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.

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.

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.

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.

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.

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.

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.

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 https://travel.gc.ca/travelling/advisories, 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.

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?

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.

Flights

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.

Accommodation

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.

Booking.com

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

Booking.com

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.

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.

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.

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.

Everything Else Related To Booking A Trip

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.

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.

Restaurants 

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.

Nightlife 

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!

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