How to Plan a Trip in 17 Simple Steps

Have you ever been overwhelmed by the idea of planning a trip because it seems too, well... overwhelming?! 

There's a lot to think about when planning travel: from getting a visa, to figuring out transportation, to booking accommodation and getting local currency, it can be downright stressful.

And it's a bit contradictory, right? Stressing out over planning what is supposed to be a relaxing vacation. We've definitely been there. Many times, in fact. 

But we've learned our share of lessons along the way and now we're here to help. 

In this article, we'll show you how to take the stress out of planning a trip, by laying out a simple 3-part plan that'll ensure you don't forget anything.

We’ll show you how to take a travel daydream and turn it into reality. 

So whether you're planning a 2-week getaway or a journey with no end date in sight, these steps will take you from the brainstorming phase to stepping foot into your hotel room. We think you might actually fun planning your next trip. That's a dare.

Alright, take a deep breath, because we're digging right in!


Step 1: Get the Basics Down: Where, When, How Long?

First, you'll need to figure out the where, the when and the how long.

Start by answering the following questions:

  1. Where do you want to go in the world?
  2. When do you want to go there?
  3. How long do you plan to travel?

Do Your Research

Don't forget to do a little digging and make sure that the time of year you plan to travel is optimal. We have failed to do our research a couple times and it ended up really affecting our trip.

What will the weather be like?

Will it be rainy season? Hurricane season? Super-duper-unbearably hot?

Example: We traveled in India during the hottest months of the year and literally could not do much outside some of the days because it was 110 °F (43.3 °C). After that, we vowed never to make the mistake of traveling without really understanding the weather first.  

Is it high tourist season? 

Will it be hard to get a hotel because it's peak season? Will the lines and crowds at tourist attractions be ridiculous? 

Example: We visited Croatia in July - its busiest month of the year - and found ourselves super frustrated with the crowds and jacked up prices. We ended up shortening our time there because we were not enjoying it as much as we expected.

Croatia in July was PACKED with tourists. If we had to do it over again, we would not have visited in high tourist season. A little research could have told us that July is probably not the best time to visit if you want to avoid the crowds!

Check out this website...

Hold up! Before you start a Googling storm, we've got some good news: There is a website that makes this process so much faster!

Travelendar (combination of travel + calendar) is going to be your best friend because all the research has been done for you!

You can use this tool a few ways:

  1. If you know WHERE you want to go, Travelendar will tell you what time of year is best to visit.
  2. If you know WHEN you want to travel, Travelendar will show you which destinations are best to visit during that time.

But don't worry if you don't know WHERE or WHEN you want to travel... Travelendar is also a great place to gather inspiration.

There is a comprehensive calendar of events and festivals around the world.

How cool is that?! 

And it gets better.  You can choose to view the events by location on a map (totally my style), or if you're more like Ben (type-A-ish and super organized), you can see everything laid out on a calendar

These events span all destinations and interests: from European music festivals to cultural celebrations to naturally occurring events like the migration patterns of wildlife in Africa. When you find an event that interests you, click on it to learn more.

However you decide to use it, Travelendar is a great tool to help you in the first travel planning stages.


Okay, now that you know where and when you are traveling, it's time to really delve in and get the logistics of your trip sorted out.

Step 2: Come up with a travel budget

This step might sound scary, but we've broken it down for you so you can create your very own customized travel budget. We're even sharing exactly how we travel cheaply.

Step 3: Start putting it on the map

Literally look at a map, and start circling all the cities, towns or attractions you want to visit. Look on Instagram for inspiration. Don't limit yourself. What do you want to do? What do you want to see and experience? When planning a route, we typically look at other trusted bloggers recommendations. We figure out how many nights we can stay in each city and how we’re going to get from city to city. We have many itineraries on our Itineraries page where you can see examples of our travel routes and recommendations. Also take a look at Lonely Planet travel guides

Step 4: Pace yourself

Thinking about your pace will determine how many of the places you circled above you'll realistically be able to see. Do you want to pack in as much as possible, or do you want to choose a couple places and really get to explore them? Do you want to travel slow and take in the culture to really understand how locals live? Or do you want to tick places off your list and move from city to city, seeing as much as you can? Maybe a happy mixture of slow and fast? This all depends on the amount of time you have and your budget.

Step 5: How much to get in?

Next, investigate if you need to obtain a visa for the country or countries you’re traveling to. You may not need one for the first country you arrive in, but will you need one for the other countries in your trip? Can you get a visa online, visa on arrival, or do you need to get it in your home country? For instance, if you're traveling to Vietnam, Americans need to get a visa ahead of time (and here's the best and cheapest way to get one).

If you don’t know if you need a visa, check out your home country’s visa websites:

Step 6: Leaving on a jet plane

You know where you want to go? Check. Have your visa? Check. 

Now here comes our favorite part: It's time to book a flight!

Where will you fly into? Are you going to make a loop and fly out of the same airport? Or are you departing out of a new place? When searching for a flight we like to use Skyscanner first because it allows you to search across the entire month to find the cheapest flight.


Tips for getting the best deals on flights:

  • Know when to buy. Depending on where you are flying to and from, there are different recommendations for how far in advance you should buy your flight. 

This graphic from CheapAir illustrates how far in advance you should purchase flights for the best deals. This map is based off of flight originating from the U.S. Read more on Business Insider here.

  • Play around with breaking the flight up. For example, instead of searching for a flight from Minneapolis to Japan, we'll search Seattle to Japan. Then we find a flight from Minneapolis to Seattle. This allows you to have a layover in a cool city, and can be a lot cheaper.  
  • We always compare the price to other search engines like Kayak and Google Flights.  
  • When searching for flights, open an incognito browser window (Ctrl+Shift+N or Command+Shift+N).
  • Practice. By spending a lot of time looking at flights, you'll know what the average prices are. You'll know how to spot a good deal, and you'll know when you're paying too much.
  • Sign up for price alerts. Many search engines allow you to sign up for alerts between destinations. You'll get email notifications when the fare goes down, so you can jump on it!
  • Sometimes airline companies mess up on prices and you can pounce on the deal to get crazy cheap tickets. Stalk these mistake fares on Secret Flying for the lowest prices. 
  • There are tons of credit cards that give you miles for purchases. Our favorite is the Capital One Venture card because it's the best all-around card we've found for travel and points. If you're inclined to get an airline credit card, think about the major airlines at your home airport. You'll most likely be booking flights with that airline so might as well rack up the points. 
  • Don’t forget to sign up for the frequent flyer miles program with flight you choose. Many airlines are part of a broad network and the miles are sometimes transferable.

Flight Tip: Make sure you think about the arrival time at your destination. The cheapest flight might get in at 2 in the morning and you’ll have to wait for hours for your guest house to open. Or on the flipside, if you depart super early in the morning and you’ll have a difficult time hailing down a taxi that early.

Step 7: Booking Beds

Depending on how long your vacation is you may choose to book all your accommodation ahead of time or none at all.

For instance, if you only have two weeks, it might be best to arrange your hotels or hostels online so you don’t waste precious time trying to figure out accommodation when you'd rather be exploring. Plus, you don't want to run the risk of everything being booked up! 

If you're traveling long term, however, you may just book a few days at a time. Or you may prefer to wing it and walk into hotels once you arrive in a town.

Depending on where in the world we're traveling, we switch up our booking sites. Here are our favorites:

Step 8: Please, please don’t forget travel insurance!

Even though you might be safer abroad than in your home country, accidents happen everywhere and you should always be covered. We never leave home without travel insurance and neither should you.

One of the most popular travel insurance companies is World Nomads. They cover anyone worldwide and are extremely easy to use. We were covered by them when we trekked to Everest Base Camp and were every happy with our experience. Fill out the info below to get an instant quote:

For more information on how to pick a policy and what we look for in travel insurance, check out our detailed article here.

Step 9: Where to first?

The first few hours in a new country can be a little overwhelming (and the most likely time to get scammed). That’s why you should have a plan of how to get from the airport to your hotel (or wherever you're headed first). We typically write down the address (in the local language and in English) of our first hostel/hotel in a small book so we can show taxi/bus drivers, that way we don't fumble over mispronouncing street names. 

Book transportation ahead of time or get specific instructions of how to find public transport. Read our travel tips, other blogs, or guide books on what is the best means of transportation in the specific country you're visiting. If you have a plan and know what you’re doing, you'll start off your vacation on the right foot.


Now that you've got all the big planning things check off your list, it's time to nail down the little steps.

Step 10: Register on your country's Smart Traveler program

For Americans, you should sign up for the Smart Traveler Enrollment Program (STEP). Through STEP you'll get emergency updates that would affect your travels, such as bad weather or civil unrest or protests. It will also give you easy access to your embassy in the country you're visiting. Lastly, if anything bad were to happen to you on your travels, you'd be easier to track down. Check your country's travel department for similar programs. 

Step 11: Scan your documents and email yourself a copy

Scan a copy of your passport and any credit cards you're bringing, and email it to yourself. Do the same for your travel insurance documents and receipts of the valuables your carrying. If anything happens to these while you're traveling, you'll have an electronic version.

Step 12: Learn the language (at least a few phrases)

We're not insinuating that you must be able to have a conversation in the local language before visiting a foreign country. But learning a few key words or phrases shows locals that you are trying, and people usually respect this. You'd be surprised how far learning "hello" and "thank you" can get you. Some other helpful words to learn no matter where you are traveling are: "bathroom", "delicious" and "beautiful". And don't for get about numbers. Write down the numbers 1 through 10 in a small notebook and translate them. Knowing a few numbers makes it a lot easier to order at restaurants. 

If you have any allergies or medical conditions, it's a good idea to write it out and translate it to the language of your destination country. For instance, "I am a vegetarian," or "I am diabetic". Print it out in the local language (and the phonetic spelling) and carry it in your wallet. It will definitely come in handy. 

Step 13: Think about your electronics

A quick Google search will show you what type of outlets you'll find in the country you're visiting. Here's a great website for electrical outlets. Look at the voltage too, and check the compatibility with any electronics you're planning to bring along. A great purchase is the travel converter with adapters

Step 14: Refine your Manners

A little research can go a long way. Certain gestures you might use everyday, like a thumbs up or okay sign, are offensive in some cultures. Avoid awkward situations by researching some basic manners in the country you're visiting. 

Step 15: Know common scams

While you're in research mode, do a quick search of common scams in your destination. Being aware of popular scams is often all you need to avoid falling victim.

Step 16: Download some helpful apps

Google Translate: Type in something you want to say, and it'll translate the phrase into any language you select. You can even take a picture of a menu written in an entirely different language (like Korean, for example), and it will translate what is written. It is amazing!

Google Maps: Before going to a new location, we typically load the destination in our Google Maps app. If you have your GPS turned on, the app will show your current location with a blue dot even when you don't have phone service or WiFi. This is super helpful if you're on a long bus ride and want to know exactly where you are, or when you're lost wandering around in a big city. 

Convert: This app makes it easy to convert anything from currency to distance to temperature. (Super handy for Americans unfamiliar with the metric system.)

Time Buddy: If you're traveling on the other side of the world, this app makes it super easy to figure out time difference between where you are and your home country.

Trail Wallet: Yeah, yeah, I know, we've talked about this one a lot. But it has seriously changed how we travel. This app converts seamlessly through currencies and shows you exactly where you are in regard to your budget. Download this app and you'll be able to travel longer. Seriously. 

Step 17: Have a plan for currency

On long-term trips, we typically withdraw money from a local ATM as soon as we enter a new country. We've found we usually get a better rate at ATMs than from currency exchangers (and we don't have to worry about getting scammed). Our Charles Schwab card (more info here) reimburses all ATM fees, so we only take out small amounts at a time. If you're going on a shorter trip, it might make more sense to order the currency from your local bank before you leave home. Whatever your preference, be sure you have a plan for obtaining the currency of your destination.

Wow, I know that looks like a lot. But it's pretty simple, all the information is out there for you to find and explore. If you have any questions or comments about how you should plan your trip, please write them in the comments below and we will answer them.