and do!
  • Seattle: Seattle is our favorite city in the US! We lived here for three years and loved it so much. There are so many things to do, including hikes, lakes, beaches, city activities, and delicious food!
  • Hawaii: It’s no secret that Hawaii is one of our favorite places in the world! We have been to all four major islands, some more than once, and each one is amazing!
  • US National Parks: Want to see some of the best nature in the US? Visit a National Park! Some of our favorites have been Yosemite, Zion, Grand Teton, Yellowstone, Big Bend, Olympic, and North Cascades.

Timeframe

Is there a certain time of year that is easier for you to travel for work or other reasons? For us, it’s the summer and winter, which can influence where we go. If we don’t want to be cold in the winter, we’ll use that time to go somewhere tropical, and on the flip side, if we want a break from the heat in the summer, we would head to somewhere a bit cooler (or below the Equator).

Peak Season vs. Shoulder Season

Some destinations have very clear peak seasons. If crowds are not your thing, try looking for destinations that will be having their shoulder season (the months between the busy season) during the month you want to travel. The weather may not be as perfect during “shoulder season, but you can save a ton of money (and headaches!) by traveling during the off-peak times.

Flight Deals

We will share some of our tips for finding flight deals in Step 3, but one thing to consider when deciding where to visit is to see where you can get a decent flight deal. We have sometimes made last minute trip decisions and visited somewhere we didn’t plan to visit so soon because we got a good flight deal. 

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Specific Attractions or Events

Is there a specific thing you want to see or do in a destination? For example, do you want to attend a music festival in a specific city? See the cherry blossoms in the spring in DC? Want to drive the Going-to-the-Sun Road in Glacier National Park?

Sometimes planning a trip around a specific attraction or event can make the decision a bit easier since you have a limited time to take part in that activity.

Step 2: Make a Travel Budget

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After we have an idea of where we want to go, our next step is to make a travel budget. We try to think of every expense we will have on that trip, from flights, lodging, a rental car, dog sitter, food, activities, gas, and more. This helps us get an idea of how much we will spend and to see if we can realistically afford the place we want to visit. It also keeps our wallet in check when actually on that trip!

We have a travel budget template that we use to not only plan out individual trips, but our trips for the entire year. This helps us see how much we want to spend on trips vs. how much we will be saving to travel.

To see how we afford to travel + our tips to save money to travel and while traveling, check out this blog post!

Step 3: Track and Book Flights

Flight

Once we have a good idea of where we want to go and how much we want to spend, we start trying to find cheap flights! We have a few favorite tools we use to find flight deals, which we’re sharing below.

To get a more detailed look into how we find affordable flights, including a tip we used for our Italy trip to save us over $1,000, read our Fly for Less: Tips for Finding Cheap Flights blog post!

Google Flights

We love Google Flights! This free tool lets you plug in where you will depart from and where you want to go and see lots of flight options from tons of different airlines. You can then track specific flights that work well for your schedule or airline preference. You’ll be notified anytime the flight goes down or up in price, which can help you have a better idea of when it’s time to pull the trigger.

If you’re still stuck in Step 1 and unsure where to go, their explore destinations tool is very helpful to see what destinations are cheapest to fly to from your home airport on specific dates!

FareDrop

If you’re feeling more open on when and where you want to travel and just want a great deal, our favorite paid tool is FareDrop, which allows you to pick the departure airports you want to be alerted about, which destinations you want to travel to, and which months you want to travel.

FareDrop costs $47.88/year (if you use our link you’ll get 2 months free!), which seems a bit pricey, but we get tons of deals weekly! We have yet to pull the trigger on them, but hopefully soon!

Hopper

Another tool we have used a lot in the past is Hopper. Hopper is a tool that helps predict flight costs and lets you know when the right time to book is. Nothing is worse than when you buy a flight and then the next week it has gotten a lot cheaper!

Scott’s Cheap Flights

Scott’s Cheap Flights is both a free and paid tool ($49/year) that will alert you about deals and mistake fares (when an airline accidentally publishes the wrong fare). Similar to FareDrop, you choose your home airport (and neighboring airports) and get deals from those airports. Or you can see deals worldwide! We only use the free tool of Scott’s Cheap Flights and we get pretty great deals! If you pay for their Premium version you supposedly get even better ones. 🙂

Skyscanner

Skyscanner is another very popular tool for finding cheap flights. We have seen flights cheaper on Skyscanner than most other websites. Once you find a cheap flight, you book it through one of their travel partners. The only downside for us is that we typically cannot get that price with our credit card points, which we would rather use to book travel (since it’s free!).

Use Points

By far our favorite way to book flights is with our credit card points! We have saved thousands of dollars by using credit card points and the best part is that we earn these while making our usual transactions, like the grocery store, bills, or coffee. The points add up fast depending on which card you have, so it’s not too hard to get free flights!

We currently have 4 travel credit cards: Chase Sapphire Reserve, American Express Platinum, Capital One Venture Card, and the Alaska Airlines Card and each one has its pros and cons.

For more details on our favorite travel credit cards, the best benefits, and how to pick the right one for you, check out Our Favorite Travel Credit Cards blog.

Step 4: Book your accommodations

After figuring out flights, it’s now time to find a place to stay! Once we have a general idea of the dates we plan to travel, we start looking for Airbnbs and other accommodations, saving any spots that catch our eye, and then as soon as our flights are booked, we book our lodging. Here are a few sites we love for finding accommodations!

Airbnb

We are huge Airbnb fans! We probably stay in Airbnbs 95% of the time when we travel. We love getting to stay in more local areas, having more space, being able to cook, and it’s usually cheaper than a hotel!

PS: If it is your first time staying at an Airbnb, click this link to get $40 off your first stay!

TripAdvisor

TripAdvisor is our go-to site for hotel reviews! It has helped us make the decision of where to stay (or where not to stay) many times. 

Booking.com

Booking.com is our favorite website to book hotels. Their prices are usually some of the best out there! Another really cool thing about Booking.com is that they have vacation rentals (like Airbnb) as well. So if you want a one stop shop to browse hotels and rentals, they’ve gotcha covered!

Step 5: Book your transportation

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Depending on where you’re visiting, you may need to book additional transportation. 

For rental cars, we typically book through rentalcars.com. They have a price match guarantee, so if you find a better price somewhere else, they’ll match it!

We also have used Costco to book rental cars before. Their prices tend to be the best out there, but you do have to be a member or have access to a member’s account. It’s okay if the name on the car is different than the member’s name, so if you have a family member with a Costco membership, ask them if you can use it! 

Note: our travel credit cards give us rental car insurance around the world, so we do not opt into the additional insurance when renting a car. Make sure to check in advance to see if you’re covered! Also, make sure to book an automatic car in Europe if you don’t know how to drive a manual. 🙂

For public transportation, like trains, subways, and buses, purchasing in advance varies depending on where you’re going. During our Italy trip, we booked most of our trains and buses from city to city in advance to take advantage of a lower price. But in most US cities, like NYC, you just get your tickets at the station before boarding your mode of transportation. 

When looking for trains, subways, and buses, we typically start our search with Google Maps to see the routes and find out which company runs that route. Then we go to that company’s website to see fares, schedules, and to see how to purchase tickets. 

Step 6: Research, Research, Research

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Our next step when we plan a trip is to research like crazy! We spend days and even weeks reading blogs, watching vlogs, and scouring the internet for as much information as we can about a destination, including where to eat, things to do, and any helpful tips! As we research, we create a Google Doc and write down the spots we find by category (food, coffee, landmark, activities, etc).

This part can be a bit overwhelming because there is tons of information out there and it can be hard to figure out what to prioritize for your own trip. We like finding a mix of popular spots with thousands of reviews, as well as more local spots with maybe less reviews overall, but very positive ones. And if we see a recommendation mentioned on multiple blogs and websites, that spot usually goes higher up on our “must-do” list. 

There are a handful of tools that we use every single time we plan a trip, each for slightly different reasons. 

Pinterest

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Pinterest is an amazing resource for travel planning. It’s a massive search engine and a great way to quickly find tons of blogs about a destination you’re going to and to see what real people recommend. We typically create new boards for a country or region and then fill it up when we start to dream about a trip we want to take. Once it comes time to actually plan it, we will head to that board and open all of the blogs we saved, write down common things people recommend and then research some of the lesser known options.

We personally prefer Pinterest over Google searching because Google tends to feature less bloggers and more Yahoo/Frommer’s type sites, which are fine too, but we enjoy personal blogs more. We have actually discovered some of our favorite travel bloggers that we may not have ever found on Pinterest, so it’s also a great way to find more people you click with and want to follow! 

If you’re not already following us on Pinterest, come hang out with us here. We love to share pins from all over the world!

TripAdvisor, Yelp, and Google Reviews

Okay, these are definitely the most obvious, but they are high on our list when researching different cities! We know that some people are leery of review sites, but we personally love hearing from regular people about their experiences at a restaurant, attraction, etc.

We think that if you look at a wide variety of reviews for a place, the good and the bad, you can usually feel pretty confident (or not confident) in making it a stop on your trip. TripAdvisor also has forums where people can ask questions and others can answer and these can be really helpful to read, especially if you have questions that others have already asked.

One thing we have noticed is that Yelp is big in the US for restaurants, but TripAdvisor and Google Reviews are much bigger abroad. For our Mexico City trip, we relied heavily on Google Reviews, as the other two sites hardly had any reviews for restaurants. So make sure to look at all three sites to get a better idea of what a restaurant or attraction is like.

YouTube Vlogs

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YouTube is our new favorite way to research for trips. It’s like reading blogs, but actually getting to see the experiences! Some of our favorite travel vloggers to watch are: Kara and Nate, The Endless Adventure, and Mark Wiens for awesome food videos! We watch travel vlogs every night and always mark down good spots to check out whenever we go to those destinations in the future.

If you want to follow along on our adventures, you can subscribe to our YouTube channel here!

AllTrails and Hiking Websites

We love hiking during our trips and one of the best resources we have found for trails is AllTrails. What we love about AllTrails is that it has trail information, such as miles and elevation gain, as well as hiker reviews, for trails all over the world!

We have used AllTrails for hikes all around the US, as well as in Italy and Canada, and it has always helped us gain a better understanding of what to expect on the trail, as well allowed us to follow our progress on the trail map.

There is a free version, but we recommend paying for the AllTrails Pro app ($30/year) to have guaranteed offline map access, off-route notifications, and family and friend notifications.

Beyond AllTrails, we love finding local hiking websites. When we lived in Washington, we used the Washington Trails Association website for every hike. Similar to AllTrails, it has reviews, photos, and hike information, but it is typically more detailed.

Instagram 

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Instagram has opened our eyes to sooo many places in this world! The popularity of the app is both a good thing and a bad thing, as some places are becoming Instagram famous and are definitely being visited too much and/or disrespected, but it is also showing us how beautiful some lesser known places are.

Similar to Pinterest, you can bookmark posts on Instagram and even organize them into different collections. We use this feature to save spots that look cool to visit in the future. However, we love Instagram more for the ability to see places in real time. 

When we know we are going to visit a place, we will look up the locations on Instagram (both posts and stories) to see what it currently looks like, crowds, and to try to find cool photo spots. We did this a ton in Washington to plan our hikes and to see if there is still snow, what the hike looks like in different weather conditions, etc. It’s also helpful to find out if a specific spot is under construction *cough* Big Ben *cough*. 

Don’t follow us on Instagram yet? Head on over to our Instagram page to see even more adventures!

Family and Friends

If you have friends or family members that have visited the destination or live in the destination you’re heading to, ask them what their favorite spots are! These recommendations can often be the best, especially if you know and trust that person’s taste.

One of the best food recommendations we ever got was from one of our best friends. She told us we had to go to La Romana for gelato while in Rome, which wasn’t originally on our list, and it ended up being our favorite gelato during our entire two weeks in Italy! We owe her a scoop (or two) of gelato for that recommendation!

Step 7: Google Maps

Google Maps

After we make a big list of all of the restaurants, landmarks, activities, and tours that catch our eye while researching, our next step when we plan a trip is to look at Google Maps to see where everything is in relation to each other.

We try to structure our days in a way that we don’t have to travel all over town, but instead stick to a general area so we can maximize the time we have to explore. We suggest making a map on Google My Maps so you can pin all of the locations and then start to group together the things that make sense to do together. This will help you big time with Step 8!

Step 8: Make your itinerary (with our travel itinerary template!)

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So you’ve done your research, written down some spots, and have seen where they all are on a map…now what? Our next step when we plan a trip is to start organizing all of our must-do and must-eat places into an itinerary.

Our friend Callie created the most detailed, helpful travel itinerary template in Google Sheets that has helped us SO much with our last few trips. We told her we were going to have to share it on our blog because it was very useful and would help so many people, so a BIG thank you to Callie for creating this!

We like creating an itinerary because typically our trips are short and we want to maximize the time we have in every destination. We realize not everyone likes to have as structured of a trip, so feel free to modify the template to fit your needs better! We always recommend being a bit flexible in case the weather is bad one day, you are exhausted and need more rest, or things just don’t go according to plan (which happens often when traveling)!

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With this travel itinerary template you can list out the activities for your day in order, write down addresses, add notes (such as: arrive before X time to avoid a line, how to get somewhere, note that it’s cash only, etc), add helpful links, keep track of costs, have a rough estimate of timing for each stop, etc.

It’s also great for collaborating with others! We have used it for our couples trip to Arizona to make comments back and forth and decide what we want to do. 

You can download our travel itinerary template here. Note: To use the sheet, please go to “File” and then “Make a Copy” to create your own version! We included an example as well so you can see how we would fill it out.

Step 9: Book any tours, activities, and reservations

Once you have a good idea of your itinerary, start locking down any tours, activities, and meal reservations for a time slot that works best for you!

Tours + Activities

When we were in Italy, we booked our tours and entrances to museums in advance to save a little bit of money. While we typically had to commit to a timeframe, it helped us structure our days better and ensure we had a tour to go on. 

For attractions where you can get early admittance (like the Vatican) or they get busy during specific times, booking ahead of time can also help you beat the crowds.

Not sure where to find tours? We’d recommend looking on TripAdvisor and Airbnb Experiences! (First time Airbnb user? Use our link to get $15 off your first Airbnb Experience!)

Reservations

If during your research you find that a reservation is heavily recommended for a restaurant, set a reminder on your phone for a month or so beforehand to give them a call and secure a table. When you have limited time to explore on a vacation, the last thing you want to do is wait in line for a restaurant, especially if you’re hangry. 🙂

Step 10: Prepare for your trip

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Photo by Christian Dubovan on Unsplash

Depending on your trip and where you’re going, there are a few extra things to consider looking into before you travel.

Book luggage storage

The only downside about staying in an Airbnb vs. a hotel is that sometimes you’ll arrive before check in or have time to explore after check out and have nowhere to put your bags. We have used Luggage Hero or Bagbnb to find safe places to leave our bags while we explore before or after checking out. 

Get travel insurance

If you’re traveling abroad, it may be worth looking into travel insurance. We hear that World Nomads is a good option for travelers and covers trip cancellations, baggage issues, medical emergencies, your gear, 200+ activities, and more!

Disclaimer: we have yet to use international travel insurance, but plan to look into it for future trips!

Look into driving rules

In Italy, we had to get an International Driving Permit. You can get this from AAA for only $20. We aren’t sure how many countries have this rule, so definitely check the road rules beforehand to avoid getting a ticket or having issues getting your rental car.

Find out if you need a Visa

Depending on where you are visiting, you may need to get a Visa to enter. This website shares the Visa requirements for US citizens for both business and personal trips for every country! We suggest checking this right after booking your trip to see what the requirements are and how to obtain one.

Check vaccine requirements

Some countries require that you have certain vaccinations before your arrival. You can search the destination you are visiting and see if it requires you to get a vaccination on the CDC’s website. We suggest checking a couple months in advance, as different vaccines have different timeframe requirements to get them.

Get local currency

If you’re traveling to another country, make sure you look into the local currency. We typically will order some foreign currency from our bank before our trip (try to do this at least a week before you leave, as it takes a few days) just to make sure we have some on us when we land.

After we land, we will try to find somewhere to get additional currency during the trip. Make sure to research where the best place is to get this currency. In Italy, for example, the best place to get Euros was from bank ATMs—the ones in actual banks, NOT the ones just on the street in the big cities, as those will charge you massive fees. 

You may also need coins for restrooms in some countries, so plan to have coins, as well as bills, handy for your trip.

Also, let your bank know you’re traveling abroad to avoid them thinking there is fraud with your card.

Learn the local culture and etiquette

It’s important to understand the culture in a different country or region, especially if something that is considered inoffensive in your home country is considered offensive elsewhere. 

Tipping is another important thing to look into. In the US, tipping 20% is pretty standard, but in Europe, tipping is not common at all. 

Figure out your internet plan

If traveling abroad, we highly recommend getting an internet plan for your phone or SIM card. Relying solely on wifi can be a bit stressful at times and it’s worth the cost to be able to use your phone freely. 

We have always bought AT&T’s International Day Pass, which is a bit pricey, but it gives us the same data amount that we have back in the US. They also have an AT&T Passport Plan, which lets you pick a set amount of data for your entire trip.

We also suggest downloading offline Google Maps so you can use maps without eating up data.

Download Google Translate

Google Translate has been a lifesaver when traveling internationally! We used the conversation feature to communicate back and forth with our Airbnb host in Italy and it not only was so much fun, but it allowed for us to converse even with a huge language barrier!

Let someone know your plans

Make sure a family member or friend knows your plans just in case something were to happen. We always send our parents our flight info, as well as our itinerary, just so they are aware of what we’ll be up to during our trip.

Step 11: Pack for your trip

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Do you pack in advance or are you a last minute packer? We used to start packing days in advance, but lately we procrastinate big time! Regardless of when you pack, figuring out what to bring on your trip, while also not forgetting anything important, is hard! 

Check out our top travel items and packing list to see which items we cannot travel without and to download our packing list, which includes common items and some easy to miss items, that you won’t want to forget!

Our most important packing tip: Don’t forget your passport and make sure you have an adapter if traveling abroad! We love this one!

Step 12: Have a blast! 

After all of your hard work, it’s time to enjoy the trip! We hope that you found this travel planning guide helpful and that it’ll make it easier to plan a trip in the future! 

Ready to plan a trip?

Pin this step by step travel planning guide to make planning your next trip a whole lot easier!

about us

Hi y’all! We’re Adam, Kathryn, and Kona, an adventurous married couple (+ pup!) living on the road in our self-converted sprinter van! You can often find us driving all around the US and Canada, scoping out the best coffee shops, eating tacos and ice cream (we’re a 5+ taco and 2+ scoop household), and enjoying nature.

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2 Comments

  1. Carol

    Love your enthusiasm. Many carefully thought out ideas. When you post a photo on your blog, it covers up what you wrote. For instance I can only read one Credit card, Chase, the other three are covered by the happy photo of you two. Your three how to plan a trip guides cover up what ever your conclusion/close suggestions? Hope you can fix this as you seem to be very thorough…. I don’t have this problem with my other sites I read regularly. Just thought I would mention.

    Also, you should always have a photo copy of the your passports and front and back of credit cards with your parents In case of problems… You can ge it all replaced many hours /days quicker than without…

    Reply
    • Kathryn Frazer

      Hi Carol,

      I am so sorry you’re having issues reading our site. Everything looks normal on our end, so that’s very odd and we’d love to figure out what went wrong. What internet browser and type of device are you using? We will look into this to make sure no one else has issues like this.

      And thats a great tip about passports and credit cards!

      Reply

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