How to Plan a Trip 101: An Easy Step-by-Step Guide

April 11, 2024

Travel planning can be both an exciting and overwhelming task. Organizing trips and getting the itinerary put together helps to create more anticipation for your upcoming vacation, but it’s easy to feel lost and overwhelmed if you don’t know where to begin. That’s why I have created this easy step-by-step guide on how to plan a trip to help break down and simplify the process for you.

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Step 1: Determine Your Travel Budget

The first step on the travel planning checklist will be to figure out how much you are able to spend on your vacation. Even by just giving yourself a rough estimate on what that looks like will help you while you’re looking to book your flights and accommodation later.

The last thing you want is for any trip’s total expenses to come as a surprise to you later. What your budget looks like may also help determine where you want to go – For example, some long-haul flights may come as a bigger expense than flights for a destination that is closer to you, or at least on your side of the world. (Unless you happen to find a killer flight deal, which we will get to later.) 🙂

Take some time to sit down and have a good look at your finances to determine what your disposable income looks like. Or, depending on your situation and what kind of trip you’re looking to take, you may opt to start setting money aside and build a savings for your vacation. Either way, knowing what your budget looks like will help you in the long run before you start to actually plan your trip and book anything. Something I do for myself, is to keep my personal budget in a Google Sheet doc and update it when needed. It’s an easy way to track your monthly income and expenses, and from there you can determine how much you’re able to set aside in savings and spend as disposable (aka, travel funds!).

Step 2: Check for Flight Deals

I know what you’re probably thinking: Rylie, I don’t even know where I’m going yet. How can I check for flights for a destination I don’t have?

I’m listing this as Step #2 because frankly, finding a great deal on airfare has been the determining factor for most of my travels. Often, your flights will be your biggest travel expense – So finding a great deal here can help you save more for more fun and adventures at your destination!

As a full-time travel agent, I will say that there are a lot of factors that go into determining what airfare prices will look like. Time of year, current events, availability on the plane, etc. So there isn’t necessarily any kind of foolproof method for finding a great deal on flights every single time.

But something that makes this easier (and does all the work for you), is to sign up for programs that email you when flight deals become available. A lot of the time, deals on airfare do not last very long at all, so this also helps you to avoid missing any opportunities by manually checking yourself.

The 2 flight deal programs I use are:

Thrifty Traveler
Going (Formerly known as Scott’s Cheap Flights)

Both include a fee to sign up, but frankly, these have helped me save so much money on airfare over the years (I’m talking thousands), that they are completely worth it.

————— Read More —————

The Ultimate Guide to Finding Cheap Flights

Step 3: Choose Where You Want to Go

Once you have a good idea of what your travel budget looks like, the next step (and maybe most exciting), is deciding where to go! Maybe you already have created a travel bucket list for yourself, with all your dream destinations included. Or maybe, you found a really awesome deal on airfare that you just can’t pass up, and this is your deciding factor.

If you’re still on the fence and can’t decide, here are a few articles I’ve written on destination ideas to spark some inspiration:

————— Read More —————

53 Dream Destinations to Add to your Travel Bucket List

10 Underrated Summer Travel Ideas in the US

Step 4: Research Your Destination

Once you know where you’re going, the next step to planning your trip is to research your destination.

Here are a few things to keep in mind during your destination research:

Best times to visit? And what the weather will look like that time of year
What do prices on food, accommodation, and activities look like when you get there?
Where are the best places to eat and shop?
Any holidays or events that may make a destination more crowded / hike up prices
If you’re going international, will you need a visa? Or vaccinations?
Ongoing conflict at your destination / any travel advisories?
Will you need a rental car to get around once you arrive?
For the attractions you want to visit, check for opening hours and any entrance fees / ticket requirements

Getting to the nitty gritty on your destination and researching all the specifics will help you not only feel more prepared for your trip, but also helps you avoid any potential surprises once you arrive.

Step 5: Determine the Length of Your Trip

After you have researched your destination and have a better idea of what you want to do when you get there, the next step to plan your trip is to determine how long you can travel for.

Determining the length of your trip may be based on several different factors, including your destination, how much time you can take off of work / your day-to-day responsibilities, and your travel budget.

The travel time to and from your destination may also be a factor that helps you figure out the length of your trip. If you are hoping to take a long-haul flight to the other side of the world, you may want to plan for a longer trip of at least a week. Whereas if you want to visit a destination that is close by, you may be able to visit in a weekend or a short trip.

The activities and sightseeing that you want to do at your destination will also help you determine how much time you will need there.

————— Read More —————

How to Travel More with a Full Time Job (& Maximize Vacation Days) in 2024

Step 6: Book Your Flights

So far, you – Have a rough idea of what your travel budget looks like, have chosen a destination, (maybe even found a great deal on your airfare), and know how long you would like to visit. Yay! Now you are ready to book your flights!

If you found your airfare deal using one of the programs I shared earlier, go to the deal outlined there and then find those flights to book directly with the airline. (They will suggest the same thing).

If you weren’t able to find an airfare deal there, that’s okay – I have other options for you.

Use these flight search engines below to scour the web for available flights at any given time:

You can do the same thing for these sites, where once you find the flights you want, search for those exact flights on the airline’s website and book directly with them. Booking directly with the airline instead of a 3rd party site will make things much easier for you, should you need to make any changes to your reservation (life happens).

Step 7: Book Your Accommodations

Now that you have your flights booked and your travel dates set, it’s time to check out your accommodation options.

What you should look for in accommodation may depend on both your travel budget and proximity to the activities and sightseeing you may want to do.

Here are the sites I use to search for accommodation:

Hostelworld – For more budget-friendly options and dorm-style shared rooms if you are looking to meet fellow travelers. You may also find private rooms in hostels that price lower than a room at the nearby hotels.
Booking.com – For deals on both hotel chains and local boutique properties. (This is another site where I would search for what is available, and then book your reservation directly with the hotel.)
Airbnb / VRBO – For rental properties. These are great when you want a more authentic experience and feel like you are living like a local in your destination.

Step 8: Book Your Day Tours & Activities

Now that you have your flights and accommodation squared away, you’re almost done with your itinerary! All that is left to plan your trip is to book your day tours and activities.

Take a further look into the research you did on your destination and reserve any of the tickets and necessities you’ll need for your attractions. You may also want to look into options for a car rental, if you will need a mode of transportation around your destination.

You can also use these sites below to have a look at any available tours or attractions you may have missed in your previous research:

Viator by TripAdvisor – For day tours and activities.
Rentalcars.com – For easy car rentals

Step 9: Pack

Now that you have everything booked, the next step on the checklist to planning your trip is to pack!

Packing for any vacation can seem like a daunting task, as well. But I promise it doesn’t have to be. While you might be tempted to bring everything with you and overpack your luggage, keep in mind that oftentimes, less is more. (You still have to carry all your luggage around with you on your travels, anyway.)

Remember to stick with the essentials to start. And depending on your destination, research what other essentials you may need while you’re there.

Here are a few of my packing list guides to help with your checklist:

————— Packing List Guides —————

Weekend Trip Packing List: The Ultimate Guide for any Getaway

Travel Essentials for Women: Must-Haves for Any Packing List

Ultimate Road Trip Packing List: All the Essentials You’ll Need (+ Free PDF!)

Best Camera Gear For a Travel Blogger: All My Photography Essentials

Step 10: Purchase Travel Insurance

Travel insurance may seem like something you don’t really need, but it’s always better to be safe than sorry. Travel insurance protects you from the unexpected – Things such as: if your camera gets stolen, you have a medical emergency, your flight is cancelled, or if a family member falls ill and you need to go home early.

Life happens – and life can happen anywhere, so being prepared for any worst-case scenarios by purchasing travel insurance is the best way to protect yourself financially.

Here are a few travel insurance companies that I recommend for you to browse quotes from:

SafetyWing – Offers very affordable plans for budget travelers.
Medjet – Provides additional emergency evacuation coverage, should you need help getting back home in the event of an emergency.
Insure My Trip – Great coverage for cruises and senior travelers.
Insured Nomads – Great for long-term travelers and digital nomads.

Step 11: Enjoy Your Trip!

That’s it! You’re now ready to head out on your adventure and enjoy the fruits of your labor. Be sure to remember all your important travel documents and IDs, take plenty of photos, and have fun. 🙂

I hope this guide on how to plan a trip helped you feel more prepared for your next vacation. Is there anything I missed? Share with me what you think in the comments below!