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4 Steps To Start Planning A Dream Holiday

So for the first time in a long time you are in the position to take some time off and go away. You have been dreaming of this holiday for months. Then your boss asks you when you are taking all these holiday days you have owing and you find yourself agreeing to three weeks over summer. You’re excited, you’re pumped and then you suddenly realize you have no idea where to start planning and your holiday is only two months away. Whether you are off backpacking or planning a family vacation, the steps are the same. Follow through these four steps and you will discover that the holiday of your dreams is not nearly as difficult to plan as you thought.

4 steps to start planning a dream holiday

Step one - define your dream holiday

The best place to start is to know exactly what you want. Do you like to look at the sights, take part in adventure activities or lie on the beach?

Ask yourself the following questions for you and/or your family.

What • What is your budget like? • Are you a picky eater? • What type of accommodation do you like? Are you willing to share? • Do you like the little luxuries in life? • Do you have health conditions? • Are there certain attractions you must see? • Are you a light sleeper?

• What style of travel appeals to you? • Are you an introvert or an extrovert? • Do you like being out of your comfort zone? • Do you prioritize being environmentally friendly?

Where • Is there a certain country that appeals to you? • Do you have family connections in some part of the world? • Do you have a hobby or interest that you can explore overseas? • What is the weather like on your idea of the perfect vacation? • Are you more comfortable speaking English? • Are you working on a tight budget? Travel Cost Comparison • Do you need to check travel advisory for safety concerns? When • What is the weather like at certain times of year Weather2travel • What are the peak seasons and are you prepared to pay more to enjoy the good weather? Best Time To Go • Is there a festival or event you can time your trip to coincide with? • How much time do you need to plan? • How much notice do you need to give to get time off work? • How far in advance do you need to be immunized?

This should help you define the what, when and where of your trip.

travel booking

Step two - Choose whether you want to use an agency

Travel agents have pros and cons. They will make your planning process much simpler and can provide extra support if something goes wrong. However they are seldom the most budget conscious option and if you have an unusual interest or just enjoy the freedom to plan your own thing, booking your own trip is not nearly as overwhelming as it seems.

I’m not going into huge detail about travel agents here. If you do decide to go with an agent check out my post on 34 Questions To Ask Your Travel Agent To Get The Trip Of Your Dreams.

Step three – List tasks to do

As long as you know you are not forgetting anything vital in the planning stages you can be much more relaxed and systematical in your planning. Here are some things to make sure you have covered Visas - Sometimes you need to apply for a visa months in advance of travel, other times you can purchase one on arrival. Google “getting a visa for [country name]” and you get several pages. Some will be second party agent pages but there should also be an official page for that country's immigration office or embassy. In my experience it is always cheaper to do your own visa application as opposed to going through an agent. The only exception to this would be if you don't meet the criteria and need an agent's expertise. On the web page you find, there should be a list of entry criteria that you must meet such as how far in advance you must apply for a visa, a list of things you'll need and forms to be submitted along with an address to send forms and payment to. Read all of this carefully and if you meet the criteria, there is no reason why applying for a visa need be a traumatic process. Many countries have visa waiver agreements meaning you're allowed into the country for a limited time without an official visa. Projectvisa

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Insurance - Insurance is sometimes overlooked especially by the budget conscious but trust me this is not something you want to neglect. Insurance can be intimidating but there are several great online calculators that can compare major providers. The best insurer for you will depend on your nationality and they type of holiday your planning.

Immunization - Some immunizations need to be taken months before travelling, some are as simple as taking a pill three days before you travel. Either way this is not an area that you want skimp on. You can do some basic research online but the best bet is to make an appointment with your nurse. They will know what you need and when you need to do them.

Planning – Take out a calendar and write the main attractions you want to fit in, add flights and long transits. Armed with this, you will know how many nights’ accommodation you need to plan for, how much transport that needs to be pre booked and any attractions that need to be booked beforehand. In reality you probably only need to book flights or travel between cities and accommodation. Here are some planning templates to make your life even easier.

Planning templates: Microsoft Tripit Pretraveller

Booking – Booking can be the most overwhelming part of travel planning, depending on your style of travel you may want to book transport, both international and local, accommodation and attractions. Unless you are booking an all-inclusive package you will get to choose how much you want to pre book and how much you want to pay as you go. Attractions for instance (unless you are travelling on a public holiday), often don’t need to be booked.

Here are some online comparison sites that you can use to find the best price for flights, accommodation sites tend to be more local to your destination and Airbnb is always a great option. Make sure you complete step four on budgeting before you actually finalize any bookings.

online booking

Step four - budgeting Setting a budget for your trip should be a piece of cake with all the info you have gathered. Make sure you have answered the following questions and then input the results into one of the budget calculators in the links below. What is the price range for your location? What is your overall budget? What are your priorities? Do you mind staying in a hostel if it means you can afford that once in a lifetime trek? Remember, cheap vs. quality can have a whole other meaning in some countries, so be cautious in places where safety may be a concern.

Don’t forget pre-trip expenses in your planning. You may need a pack and new gear, so make sure you add this to your budget. Save for contingencies. Most people recommend budgeting 20% more than you think you'll need. Try breaking your budget into three pieces: One- travelling. This includes flights, bus fares etc. - the things you can't avoid. Two- accommodation per night. This depends largely on the style of your travel. Three- expenses. This includes variable costs such as food, attractions and souvenirs. Remember, you won't spend the same amount every day. You might spend very little for a few days while lounging on the beach and then lots on a day of shopping. Food may also be included in the accommodation price or travel may be included in a tour, so have a look at your priorities and be realistic. You generally end up spending 1/3 more than you expected, so build in a safety net so you don't miss out on those once in a life time opportunities.

You can check out some of these great calculators’ Independent travel or Budget your trip online or simply start an Excel work sheet.

Travel Organisation

There you have it three steps to control over your unruly travel plans. Once you get the hang of it you will see that planning your holiday is not that intimidating, in fact it can even be fun. The anticipation of that well-earned holiday will help the next few months fly by and before you know it you will be reaping the rewards of your carefully organised holiday.


If you enjoyed this post check out this article on healthy travel habits or sign up here for monthly tips on saving money and travelling for longer.

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