How to Plan Your Dream Trip

I’m always surprised to see courses set up to help people travel. By all means, if you find these services useful, sign up and pay for them. I really don’t think it’s that difficult however. Here is my take on how to plan your dream trip in 9 easy steps.
1. Figure Out Where You Want to Go
If you had all the money in the world – where would you want to go?  What places have you dreamed of visiting?  What’s on your bucket list? What things have you always wanted to do? What experiences do you want to have?
Don’t think about how much it would cost you at this stage. Just list all those things you’d like to do or see, and don’t be afraid to think big.
Write it down, assume that anything is possible.  Add to your list whenever you feel inspired.  It doesn’t matter what you write down.  It doesn’t have to be exotic, or exciting, just anything that you think you would enjoy.
Your trip needs to have the power to inspire you to save and do a lot of planning.
Like Tim Ferriss basically says, a long weekend package trip to the Costa del Sol is not going to have that power.  Sailing around the Greek islands for six weeks, or a three week jaunt watching big cats in the Serengeti followed by a week relaxing on the beaches and turquoise waters of Zanzibar might.
That’s the key to it all.  Motivating your self enough to save enough money, researching where you want to go and actually booking it. Don’t waste your life wishing you could go somewhere or do something. Make it happen.
Check out TripAdvisor’s inspiration tool or the Lonely Planet site if you’re stuck.
Read the itineraries of established tour groups like Intrepid Travel and Exodus Travel for ideas. Google images, or look up where you want to go on Pinterest. Read other people’s bucket list.
If you really can’t take an extended trip and are playing with 10-25 days a year – where do you want to spend that precious amount of time?
Knowing where you want to go and being open to making it happen is crucial.  So many people I meet, go on about how “jealous” they are when they see that I’m travelling.  I really struggle with this.    Jealousy, (according to our old trusted friend Google) is “feeling or showing an envious resentment of someone or their achievements, possessions, or perceived advantages”.  It’s a negative concept that corrodes relationships. Life really is too short. If people spent half the energy they invest in feeling jealous, in pursuing their own dreams instead, they’d be a lot happier.
I often ask my friends who cry out an exasperated “I’m so jealous!”, or “I wish I could do that”, where they would like to go if they went travelling. Most of the time, they don’t even know, or are not even fussed about seeing the world in the first place.
I’ve wanted to see the world since I found an illustrated version of some Children’s World Encyclopedia. It was a book that my grandparents had bought for their children – it was old, but I was fascinated by it.  I’ve enjoyed visiting a lot of the places I read about back then, but I’ve had to sacrifice to make it happen.  Saving, not owning a house (or a deposit), car, pension, cable/Sky TV; not having an expensive wedding, manicures, meals; not buying expensive clothes, jewellery, TV, laptops, manicures etc.  I’m travelling now and have sold off most of my possessions and am technically homeless.  I’m not a millionaire, I’ve worked hard and saved a lot, and for me it’s worth it.
All of my friends are free to travel just as much, (and in many cases – a lot more, and a lot luxuriously, than I ever could), but they choose not to.  Having a house, car, certain lifestyle, nest egg is more important to them. That’s cool – please be happy with that. There is no need to be jealous of anything.  The grass is always greener people. Backpacking can be hard work. People think I spend my time relaxing on a beach sipping pina coladas all day – mainly because they spend two weeks a year doing just that whenever they go on vacation.  Sometimes I wish that’s what I was doing! But, it rarely is. It’s a lot of wandering around dusty roads; chatting to random people; figuring out how to get from one place to next lugging around a heavy rucksack; frantically trying to see far too much; lots of early mornings; little sleep and trying to avoid bed bugs in dodgy hostels.  I wouldn’t have thought that many people could resent that. But maybe they do? Anyway, I digress…
2. Prioritise 
I still have a long list of places I’d love to see, and things I’d love to do.
There are a few things that I instinctively know I want to do more than other things on the list. But, it if my gut’s a bit confused, I try to prioritise by asking myself the following questions:
  • If I only had 3-12 months to live, which of these experiences would I rather have?
  • Which of these experiences will be more difficult to achieve later in life, or would be more enjoyable at this stage in my life? For example, will it be easy or enjoyable to stay in the Four Seasons on the Maldives or backpack around South East Asia while dragging two children around with me. Or, will I really enjoy or be able to climb Mount Kilimanjaro or hike the Half Dome in Yosemite later in life when I’m 55 and my knees might be playing up?   Will I really want to camp and sleep on floors when I’m 65?
  • Conversely, what experiences would be easy or enjoyable to have with children or when I am in my 70s.
  • Which of these experiences are the most expensive?  At this stage in my life, I’m probably going to have a more disposable income than I will have at a later stage.
  • Do I want to leave for a trip at a certain time, for example in September, if so, which places are best to visit around that time?
  • Which places are changing rapidly and will be more interesting to visit now? China for example, is becoming a lot more expensive to travel around, and the rate of modernisation in Cuba for example, will probably increase dramatically over the next few years.
  • Which places are currently out of bounds? I would love to visit Syria for example but now is not the right time for me.


3. Figure Out the Best Time for Your Priorities 
When I’ve narrowed down my epic wish list to around 5-10 places/activities, I look into the best times to go visit or do what I want to do.  I use Audley Travel for this (they have a useful “When to Go” section on each of their trip pages). Alternatively, Google “best time to visit” wherever you want to go.
If you can afford the time to stay in one place for a month or two, the weather may be less of an issue than if you are going somewhere for a week.
I’m always surprised by people who spend thousands of pounds on going away only to find out that they are going in the middle of rainy season.  The generally considered “best time” to go to places might not be the warmest.  In Peru for example, peak tourist season is May to September when the days are sunny and far drier than usual, but it’s a lot colder as a result.
Be specific, rather than just researching the best time to visit a whole country.
Many countries have mico-climates, or are so big that the weather in the north of the country is drastically different to the south.  The monsoon hits various parts of India at different times of the year for example, and the weather in the north of Australia can be completely different to the weather in the south at the same time of year.
Consider whether dry sunny weather going to be important to you?  Will you be sick of the cold weather at home and desperate for some sunshine?  Will you want the weather to be hot, or would you prefer if it was cooler?  Do you really want to be in Dubai in the heat of summer, or Canada in the dead of winter, or would you prefer to visit at another time?
Do you want to see the autumn leaves of Juizhaigou or the cherry blossom in Japan? Do you want to maximise your chances of seeing a tiger? For all of these things, you will want to travel and specific times of year.
It’s not just about the weather either.  Do your research and think about your preferences and what you want to experience.
Are there any festivals you want to go to, or avoid?  If you want to learn how to ski then snowy weather might be a pre-requisite.  If you want to hike to the top of Kilimanjaro you might want to go when there is statistically less chances of bad weather.
Do you want to run with the bulls in Pamplona, or watch a sumo match in Tokyo?  These are all events that only happen at specific times of the year.
You might also have your own time constraints or want to be away at a certain time. You might have a three month gap between jobs over June to August, or want to be away for your 30th birthday in December.
There are benefits in visiting a place out of season – accommodation costs less and there are less tourists around.  Some people like this but I’m not a fan. I’ve been to places out of season and a lot of them are dead. It isn’t just about the lack of tourists. Locals often move out or go on holiday themselves during these periods.  Sure these times of year are cheaper, but that’s for a reason. Many local businesses run reduced hours or close down completely.  For example, most of the huts in Palolem in Goa are only standing for a few months a year.  Bad weather can also be more dangerous, bringing land slides, more accidents and road closures.
If you’re going to spend a lot of money to visit these places, then don’t you want to experience those places at their best, or near best at least?  Trust me, travelling in the monsoon where it rains incessantly every day is not fun.
4. Figure Out How Much Time You Need
If you need 2-3 weeks to hike the Annapurna Circuit in Nepal then that’s not going to work if you only have a week to take. If you want to travel around various countries in South America, is that really doable in just two months?
Machu Picchu, Peru
 The best resource for figuring out how long you need to experience somewhere, is communicating with people who have already been to the places you want to visit.  It will give you a chance to ask questions too – your friend might recommend a week in Paris but that’s because they’re an art gallery nut, while you might not even know what the Louvre is.
If you dont know anyone that’s been where you want to go, have a look at tour group itineraries.  It’s a good way to quickly figure out how much time you would need to travel around a country and visit places.  Factor in a day or two extra in certain places.
Downloading free Kindle samples of Lonely Planet books which usually includes their top ten picks and sometimes their own suggested itineraries can also be useful.
5. Have a Look at How Much Flights Cost is my go to resource for flight prices.  You can usually get an idea of how much things cost for the dates you might be aiming for.  I’m not a fan of booking through agents or RTW ticket’s unless there are huge cost benefits.
6. Create a Rough Itinerary/Budget
If you’re not too worried about money, then you can just look up the suggested daily budget provided by Lonely Planet in their “Money” section for various countries, and then multiply that number with the number of days that you’ll be in a country and figure it all out later.
Even then it’s a good idea to have a rough idea of where you want to go and what you want to do.  If you’re planning on sky diving in New Zealand or visiting the carnical in Rio for example, you’ll need to budget accordingly. is still my go to website when it comes to hotel bookings. I often find the cheapest prices on there, even when I visit the hotel/hostel site directly. They also have an awesome customer service team.
If you want a more exact idea of how much a trip would cost then create a rough itinerary.  You can spend weeks doing this, which is not what you want to do at this stage.  You just want a rough idea of how much a trip is going to cost you, and whether you should be looking at alternatives or not.
I usually start with a spreadsheeet with columns headed:
  • Place
  • Number of days
  • Accommodation
  • Transport
  • Activities
  • Meals
  • Miscellaneous

Place and Number of Days

The number of days figure is based on my research. Factor in time to see what you think might interest you plus the time it will take to get there and take it easy. If you’ve taken a night bus you might be very tired the next day, or if you arrive somewhere at 4pm, you’re not going to have much time to see anything.
It’s always best to go for more time than you think you will need, you need time to adjust to new places, and the additional time will give you more flexibility. You might also need to factor in time for admin and laundry and taking it easy.
You’re not booking anything yet remember – so don’t get too hung up on this number.  I find that it’s best to start with an ideal scenario and cut things out rather than add things in at a later date.
The figure in the accommodation section is easy. Type in some dates into TripAdvisor or, or HostelWorld and you’ll find out instantly. AirBnB can also be useful, especially if accommodation is expensive elsewhere or you’re after an apartment.
Make sure you check the small print for any tax that might be payable on top of the listed price. Prices stated for the US and some places in Argentina for example, don’t usually include around 16-25% tax which you will have to pay on top.
Accommodation prices vary.  Cities often cost more than towns and touristy places can also cost less than places no one ever visits. Again, don’t go over board or look up every single night, just get a rough idea of the cost.
I figure out the transport section by using Rome2Rio which can often give you an idea of how much public transport and even (petrol if you’re hiring a car) can cost.  It’s also good at helping you figure out whether a journey is doable and getting an idea of how long it might take.
If I’m in a city I might also factor in a bit for local transport.
This is usually an amount for sightseeing and any particular excursions or tours or classes I want to do like sky diving or spanish lessons. I use TripAdvisor to find companies that organise the kind of activities I want to do, or have a look at the suggested figures in the trip notes of Intrepid Travel’s tours which often list as optional activities.
For meals, in my experience it’s best to over budget.  You might have the intention of staying in your hostel and cooking for yourself most nights, or only drinking once a week, but it is difficult, especially if you like food and find out about restaurants you’d like to go to, or end up meeting and drinking with new friends, or are low on will power when it’s 40 degrees and a cold beer is calling you.
I’ve over spent on meals in the past, so I try to over budget when it comes to food and drink.  I usually use a mish mash of suggested numbers in guidebooks and the figures listed for food, water and alcohol on the Budget Your Trip site.
In the miscellaneous column I usually have 5-10 pounds or dollars per day depending on what kind of country I’m visiting.  This will cover things like laundry, postcards, phone calls to the bank, and toiletries.
Some people might want to budge for souvenirs or gifts.
After that I try and work in a 10% contingency on top.
At this stage you might be surprised that somewhere you’ve always wanted to visit is a lot more affordable than you thought it was, or you might be a bit overwhelmed with how much a trip might end up costing. Be flexible, can you cut down on expensive aspects of your trip or are they deal breakers and things you’ve always dreamt of doing?  you might not be able to visit Easter Island on your trip to Chile this time but you will be able to afford to hike around the mountains of Patagonia if you cut it out.  You might be able to go to Thailand if you don’t stay in a five star resort but is that something you really want to do, or maybe you can cut
Shwedagon Pagoda, Yangon, Burma/Myanmar
7. Check out the Visa Situation 
Don’t forget to factor in the cost of these.  Some visas can be extremely expensive, like visas for British national to visit India or Russia.  They can also take time to process, or contain restrictions.  For example, you might have to apply for some visas while you are in your home country.  Other visas are easily available from a consulate abroad, (like visas for Burma/Myanmar in Bangkok), others take weeks to get.
Once you’ve got your visa, you might have to enter your target country within a certain date which can also impact your itinerary.  We planned a huge round the world trip with China and India at the end of it only to figure out that it was going to be massively more complicated and expensive than visiting those countries at the start of our trip.
I find out what visas I need by clicking on the “entry requirements ” link on the country specific pages of the FCO website.  If you’re not British, check out your country’s equivalent.
8. Don’t Forget About Travel Insurance
This can be really cheap, or expensive, depending on your age and how long you are going for.
If you are planning on doing a few trips a year, an annual policy is often the best bet.
Make sure you are aware of restrictions, for example some providers only cover trips up to a certain length 30-90 days, and exclude snow sports or activities like sky diving or hiking at altitude.  Shop around and don’t be afraid to query any aspects of the policy if you are unsure whether it will cover you for what you want to do or not.
Best to find out now than after you’ve broken your leg in a taxi accident and you owe thousands and thousands of pounds in medical bills.
You might also want to take out separate cover for your camera or laptop.
9. Book It
When you’ve got a rough idea of how much your trip will cost and you’re confident you can pay for it, the only decision left to make is when exactly you are going to go.
Make the decision, sooner, rather than later, and book your flights.
Once your flights are booked, you can also book accommodation for your first night or two at your destination, and start thinking about what to pack.
Buy a guide book, research where you want to go in more detail.  Figure out if there is anything you need to book in advance, like tickets for certain journeys, accommodation for festival times, or even tickets for tours or museums that sell out.
If you are that way inclined, book a few places that you might want to stay.  You can often change your mind without paying anything if you use sites like to book and cancel within the cancellation period.


For all of the most important things, the timing always sucks. Waiting for a good time to quit your job? The stars will never align and the traffic lights of life will never all be green at the same time. The universe doesn’t conspire against you, but it doesn’t go out of its way to line up the pins either. Conditions are never perfect. “Someday” is a disease that will take your dreams to the grave with you. Pro and con lists are just as bad. If it’s important to you and you want to do it “eventually,” just do it and correct course along the way.” – Tim Ferriss

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