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Planning A Holiday: A Foolproof Guide To Easy Vacation Planning

Simple steps to create your perfect holiday.


Some people absolutely love thinking, dreaming and planning a holiday. Other people are either overwhelmed by the thought or terrified by the amount of work that normally lies ahead of them. However, everyone wants to make sure that they are getting good value for their money, regardless of their budget. Nobody wants to take a trip and then, later learn that they paid double what someone else paid for the exact same experience; or had a better hotel for the same cost; or found better flights, buses or trains that would have saved you hours of travel. So, how do you do this? How do you plan a holiday, all the while keeping your sanity, maybe even enjoying the process, and also find the best possible experiences and deals?


holiday itinerary
Where dreams take you  (Photo by Mesut Kaya on Unsplash)


Research Is The Key To Planning A Holiday


Unfortunately, bottom line, you need to get on your computer and research.

Sometimes, it doesn’t take much – perhaps, you know you want to go to Mexico to an all inclusive in February. Accordingly, many variables are known and you can narrow your search to one set of flights, one resort, one transfer from the airport to the hotel, and so on. (Although be careful… all inclusive holidays tend to be overpriced and rarely a good deal. I discuss that in a separate article called All Inclusive Resorts: Why They Are A Rip Off!)

Other times, trip planning could be a huge task. One of my multi-day multi-destination holidays, like the one we took to Indonesia for example, could take days of planning over weeks or even months. We went to 7 different destinations over 17 days, took 8 domestic flights, and stayed in 6 different sets of accommodation. We took tours, guided hikes, or had animal encounters almost everyday and saw and experienced sights that still leave me daydreaming. Here is a link to my Indonesia itinerary if you are interested in seeing what this looked like – A Mind Blowing 17 Day Indonesia Adventure Itinerary With Teens.

However, either way, it doesn’t really matter. The steps in planning your holiday are the same.


planning a holiday
Research is key in creating your perfect holiday itinerary. (Photo by Element5 Digital on Unsplash

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Should You Use A Travel Agent In Planning A Holiday?

The short answer is “rarely”. Sometimes it is better to use a travel agent when planning a holiday. However, most times, it definitely is not. Here are a few arguments for both sides.


Reasons to use a travel agent to plan your holiday itinerary

There is nothing wrong with using a travel agent in planning a holiday. In fact, there are a lot of good reasons for relying on them.

  1. You are really busy and you do not feel that you can properly plan a holiday.
  2. You are going somewhere that makes you a little uncomfortable. A travel agent may have been before or an expert in travel to that area so that they can make the right choices for you.
  3. You are not fussy. You will be happy with a holiday itinerary and hotels that might not be perfect for you but hopefully, close enough.


holiday itinerary
Photo by Willian West on Unsplash


Reasons not to use a travel agent in planning your holiday

However, most of the time, I think it is a mistake to exclusively use a travel agent to plan your holiday itinerary. Why?


A travel agent does not really “know” you when creating a holiday itinerary.

Nobody knows you and your family like you. This might sound a little corny, but the reality is only you really know what you want, like, or hope to have. You might be able to communicate some of this to a travel agent, but I guarantee that you won’t be able to communicate every detail or nuance of who you are or what you want.

Accordingly, when you use a travel agent, you are always at risk for there being something that would have been better for you had you spent the time looking yourself. Don’t kid yourself. Sometimes the difference between a good holiday and a GREAT holiday is found in the little details.

For example, you love the hotel, but wish your hotel room was on the ground floor with a patio so your kids could have easily gone out to play. You are happy you went to Paris, but you wish you had more time to shop and less time touring churches. You are happy you went to Bali, but wish that you had stayed in smaller boutique hotels off the beaten path rather than the large western hotel in a tourist area.


planning a holiday
Travelling off the beaten path away from tourists. (Photo by Jamie Fenn on Unsplash)


A travel agent may not be always thinking of you when planning a holiday.

A travel agent may not be interested in getting you exactly what you want. Let me explain. Most travel agents are paid a commission from hotels, airlines or tour operators after they book a client with them. Some hotels or tour operators pay more commission than others. This does not necessarily cost you more – commissions are normally taken from the total cost to you not in addition. However, a travel agent may book you in a particular hotel or with a certain tour company that earns them more commission than another, even when another hotel or tour operator would have been better suited to you.

Of course, there are way more arguments for both sides. However, for me, the three arguments in favour of using travel agents and the two against are the most important and relevant.


holiday itinerary
Photo by Mantas Hesthaven on Unsplash.


How I Use A Travel Agent or Tour Operator

I never ever hand over my travel plans to a travel agent for the two reasons described above. However, I may collaborate with a travel agent or a tour operator.

I love adventure travel and travel to countries that are off the beaten path. Maybe they are perceived as a little dangerous or without the comforts of home. For me, I see those same countries as having a culture untouched by tourism and most likely, with natural beauty hardly explored by others.


The challenges of travelling to remote locations when planning a holiday.

Interestingly, what inspires me to want to visit these countries also makes them more difficult destinations around which to plan a trip. Most likely, relevant information about important cultural sites or exciting adventure experiences are not fully set out online. Even if they are, it isn’t always easy to figure out logistics, like the safest way to take a family of six to see or experience them.

Accordingly, I will try and find a LOCAL travel agent or travel operator who I can COLLABORATE with in creating my holiday itinerary.  While I work with them, I still research suggestions as much as I can to continue to keep me informed about whether the suggestion is something that we wish to do, and more importantly, whether I am getting a reasonable price for booking with them.


holiday itinerary
When places are remote, they are sometimes more difficult to learn about without help. (Photo by Ishan @seefromthesky on Unsplash)


Why I do all of my holiday planning

When I travel anywhere, I want it to be “perfect”. That means that I want to:

  1. Decide on the number of days that I want stay in one place;
  2. Choose my own accommodation;
  3. Decide on what I want to do each day; and fundamentally
  4. Determine how best to spend my hard earned money.

This is how I accomplish all that.


holiday itinerary
How to create your perfect holiday. Photo by JESHOOTS


Creating A Holiday Itinerary

Getting Started on planning a holiday

The following are the most important questions that I research when I first start to plan a holiday.

  1. When can or must I travel?
  2. Are there any government advisories warning travellers against travel to the country or in any region within the country? For Canada,, but most western countries have their own.
  3. What is the weather during my proposed dates? If I plan to travel around a country, what is the weather like in different regions? Am I happy with these conditions?
  4. Which international flights should I book? This topic is further broken down into two further questions:
  • What is the cost of the international flights? Flights are a significant cost to any trip. As early as possible, I start to track the cost of the flight to understand what might be a good price or a bad price. I buy as soon as I am satisfied that I am getting a good price. If flights remain expensive, I may choose another destination or try and adjust my dates.
  • What is the best flight? For long haul destinations, a direct flight might not be possible; or I may wish to try and have a stop over on my way to explore another destination without incurring the cost of another flight. These are issues to research here.


planning a holiday
Trying to sort out international flights is super important. (Photograph by Tom Barrett courtesy of Unsplash)


Building your holiday itinerary

After I answer those questions, I then start to narrow down my research. Here are the next set of questions that I explore when planning my holiday.

  1. How should I divide up my time? Ideally, I try and stay in one place for 3 nights before I move. Based upon the total number of days I have, how many locations could I visit? Ultimately, I decide whether I want to visit multiple locations or stay in one place.
  2. Within the country, where do I want to go?
  3. In each location, what accommodation interests me?
  4. Within the country, how should I travel from location to location? What is the cost?
  5. What should I do each day? I always outline a rough plan before I finalize anything. This is very important for a couple of reasons. It helps me determine whether I have allotted enough (or too much) time in a location or whether I need to book tickets or a tour far in advance because demand may be greater than supply.
  6. Do I need a visa to enter the country? If so, do I have to apply before I arrive or can I purchase one on arrival?
holiday itinerary
Maybe you want to take long bike rides? (Photo by David Marcu on Unsplash)


Good News! For those of you excited to start planning your next holiday right away, please download your own free pdf copy of my Planning Guide with the most important steps highlighted. 

Once I research and create a plan, I then start focusing on booking my trip. What and when I book depends on importance and cost. The following is the order in which I book, the importance of each, and the issues that I consider.

The two most important things to book.

The two most important items that I book as early as possible are international flights and accommodation. I try to do this a minimum of 6 months in advance.


1. Every item that you have researched and planned is in jeopardy if you can’t get to your destination for the price that you think is reasonable, or on the flight path that you would like.

2. For many trips, this could be the most expensive item for your holiday. I like to find the best deal early and get that expense out of the way.



1. I think that having the right accommodation is super important. I don’t want to settle on a place because that is what is left. Rather, I want to choose a place because it is in an excellent location and has the amenities that are important to me.

2. Booking early usually means the rooms cost less. As hotel rooms fill up, the cost of rooms normally increase.

Related to this, if possible, I avoid advance payment on accommodation. I try to only book accommodation that I can cancel for two reasons:

A. If my plans change, I can cancel the room without penalty. Since I try to book accommodation early, it is possible that I might change my holiday itinerary.

B. If for some reason the cost of the hotel room decreases (which may happen if the hotel is trying to attract new guests), I want to be able to modify my reservation and take advantage of the lower cost (or even cancel if I have found an equally good hotel for a better price). I regularly check the cost of the hotel leading up to my trip to see if the cost has decreased.

planning a holiday
Will there be enough room for you here? (Photo by Shifaaz shamoon on Unsplash)

When I am ready to book my accommodation, I turn to to help me search for the best accommodation for prices that I can afford.


Other important items to book after flights and accommodation when planning a holiday


If I need to book flights within a country or a rental car, I also try to book these items early.



How early depends on two factors:

1. How many flights there are, the size of the planes, and the number of seats available.

2. How important that location is for my holiday.

If there is only one flight per week on a small plane and the destination is the main reason that I am going to the country, then I will likely book soon after I book my international flights. However, if there are multiple flights on large planes at reasonable costs, and I am ambivalent as to whether I go to that location, I might wait until a couple months before I book. Again, you do not want to wait too long as the cost of the flights will eventually go up as the planes fill up.

Planning a holiday
Photo by Karsten Würth on Unsplash.


Rental Cars

The cost of rental cars is also a product of demand. If you book early, you will likely get a better rate than booking last minute. However, rates can decrease if there is less demand at the car rental agency than anticipated. Accordingly, like hotel rooms, if your rental car reservation is cancellable, you can modify or cancel your reservation if you find a better deal. I like to lock in a rental car early and then, continue to check back on the cost leading up to my trip.

Private Car and Driver

Usually you are required to pay in advance for a private car and driver. Accordingly, I am cautious about booking this too early unless I am absolutely certain of my travel plans. However, if my research has shown that there is limited number of services offering this or that there is a risk of the cost increasing if I wait too long (because the less expensive services will usually be booked first), then I will book this soon after I book International flights, accommodation and other internal transportation.

planning a holiday
Photo by Sergey Pesterev on Unsplash


I like to have a plan for each day of our trip. Even if it is a “sleep in, hang by pool, and shop”, I like to take a look at the overall plan for the trip to see if we will be doing too much, too little, or too much of the same thing. I also want to give us time to rest if we had a long travel day the day before, or a late night. Once I have international flights, accommodation and internal transportation settled for our holiday itinerary, then I start booking tours or purchasing tickets to shows.

When I book.

When I book varies. Most if not all, tours and activities require immediate payment without a refund. Accordingly, I may wait a month before I start to book or even a couple of weeks, it really depends on how important one particular experience is and whether I think that the tour or activity could sell out. There might be something so important to me to see or do that I book right after I buy my plane tickets. However, that is unusual. Normally, daily tours and activities fall into two categories –

A. I really want to do “that”. So I book a month or more before we arrive; or

B. “I’d really love to do that, but if there isn’t room, I’d be happy to do something else”. So I may book that a couple of weeks to a couple of days before we arrive.

If it is high season, you need to be more alert. Some things could sell out months in advance.

holiday itinerary
Photo by Kalen Emsley on Unsplash


Where I book

One of the first sources that I review when I am trying to determine what tours or activities we might want to do in each destination is Get Your Guide. This site offers thousands of tours from all over the world. I normally book my group tours through them, but even if I ultimately decide to take a private tour with another tour operator, this site gives me an excellent overview of what each destination offers. If you have a moment, please click on the interactive link below to explore the amazing options offered.




By the time I get to this part of planning my holiday, I know that most of the work is done. Now, it is about focusing on the smaller details.

This part of creating your holiday itinerary is a lot more personal. Some people do not want everything sorted out or organized before they arrive. They are happy to do it once there. Other people want to figure everything out beforehand so very little of their holiday time is spent organizing anything.

I am apart of the second club. I want to organize as much as I can before I arrive at our holiday destination so I do not have to think or stress about the details while there. This is likely borne from travelling with 4 kids and absolutely needing to be organized. I don’t really know. However, what I do know is that I like to get as many details of my holiday itinerary nailed down before leaving.

planning a holiday
Photo by Anders Jildén on Unsplash


Questions left to be answered for those super organized folks like me!

How do I get from the airport to my accommodation?

How should I travel once I am settled in my accommodation ?

Where should I eat, have a drink, or people watch?

Where are the closest grocery stores if I plan to cook?

Am I interested in any nightlife?


Travel from airport to accommodation

If your research indicates that the best way to get from the airport to your accommodation is with Uber or Lyft, then you book once you arrive. However, if you are a family of 6 and you want to book a private van and driver, then you should likely do that a couple of weeks to a month before you arrive. If you are relying on a rental car, then you should book as early as possible for the reasons stated earlier.


Travel within the location

The same goes for travel within the location. If you are relying on public transportation or ride sharing, then nothing more needs to be done. However, if you need to book something more formal, like a private driver and car, then I would do this at least a month in advance. If you are relying on a rental car, then you should book as early as possible for the reasons that I stated earlier.



If you are keen to try certain restaurants, then you may want to make a reservation a couple of weeks (or earlier if it is a popular restaurant) in advance of arriving.



If you want to see a show or something else that requires tickets, then you will need to book depending on the popularity of that show and how important it is for you to see it. Accordingly, that could mean as soon as you book your international flights, or only a few days before.



I know that planning a holiday may seem overwhelming but if you set aside some time, research and follow my steps, you can create your own “perfect” itinerary for you and your family. Good luck and let me know how it goes!


In the mean time, Download Your Own Free Copy of Planning And Booking A Holiday.

By now, hopefully you feel that you understand the steps in planning and booking a holiday. Also, I hope that you feel that you can do it too! For those that want a handy copy of my key points by their side as they work their way through creating their first holiday itinerary, please download a free PDF copy of my Planning Guide.


If you would like to save this article for future use, please click on the photo below. 

After 45 years of travel to over 60 countries, I know a thing or two about planning and booking a trip so that I get exactly what I want for the price that I believe is reasonable. Find out how! #travel, #familytravel #traveltips, #planningaholiday, creating a holiday itinerary, holiday planning guide, holiday planning checklist, family travel tips, how to save time and money, mistakes to avoid, stress-free trip planning, perfect itinerary #gofargrowclose, easy vacation planning, foolproof guide



  • Reading this makes me realise how much planning I don’t do before booking a trip! You’ve given me some great tips, and plenty to think about before booking my next travels. I never use a travel agent but I’d think about trying it out.

    • Well by the looks of things, you do quite fine without doing a lot of planning. However, I like to have most things figured out before I travel. It makes me stress a little less.

  • These are some really important key points while planning a vacation. Research is really really important. Also, realising how important the vacation destination is depending on the flights and travel expenses. I also agree that you rarely need a travel agent, however you can collaborate with few.

    • Yes, unfortunately, in order to have a fantastic trip, you need to put in the time and do research. There really isn’t any other way to create that perfect itinerary.

  • A very handy guide to planning a vacation. Some very important points to. Because I travel so much and I am used to the flow of putting together an itinerary, when someone writes a post like this, you then realise just how much goes into planning a trip. Great that you are also offering a planning guide for download. Very handy for new travellers.

  • Very useful tips for travel planning. For me, the joy of an upcoming vacation starts the moment I start researching and planning for the trip. Planning our trips well does help make the most of the time and money during the vacation. I hadn’t known about Get Your Guide till I read your post – will check their site when we plan our next getaway.

    • I agree with you. I love the planning and research stage. It makes me dream and feel so excited about the future trip.

  • Sounds like your a seasoned travelled who has put a lot of thought into planning the perfect trip. You realise how much effort it takes to construct the perfect trip and how many steps are involved when you put it all together like this. Great tip to plan for your nightlife and book tickets in advance based on how popular the activity is likely to be.

    • Thank you Paul. For me, a lot of this is so second nature. But of course, for someone who has never done it before, it could be an overwhelming task. Hopefully this helps and inspires people!

  • Research indeed is the key but some instant travel plans are super fun. And finding the right travel agency is a little headache but i feel it is needed. especially when you wish to travel in a different country where you almost know nothing. Blogs do help but again sometimes the blogs that are on top are just there because of great SEO and doesnt actually give you important insights.
    But i did love your piece. Thanks for sharing

    • Those are all very very good points. Every now and then, I’d love to find the perfect travel plans without any effort and finding a good local travel agency in a country can be challenging. Your note about SEO is also good, however, I do think that if a blog remains at the top for a long time, it is also about quality and less about SEO. Thanks for taking the time and writing such a thoughtful comment.

  • Planning is really important if you want to make your holidays even better experience. You can enjoy your each and every moment without any tension and even you can feel more relaxed and comfortable.
    Great sharing!!

    • I completely agree. I like being this organized because then I just enjoy our holiday. Otherwise, I would be stressing about details on a day to day basis that would impact how relaxed I could feel.

  • “One of my wife’s and I’s favorite thing to do each year is to go to Western Europe either over President’s Day weekend or MLK Day weekend. It’s not a holiday over there. The weather is not as nice as it is in America, but everything is half price and you can walk straight in.”

    • That’s very smart! We always travel late March to Asia and same thing – there are practically no crowds, and there are lots of deals. The weather is usually quite nice too during that time.

  • What do you suggest for how far you should “book ahead” in terms of flights. For example, I know I’ll be in Italy and Greece the end of June- end of July. What is the timeline for booking trains, flights, and inter-country travels (including boats for greece)?

    • I would take a look at the routes that you would like to take and see what the cost would be right now. It is high season and you want to be prepared. If you are looking at flights, and there is only one airline a few times a week, then you might want to book that sooner rather than later. If there is more, you might be able to wait a couple months. However, trains, buses and ferries are different. For the Greek Islands in summer, there tends to be more options and more scheduled departures depending on where you are heading. I’d look at that too. If there is a lot, then you could likely wait until a couple months before leaving. However, again, if there is limited supply, I’d book sooner rather than later. As for cost, usually earlier booking for high demand products is better than waiting until the last minute. Have a great trip.

  • Picking a destination is immensely important, as it gives you a definite goal. It’s a lot easier to mentally get behind “I am going to Paris” than “I’m going to Europe” or “I’m going somewhere.” Not only will your trip become more concrete for you and easier to commit to, but it will make planning easier as well…because you know what to work towards.

    • That is a very good point. When I know where I am going, then I put all my energy into finding the best accommodation for us, and the most exciting tours and excursions. When it is vague, it is hard to really motivate myself to get organized.

  • Thanks for sharing this, I believe who so ever is planning a holiday need to keep in the above points in mind and with my experience in a tour with Malaysia. I will suggest you give a bit more time on choosing car rental services but in my case thanks to Goso Car Rental (Kuala Lumpur).

    • Thank you. I think that you are right. If you are going to drive, you need to pay close attention to the terms and conditions of your car rental.

  • I like how you mentioned that some people either feel overwhelmed at the thought of how much work they have to do planning vacation while others love and dream about the planning process. My wife and I are thinking of booking a room on a waterfront inn because we’re considering going on a honeymoon since we never went on one when we got married. It seems like a good idea for us to think about booking lodging at a reputable place so that we can enjoy our honeymoon as best as possible.

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