✈️ Planning a Trip Anywhere in 10 Easy (but Important) Steps

Planning a Trip blog cover image.  Text overlaying an image of a woman walking along the trunk of a slanted palm tree on a white sand tropical beach.

There is an art to planning a trip successfully and stress-free, whether that trip happens to be a week of vacation or a year of backpacking.

In this guide, you will learn how to plan a trip anywhere in the world with a sequential, step-by-step process that is easy to follow.

You will also discover useful resources for things like finding cheap flights, travel insurance, accommodation, and more.

📋 How to Plan a Trip: Overview

A flat lay image showing various travel items ready to be packed while planning a trip including a water bottle, phone, drone, laptop, passport, camera, and cash.

The 10 important steps for planning a trip, in the order you will want to do them, are:

  • Step 0: Decide where you want to go!
  • Step 1: Establish your budget.
  • Step 2: Review current travel advisories and entry requirements (including vaccinations).
  • Step 3: Decide trip length.
  • Step 4: Book flights.
  • Step 5: Research your destination must-dos.
  • Step 6: Arrange accommodation.
  • Step 7: Reserve a rental car (or alternative transport).
  • Step 8: Buy travel insurance.
  • Step 9: Create your itinerary.
  • Step 10: Book tours and activities.

Regardless of whether the trip you are planning is just a one-week vacation or a one-year backpacking trip, you will want to go through each of these steps thoughtfully as you plan your trip.

The remainder of this guide will cover each step listed above in full detail. As you read, you will learn why it is important to move in the order presented while also finding tips and resources for saving time and/or money for each step.

🌎 Step 0: Decide Where to Go

*Click photos for planning guides to each featured destination below

Those of you who already know where you want to go for an upcoming trip can skip directly to Step 1. For the undecided, however, this is the most important thing you need to figure out!

If you are embarking on your first-ever backpacking trip, this decision comes with endless possibilities. Which country, region, or continent is right for you is a very subjective thing as each presents different levels of safety, cost, entry requirements, and preparation, not to mention widely different experiences.

For first-time backpackers, we recommend looking into Southeast Asia as a good first option. Many countries in the area have well-established backpacker routes, with Thailand and Bali being particularly well-established as beginning points for extended visits.

If you are thinking short-term vacation, your best options will be more limited than you might imagine and will be mostly determined by where you live, your available budget, and what climate you are seeking.

The best tropical getaways in the US are the Hawaiian islands for west coasters, as well as Southern California (Palm Springs, San Diego, Los Angeles). East coasters, meanwhile, have the Florida Keys, Miami, and US Virgin Islands as fantastic options.


🍍 Step 1: Review Travel Advisories & Entry Requirements

A photo from the page on the US Government website where travelers will find current travel advisories when planning a trip internationally.

Before you begin making any official bookings, the first step in planning a trip is reviewing the current travel advisories, entry requirements, and visa requirements for your destination.

It is important to do this first to ensure you are going to be allowed to make the journey. Each country and even some states may have unique restrictions in place that can affect your ability to travel, such as visa requirements or mandatory vaccinations.

In addition, there may be some sort of local travel advisory you need to be aware of. These can be anything from natural disasters to civil unrest.

US citizens can find current travel advisories and entry requirements for each country at TravelState.Gov.

British citizens can find foreign travel advice on the Gov.uk.

💲 Step 2: Establish a Budget

A selection of smaller US dollar bills are photographed spread across a wooden table.

Now that you know where you are going and have established that you meet all of the entry requirements, the best next step in planning a trip is establishing a budget.

Knowing how much you have available for your trip or vacation will determine how long you can go for, where you can afford to eat and stay, and which tours or activities you can indulge in.

Before you even begin looking into more details, write down exactly how much you are willing to spend. As you continue through the remaining steps and start booking out the essentials, jot down what you have spent so far so that you know how much you have available throughout.

Flights and accommodation will almost always be the two biggest expense items on a trip.

📆 Step 3: Decide Trip Length

A view of Kihei Beach surrounded by palm trees, with the cloud-covered West Maui mountains looming in the background.

For vacationers, the length of time available for a trip will probably be rigid and limited. For the backpackers, it is more likely to be very open-ended.

Either way, it is good to figure out as accurately as possible how much time you truly have available for your trip.

Remember to account for flight times and distances, time zones, and airport commutes! Seven days feels a lot shorter if you are going to lose two of them just getting to and from your preferred destination!

Knowing how much time you want for your trip may also impact which flights you book and how you are able to spend on meals and accommodation.

🛫 Step 4: Book Flights

Looking out an airplane window with Mt Rainer being framed by the wing of the small plane.

Now that you have laid all the groundwork for your trip, it is time to start actually making reservations and committing to the trips. This starts with booking flights!

We will discuss in some detail how to find the best prices on flights next. First, however, there are a few pieces of advice that are important to consider if you are new to travel.

The shorter the duration of your trip, the more you should look for direct flights TO your destination.

Every extra layover creates extra opportunities for schedule disruptions that can completely undo months of planning.

For example, a delay on your first flight could result in missing your layover, leaving you stranded until whenever the next available flight happens to be!

The journey home tends to be slightly less important for most people, but this is something you will need to determine for yourself.

Of note, weekday flights are nearly always the cheapest. Summer months are nearly always the most expensive.

How to Find Cheap Flights

Screenshot of a Skyscanner flight search demonstrating how users planning a trip to Hawaii can find the cheapest flights.
An example of a flexible flight search with “Cheapest Month” selected.

If you have flexibility in your dates, use SkyScanner to find the cheapest flights possible using the flexible departure features.

This software makes flexible searches extremely easy and looks for the best possible deals for you across all airlines!

Simply type in your departure city in the “From” field and enter the destination you wish to travel to in the “To” field.

Then, search for the cheapest dates within the month you are planning a trip, or even the cheapest ticket available within the calendar year!

📸 Step 5: Research Destination & Must-Dos

*Click photos for planning guides to each featured destination below

Now you’ve got your flights booked, you will want to figure out where you are going to stay. Before you can do that, however, it is good to do a bit of research on your destination and figure out the things you want to do most.

This is important because it will help you determine which area you want to stay in. If you book your entire trip in the north and everything you want to see is in the south, it could become a point of frustration.

One of our favorite planning tricks is to create a personal Google Map and add points of interest to it with all of the things we want to do and see.

Adding stops to a Google map allows us to assess drive times, and concentration of points of interest to identify which areas we’re most interested in. This is useful in deciding where we want to be based and sometimes even steers us towards dividing our time across multiple accommodations.

🛏 Step 6: Arrange Accommodation

Now that you know everything you want to see and do on your trip, the next step of planning (and perhaps the most important) is to book your accommodation.

If you are embarking on a multi-month backpacking trip, you should at least book your first two nights. Most countries require you to fill out a form upon arrival with a stated address where you will be staying, so you need to have one ready.

In addition, it is much easier to have accommodation ready to go upon arrival so you have a home to recover from jet lag and begin the next phases of your trip.

For the vacationers, this will likely be your biggest decision! Accommodation will have the largest impact on your budget and comfort, and likely your entire experience.

Your decision will come down to what you prioritize most. Is it important that you have a place right on the beach, or would you be willing to walk a short distance to save some money? Would you prefer a small but quality hotel room, or a large but modest vacation home rental?

Take your time and carefully consider/compare your options. Below are some of the best places to begin your search:

  • Booking.com
    Lists all accommodation types including hotels, BnBs, and vacation rentals. Often has good discounts, particularly if you have an account.
  • Expedia
    Offers a broad range of accommodation as well as packages.
  • VRBO
    Good for groups. Mainly US-based private vacation rental properties.
  • AirBnb
    Good for quirky stays. Largest variety of private listings, from staying in someone’s home to private rental houses, houseboats, and everything in between.

🚗 Step 7: Reserve Rental Car (or Alt. Transport)

Adam Marland and Sophie Clapton of We Dream of Travel pose on a Jeep under palm trees in Kona on the. Big Island of Hawaii.

Now that you know where you are staying, you need to plan how to get around.

Typically, renting a car is the best option as it provides maximum freedom for exploration. Of course, this varies massively between vacation types and destinations.

If renting a car is necessary and something you are comfortable doing on your trip, RentalCars or Kayak tend to be the best search engines for finding the lowest prices.

When renting a car is not an option, you will have to do a bit of research on your destination to discover what options exist. You may wish to consider booking tours to the attractions you’re interested in if renting a car or taking public transport aren’t options.

Whether you are traveling by foot, bus, plane, or train, be sure to book any essential transportation ahead of time to limit the potential for schedule complications due to sell-outs.

🩹 Step 8: Buy Travel Insurance

Lightning strikes are seen over the hoodoos of Bryce Canyon in Utah in this night photo.

With the amount of flight cancellations and natural disasters that seem to be rampant these days, buying travel insurance is one of the most important things you need to do when planning a trip!

This should typically be done after you have made all of your other arrangements because many travel insurance providers require you to claim the value of the trip you are insuring.

For example, if your hotel and tours allow free cancellation at any time, you may only want to insure your flights and personal health. If, however, you have non-refundable tours and hotels booked, you likely want to ensure the full value of your trip.

🏝 Step 9: Plan your Itinerary

One of the final steps in planning a trip is to figure out your travel itinerary.

At this point, you know where you will be staying, how you’ll be getting around, how much budget you have remaining, what are your must-dos, and how many days are available for your trip.

With all this set in stone, you can begin to establish how you want to spend your time!

Depending on the type of traveler you are, you may prefer a rigid itinerary with a schedule for each day so that you are sure to maximize your time and make the most of it.

Of course, others prefer to wait and see what opportunities come up and where their heart and eyes guide them!

There is no right or wrong, but it is always good to at least have an idea of the experiences you absolutely do not want to miss and to schedule those items. Knowing when and how you will see the “musts” help you plan (or not plan) the rest of your trip.

🎟 Step 10: Book Tours & Activities

The last step in planning a trip is to book those tours, meals, and activities that you have decided on definitively.

If you have followed this guide step-by-step, you should have a good idea of how much budget you have remaining and have established your itinerary. Now, you can start making official reservations for the things that matter most to you.

The first reservations should be the things that are most important to you to experience, especially things that could sell out. Lack of availability could force you to re-arrange your itinerary, so it is best to set those items in place as soon as possible.

We typically book our tours on Viator or GetYourGuide as they allow us to compare multiple different tours from a variety of operators.

🙋‍♀️ FAQs on Planning a Trip

Sophie Clapton of We Dream of Travel poses for a photo at the iconic Isla Bartolome Viewpoint during our 2023 travels to the Galapagos islands.
Click photo to discover the best things to do in the Galapagos Islands.

Below are some of the most frequently asked questions people have when planning a trip.

Simply click the drop-down arrows to reveal answers.

How do you plan a trip for the first time? How do I start planning a trip?

The 10 most important steps for planning a trip (in the order you will want to do them) are:

  • Step 0: Decide where you want to go!
  • Step 1: Establish your budget.
  • Step 2: Review current travel advisories and entry requirements (including vaccinations).
  • Step 3: Decide trip length.
  • Step 4: Book flights.
  • Step 5: Research your destination must-dos.
  • Step 6: Arrange accommodation.
  • Step 7: Reserve a rental car (or alternative transport).
  • Step 8: Buy travel insurance.
  • Step 9: Create your itinerary.
  • Step 10: Book tours and activities.
How do you plan a backpacking trip?

The best way to plan your first-ever backpacking trip is to follow these steps, in order:

  1. Decide where you want to go.
  2. Review travel advisories and entry requirements (visas, vaccines, etc.).
  3. Establish your trip budget.
  4. Decide how long you want to be gone.
  5. Book your one-way flight if possible, roundtrip if necessary.
  6. Arrange your first hostel or accommodation.
  7. Buy travel insurance.
  8. Research your chosen destination(s) and travel route.
  9. Figure out options for getting around.
  10. Create an itinerary (or not)!
How do you plan a vacation?

If you do not have any flexibility with your vacation dates, you will want to first check travel advisories and entry requirements for your destination, then simultaneously book flights and accommodations to ensure there is availability for your exact dates. With these established, you can start making your travel itinerary and any necessary reservations.

If your dates are flexible, begin by figuring out when the cheapest flights and accommodations are available, then plan your trip around those dates!

What is the most expensive part of planning a trip?

Flights and accommodations will almost always be the two biggest expenses when planning a trip anywhere in the world.

If you are trying to save money on a trip, it is best to establish whether you will be spending more on airfare or accommodation so that you know which is more important to find a discount on and to set your travel dates around.

How far in advance should you book a trip?

How far in advance you should book a trip depends on how flexible your schedule is. The more rigid your dates are, the longer in advance you need to arrange flights, hotels, and activities to ensure availability.

Those with flexible schedules can afford to be patient and look for last-minute deals, though this largely depends on the destination.

💬 Final Thoughts on Planning a Trip

Travel photographer Sophie Clapton is seen on a beach at night observing the Aurora Australis, also known as the southern lights,

The two of us work very hard to create these free travel guides to help you plan your dream vacation. If you think we’ve done a good job and would like to say thanks, please consider clicking the donate button below 🙂

We truly hope you have found this guide useful in planning a trip, whether that be the vacation you deserve or your first-ever backpacking adventure around the world!

Now we’d like to hear from YOU!

Was there any information that you found confusing, inaccurate, outdated, or missing?

Or perhaps this is the best guide you’ve found on the topic and had all of your questions answered?

Regardless of your thoughts, we want to hear them! Help us to help future readers like yourself by providing your feedback in the comments below.

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Sophie's passion for travel and photography are outweighed only by her love for animals! Originally from London and now living in the Pacific Northwest, Sophie has traveled to over 30 countries across all seven continents, many of which as a solo female traveller.

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