Who doesn’t love an awesome vacation? But having a great time traveling means you need to take some time to plan. Trip planning can be a daunting task for some people, but I actually really enjoy the planning portion.

6 Important Steps to Follow When Trip Planning

I’m here to explain where and how to start, how to plan efficiently, and what you can use to have a great time traveling.

The guide below does not have to happen in a linear path, and it often won’t. You might go through various steps multiple times throughout the planning process.

Step 1: Where to Go

This is probably obvious, but, hey, let’s start with the bare bones. Where do you want to go? You might already have a list of places you plan on going, so what I would suggest doing is looking up the best months to visit said destinations.

road sign pointing to different countries taken at sunset to inspire people whilst trip planning

If you have the luxury of not traveling during high seasons, I would recommend going when there are fewer tourists because you will be able to have a calmer and more authentic experience.

It is important to think about how many days you have available and how many places you want to see. Some people like to have a day or two in one city and move to another, but I like to spend a minimum of three to four days in a city before moving.

I view moving from one city to another as potentially losing a day or half a day. The more you move around, the less time you have explore.

Additionally, consider how much it will cost to get from place to place. Do you have to take a train or plane, or are you renting a car? Transportation can raise your expenses.

Step 2: Flights

Once you decide the destination(s) and the dates you can travel, you’ll want to try and find a flight for a decent price.

For this, I recommend two trip planning apps.

Hopper is useful in planning the best month(s) to go. This app will show you a calendar of the estimated flight costs, to and from your desired airports.

This is a trip planning app to search for flights. You type in the airport and dates and pick one-way or roundtrip. Momondo will create a list of flights from various airline providers, and you can organize them by the cheapest, fastest, or by what Momondo considers as the best value.

I used Momondo for my last flight coming home from Rome and found a flight for less than $400.

man at airport watching planes take off through window

Step 3: Accommodation

Typically, I use Booking.com for hotels, hostels, apartments, and B&Bs. It is a great way to peruse different options.

I find it really useful to pull up the map view and compare prices and locations. Using Booking.com will also give you slight bonuses for booking through their site multiple times, with Genius rewards. You will receive price discounts the more you use Booking.com.

Perks of Booking.com

Another reason I choose this site when trip planning, is the ability to book rooms with free cancellation and pay when you arrive. This gives me a sense of security with the freedom to change or cancel accommodations if need be.

Even if you use Booking.com, check the accommodation’s website directly to see if they have a better deal than a site like Booking. I always found it to be about the same price.

Don’t hesitate to contact the accommodation via email or phone if you have questions. Booking.com will give you the option to message the venue from their website. I’ve contacted accommodations for information about airport transfers before, or if you have allergies or are sensitive to fragrances, this could also be a reason to contact the venue to make sure they don’t use any fragranced items when cleaning the rooms.

Getting a Better Rate

One tip I have for you when you arrive at the destination is to ask for the email of a manager/owner at the accommodation. Often you will find that owners/managers will tell you to email them directly if you plan on visiting again, and they will give you a better rate through scheduling with them.

One woman that worked at the hotel we stayed at in Venice, Hotel alCodega, told us that if we came back with family and wanted multiple rooms, to email her directly for a better price. Communicating with staff is key.

Step 4: Create a Roadmap

I like to create a roadmap on paper because a roadmap will probably change as you continue researching.

A roadmap is really useful when trip planning, and can take a number of different forms. I like to create webs or mindmaps. I put the country or city in the middle and branch out from there with the tours, transportation costs, sightseeing, and potential restaurants.

roadmap of Italy drawn whilst trip planning
Italy Roadmap

Some of you might prefer making bullet lists. If you’re more creative (or bored), you could draw out a map and list the information over the places you’re going to visit.

Step 5: Tours

Tours are really useful if it is your first time visiting a city.

It’s great that there are so many different tour options because you can definitely find something in your budget — even if that budget means you need a free tour. Whatever city you are visiting, take some time to just Google “*City* free tours.”, when trip planning.

For example, before I visited Budapest, I Googled “Budapest free tours” and found a couple of free walking tours. Some free walking tours will require you to sign up online to reserve a spot, particularly in peak seasons. When you finish the tour, you have the option to tip what you think that tour was worth.

Finding Tours

Some of you may have a pretty flexible budget, so I want to give you a few options for different ways to find tours. If you’ve never visited the country before, you might just want to hop on Viator and search for different tours available in that city.

Viator takes tours from a ton of companies and puts them in one place. I use Viator to get a feel for what will be available to me in a new place. When I visited Italy for the first time, this site was extremely useful.

If you do book through Viator, you might come across a company you had a really great experience with and decide to do some more research on them. That happened to me on that first trip to Italy. I realized I was really enjoying tours I booked with City Wonders, so now I book through their website directly.

Other tour companies to consider if travelling to Europe:

  • WalkAbout
  • Rabbie’s
  • Italy on a Budget
  • Walks of Italy
  • Game of Thrones Tours
Photograph of Colosseum in Italy taken at sunset to look at when trip planning.

Step 6: Pre-Travel Inspiration and Research

Once you have a roadmap, flights booked, and accommodation ready, it is time to continue trip planning, and find some inspiration for your trip.

This may seem silly to include, but I think it is nice to remember that staying excited about your trip and slowly finding more things to see is good. Here are some ways I find excitement in those weeks before finally taking off.

  • Instagram and Pinterest

I use both Instagram and Pinterest to look up cool pictures of the places I am going to be visiting. This gives me that “wow, I am going to be there soon” feeling.

These pictures are also great inspiration for me as I dabble in photography. I start to think about how I can get a great shot like that myself. You’ll probably also find pictures people post of hidden gems or great restaurants, so these sites also become great places to accumulate some more ideas for that roadmap.

  • YouTube

YouTube is one of my favorite places to find information and inspiration for travel. There are really passionate and informative travel vloggers that will give you a ton of tips and tricks and places to add to your roadmap. I used YouTube a lot when trying to figure out public transportation and finding new restaurants. Here are some of my favorite travel YouTubers:

  • Living On A One Way
  • PsychoTraveller 
  • Daneger and Stacey 
  • Vagabrothers
  • Simon and Martina

Final Words

Well, those are my trip planning tips on how to successfully plan a great trip! These are all steps I personally take when getting ready to travel, whether I am traveling solo or with others.

If you are traveling with others, you can divide and conquer these steps and work collaboratively. Talking out the trip with others can help you recognize gaps or mistakes and help you find new ideas and opportunities.

But, don’t be afraid of planning if you are traveling solo. One of the best parts about traveling solo is being able to do what you want when you want, so you should really take your time to go through these steps.

Research places that are recommended for solo travellers. For example, in Canada, Vancouver is a great place for solo travellers. Here’s 10 unusual things to do in Vancouver.

Like this article? Here’s 8 Travel Smart Tips to Make Your Trip Less Stressful

Do you have anything specific you do when you are planning a trip? Are there any resources you used that I missed? I would love to hear about it in the comments.

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Chelsea Leigh

"My hope is to help you build a wealth of information to plan your own travel expeditions with ease. Where I’ve been: Switzerland, France, Germany, Belgium, Netherlands, England, Ireland." Check out Chelsea's latest work at her blog, Vacationer's Valley.

Author Chelsea Leigh

"My hope is to help you build a wealth of information to plan your own travel expeditions with ease. Where I’ve been: Switzerland, France, Germany, Belgium, Netherlands, England, Ireland." Check out Chelsea's latest work at her blog, Vacationer's Valley.

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