planning a getaway

Planning A Holiday: A Foolproof Guide To Easy Vacation Planning (2024)

Last Updated on March 11, 2024 by Nicole

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?

In this article, I am going to lay out how I plan and book a trip. It is very detailed. Sometimes, going into that type of detail won’t be necessary, especially if you are going to an all inclusive resort, on a cruise, or other multi-day group tour where a lot of the details are already worked out for you.

However, if you are organizing and planning a vacation on your own, then you will see below what you need to think about, and what you need to book and when, so as to make your holiday vacation planning easy and manageable.

This post may contain affiliate links. That means that I may earn a small commission, at no extra cost to you, if you buy something through my site. This helps me run my website and produce the articles that I hope you find helpful.

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

Research Is Key To Great Vacation Planning

Unfortunately, bottom line, for the best vacation, 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, and one set of transfers to and from the airport.

Other times, planning a trip 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 in Indonesia over 17 days, took 8 domestic flights, and stayed in 6 different sets of accommodation. We took tours, guided hikes, or had natural animal encounters almost everyday and saw and experienced sights that still leave me daydreaming.

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

All inclusive holidays tend to be overpriced and rarely a good deal. I discuss this in a separate article called All Inclusive Resorts: Why They Are A Rip Off!

Here is a link to my Indonesia itinerary if you are interested in seeing what our unbelievable trip looked like – A Mind Blowing 17 Day Indonesia Adventure Itinerary With Teens.

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

Should You Use A Travel Agent When 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 Trip

There is nothing wrong with using a travel agent in planning and booking your trip. 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 recommendations for you.
  3. You are not fussy. You will be happy with any holiday itinerary and hotel choices. It might not be the perfect trip, but hopefully, it will be close enough.
holiday itinerary
Photo by Willian West on Unsplash

Reasons Not To Use A Travel Agent When Booking Your Trip

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.

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-type hotels in the tourist areas.

As you can see, these small details could add up to make a huge impact on how you enjoy your vacation.

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 and booking your vacation.

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. In certain circumstances, commissions are deducted from the total cost to you, not added. 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 may have been better suited to you.

Of course, there are way more arguments for both sides. However, for me, these arguments are the most important and relevant.

holiday itinerary
Photo by Mantas Hesthaven on Unsplash

How I Use A Travel Agent or Tour Operator When Planning A Trip

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 With Trip Planning.

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 or quickest way to 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 vacation itinerary. While I work with them, I continue to research as much as I can to keep me informed about whether the recommendation is something that is really a good idea for us, 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 plan without help. (Photo by Ishan @seefromthesky on Unsplash)

Why I Do All 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

Questions That I Ask Myself When Planning

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

  1. What are the dates that I can or must travel?
  2. Are there any government advisories warning travellers against travel to the country or in any region within the country? The Canadian government sets out its’ warnings at, 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 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 for 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 travel 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 Travel Itinerary

After I research and answer those questions, I then start to get into more detail. Here are the next set of questions that I ask myself and research when planning my holiday.

  1. How should I divide up my time? If I am planning on exploring a country, I ideally 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?
  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 or too little) time in a location or whether I need to book tickets or a tour far in advance if it is popular.
  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? If I have to apply beforehand, do I have enough time to do this?
  7. Do I need any special vaccines or medication for my trip?
holiday itinerary
Photo by David Marcu on Unsplash)

Booking The Trip

Once I research and create a holiday plan, I then move to booking my holiday. What and when I book depends on importance and cost. The following is the order in which I book, the importance of each, and issues that I consider along the way.

The Two Most Important Parts Of A Holiday To Book First

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 or as soon as possible if the date of the trip is less than 6 months away.


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 can afford, or on the flight path that you would like.

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

For simple travel tips to save you money, please take a look at 10 Best Money Saving Travel Tips.


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.

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

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

  1. 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 or find something better.
  2. If for some reason the cost of the hotel room decreases (which may happen if the hotel is trying to attract new bookings), 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.

What To Book After Flights And Accommodation

Transportation Within The Country

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

Domestic Flights

How early I book domestic flights depends on two factors:

1. How many daily flights are offered, 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 later on. I like to book 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 shows that there is limited number of services offering this or 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 my International flights, accommodation and domestic flights.

planning a holiday
Photo by Sergey Pesterev on Unsplash

Daily Activities

I like to have a loose 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 half or full day tours or purchasing tickets to shows, if this what we want to do.

When I book Tours or Tickets

When I book a tour or purchase a ticket varies depending on the circumstances. 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.

However, there might be something so important to me to see or do that I book right after I buy my international and domestic flights. 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 we can’t, 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 Tours and Tickets

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.

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 really small 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. Other people want to figure everything out beforehand so very little of their holiday time is spent organizing anything.

I am a part of the second group. 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 trip itinerary planned and booked before leaving.

planning a holiday
Photo by Anders Jildén on Unsplash

Questions Left To Be Answered To Finalize Your Trip Planning

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, when you will need to book depends 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.

Last Word

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!

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

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  1. 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.

    1. 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.

  2. 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.

    1. 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.

  3. 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.

  4. 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.

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

  5. 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.

    1. 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!

  6. 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

    1. 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.

  7. 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!!

    1. 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.

  8. “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.”

    1. 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.

  9. 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)?

    1. 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.

  10. 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.

    1. 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.

  11. 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).

    1. 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.

  12. 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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