Taking a year off work to travel can be one hell of an experience.
A year of your life to do with as you please and see the places you’ve always dreamed of with the thought of coming home so far away that it feels like you’re travelling forever.
The Positives and the Negatives
In this post though, I talk not just about the good sides of taking a year off work to travel, but also the potential impact it can have on your career and bank balance.
We also run through some case studies of people who’ve been there, done it and inevitably got the t-shirt (or some ill-fitting elephant pants!).
Helping you to Make up your own Mind
This post aims to make the whole process of taking a year of work that easier. Each section contains detailed information so you can easily make decisions about your future plans.
So let’s get this show on the road!
- Should I Take A Year Off Work?
- The Case For Taking A Year Off Work To Travel
- The Case Against It
- Alternatives to Taking A Year Off
- Minimizing the Impact of a Year off on Your Career
- How Much Does Travelling For A Year Cost?
- Things to Do in a Year Off
- Planning a Year off Work
- Returning To Work After A Year Off
- Examples of People Who’ve Taken a Year off Work to Travel
- Signing Off
Should I Take A Year Off Work?
👿 Yes, yes you should 😇
😇 No, no you shouldn’t 👿
Which one is the angel and which one the devil in this situation?
The one telling you to take a year off or the one that isn’t?
Well, that depends entirely on your personal circumstances.
Unfortunately, this post won’t answer the question for you but, by the end, you will have the information you need to make up your own mind.
What I do offer is honest cases both for and against taking a year off work to travel and practical advice that will help you plan if you decide to do so.
The Case For Taking A Year Off Work To Travel
Taking a year off all boils down to your risk tolerance.
It’s similar logic to investing.
When you’re young the advice is often to invest heavily as you have more time to make up for it later in life if you do lose some money early on.
This argument could also be used when we discuss taking a year off to travel.
Ageing is a guarantee and time passes on us all without discrimination. As you get older it becomes more difficult to find time to travel. Kids arrive, money is needed for pension pots and you end up in more senior positions in the workplace, which have more stigma attached to leaving them and walking away.
Of course, none of these obstacles are insurmountable, but the point I’m making is the longer that you leave it the (potentially) harder it becomes.
Time to make an investment in your life that will create stories you’ll be telling for years.
When you take a year off to travel, almost every day will hold a new experience, you’ll make more memories in one year than you likely would in ten years of normal routine.
This isn’t as measurable as earning more money or being promoted but when you look back on your life in 60 years time you are more likely to remember the big adventures than the countless hours spent investing your time making money for someone else.
On a year-long trip, you’ll take risks, meet people, see the world, and grow in a direction you would never have imagined.
That growth will help to shape you as a person, continue when you’re back from travels and affect every decision you make the rest of your life.
In short, the potential payout is massive and something no amount of money can ever buy.
And there’s also an insurance policy….
You can also always cut your trip short if you don’t love it or double down and come home when you feel it’s time.
Therefore at least some of the risk is controllable and mitigable.
But won’t taking a year off put me behind at work and mean I need to catch up?
This question always puzzles me.
Catch up to what?
This seems to me that life is treated as one big rat race, in which you’re competing with everyone else and that your only aim is to do better than your peers… like one big zero-sum game.
That seems pretty fucked up.
Even if it is true that you could never ‘catch up’, what about the life enjoyment you have gained that others may not have had?
Isn’t enjoying your life the ultimate goal, not earning more money, a bigger house or more stuff?
I don’t get it.
Aren’t you, in a sense, AHEAD of others who have only been slaving away at their job?
Life is not a race.
Life is not about comparing yourself to other people.
Life is about taking your own path, enjoying what you enjoy and trying not to worry about what everyone is doing.
It’s not easy, but here I rest the case for taking a year off.
And in summary, you only live once.
The Case Against It
I promised that in this article I’d also play the devil’s advocate.
So here’s some advice to the contrary.
You don’t NEED to take a year off work.
Here are a few things to think over before you book a flight:
Why do you want to travel?
There is no doubt that travel is exciting, but too many people taking long-term breaks because they are not happy with their current lives and set out to find some kind of solution to their problems.
Is that the case for you?
Sometimes travelling solves your problems, but usually only for those who are already reflective, self-critical and willing to grow. If you don’t tick these boxes already, travelling only postpones the question, it does not answer it.
It becomes travelling for the sake of travelling.
I want to see the world, meet different people and experience new things
You don’t need to travel to another country to do this!
When was the last time you were a tourist in your own country or city?
When did you try something new or different?
Trust me, if you are in a city, there are tonnes to explore and find out.
Travelling overseas after exploring your own place is that much more fruitful. Why? Because you have widened your own local knowledge and perspective and have your finger on the pulse of the area which will give you more to compare your travels too.
It’s going to set you back financially
A year off to travel is expensive.
Let’s say you save 20% of your income for five years to give you enough money to take a year off.
That could have been enough money to allow you to retire 10-20 years earlier (with the effects of long-term compound interest).
It isn’t a deal-breaker but you also need to be very careful not to damage your future.
You’re going to need upwards of $15,000 to make this dream happen.
That’s a deposit on a house.
That’s £15,000 that if put into a compounding ETF growing at 5% for 30 years would we worth $67,016.16.
This is a huge decision to take financially, one that we discuss further on in the post and one that shouldn’t be taken lightly.
You’re going to lose traction in your career
Yes the impact can be mitigated (more on that later) but there is simply no way taking a year out won’t impact your career in some way.
Now, that might be an impact for the better but, in the more competitive workplaces in the world (I’m looking at you USA), taking time out to ‘follow your dreams’ is not exactly encouraged.
You’ll likely see people with lower capability get ahead of you while you’re away, your benefits will almost certainly be frozen and you’ll see key sponsors move on to different companies.
And there’s also the very real chance that you won’t find work when you return. Who would you manage if your year off becomes 18 months or two years? Later on, we discuss building a plan to return before you leave to try and make sure this doesn’t happen, but there is a very real chance there may not be a role for you when you get back.
None of this may matter for you.
Your career may be the very reason you want to take a year off.
But do not under-estimate the long-term impact it could have.
Alternatives to Taking A Year Off
Take a Shorter Sabbatical
Use up Annual Leave
Some people find long-term travel is just not for them.
I love travelling, but outside my longer sabbaticals, I have still found lots of time to travel in my life.
On shorter trips, I can pack light, don’t have to worry about big things such as renting out the house or what to do with the cat (thanks neighbours) and get to see sights and experiences in bitesize chunks.
For me, it’s great to be able to take multiple trips throughout the year: some 2-3 week long, some mini-breaks or long weekends.
I know it’s European privilege of having enough holiday days and a good selection of places to travel to close by, but this is the way Becca and I have managed to visit over 80% of the countries we’ve seen already.
Find a Job Where You Can Work Remotely
Another option is to become a remote worker.
For a recurring monthly cost of $2,000, the Remote Year will arrange for you to work in a different place in the world every month, provide a co-working space, somewhere to live and even help make arrangements to link up with your employer.
Minimizing the Impact of a Year off on Your Career
It would be unrealistic to suggest that taking a year off of work won’t have any impact on your career. In the worst-case scenario, you’ll miss out on key training, be passed over for promotions and lose your network. You may also struggle to find work when you return.
If you’re strategic about it though, taking a year off work to travel doesn’t have to have a huge impact and you can mitigate some of the biggest risks.
Take the time to consider where your career might be in a year’s time. Will you be in more or less the same situation or are you pushing for bigger things? For most of us, the chances are we’ll be in the same place doing the same thing in a year’s time.
Careers have changed in the past couple of decades. The days of a ‘job for life’ seem well behind us, with most people opting for jobs in 5 to 10-year sprints. Self-determination and regularly switching jobs has minimised the impact of taking time off, as you can transfer those skill into other workplaces.
You can always get a similar job when you return, be a year older in a job with the same title, and recoup the money spent travelling but you can never have the same birthday twice.
Here are my top tips:
- Have a clear plan for what you want to do when you return
- Don’t burn bridges on your way out
- Remember why you want to do this in the first place
Have a Clear Plan for Your Return
Firstly, you’ll need to ensure you have a clear plan for what you are going to do when you get back. If you’ve managed to agree on a sabbatical with work then great, you’ll be coming back into a workplace you know on your return.
If not it can really help to have an idea of what you want to do and start to make those connections before you leave.
Ensure your LinkedIn profile is up to date, change your status to ‘open to opportunities’ and make connections with recruitment consultants in your field. This should mean job opportunities start to come your way whilst you are travelling so there is not a gap when you return. It’s easy to conduct interview whilst travelling, I got a job in Australia via a Skype interview from a hotel in Vientiane, Laos!
Just make sure you aren’t coming home with no plan and no idea for how to get your feet back under you. Find out what you’ll need on your resume in order to obtain the job you want when you’re back and take initial steps to gain those skills and experiences.
I like to recommend looking up people on LinkedIn who have the type of job they want, then reverse-engineer their career moves to figure out what you need to do next. I’m not saying you should reach out to them – just study the moves of a few folks who are in careers you aspire to and take some small steps to strengthen your own experience and strengths so that you can get a job like theirs (or a step closer to theirs) in the future.
Don’t Burn Bridges on Your Way Out
If you’ve managed to get your year signed off as an extended sabbatical then remember your boss has been good to you. There are no laws guaranteeing sabbaticals in the way there are for annual leave, sick pay or maternity leave.
Be courteous and respectful in the weeks counting down to when you leave and,if anything, ramp up the pace to say thank you for signing off your break.
If you’ve decided to quit your job then the same rules apply. Industries are remarkably small as you move up the hierarchy, so the chances of coming across the same people later in your career are high.
Treat them well, be grateful for the opportunity you’ve been given and show respect – you never know when you’ll need their help again in the future.
Remember Why You Want to Do This in the First Place
This play (say it quietly) isn’t about your career.
In fact, your life isn’t about your career.
You want to take a year off to travel for other reasons: to experience, to learn, to grow.
You can pick up your career when you get back.
Yes, you may lose a year of experience, see some colleagues who are less able than you get promoted and find that your sponsors have moved on.
But that’s life…
…you only get one go at it and if your main calling is a career then go you.
For me, life is about balance.
Yes, I want success in the workplace, but not at the cost of everything else.
I want to spend time with my family, see as much of the world as I can and have endless stories with which to bore my Grandkids!
That’s why I’m here.
And that’s why you are reading this article.
Don’t forget it as you move through this process, or it’s easy to get consumed by everyone else’s view about what YOUR career and more importantly, YOUR LIFE should be.
How Much Does Travelling For A Year Cost?
The shortest and most accurate answer is ‘it depends’.
But you can make it work for somewhere between $15,000 and £25,000 a person.
Some parts of the world are going to be much more expensive than others.
It’s possible to travel in Southeast Asia from around $750 a month but you’re likely to quadruple that figure travelling in Western Europe, Australia or North America
$50 a day would be $18,600 for the year and seasoned traveller Nomadic Matt spells out exactly how to do so in his bestselling book:
What usually makes travel more expensive is a lack of time. Planes generally cost more than boats, trains cost more than buses.
The great thing about having a year off to travel is that time is less of a pressure than normal. You can take the long way, or just stay in one place for a while and house-sit in free accommodation.
You can also mitigate some of the cost by earning money as you go [see 9 Ways to Make Money While Travelling].
The Cost of Not Working
You also need to consider the cost of not working.
It isn’t as simple as removing your salary from the calculation, you also need to consider any future losses.
For example, if your pension contribution is worth £500 a month and will get you a 5% return across its lifetime, missing a year’s worth of contribution could cost you £20,318.13 if you were 25 years from retiring (and this doesn’t even include your employer’s contribution)
If you’ve quit, there also may be future loss of earnings to contend with. If the jobs market has dried up whilst you are away, you might have to take a job at a lower level when you return
Obviously, don’t blow all your savings on this, you should have enough to live on if a job search take longer than you thought when you return.
USEFUL FINANCIAL RESOURCES:
– Can You Afford to Take a Sabbatical? [Complete Guide]
– Financing a Sabbatical – Complete Resource Guide
– How I Travelled the World on $19,640.73
– How Much Does it Cost to Travel the World for a Year?
– The Budget for a Year-Long Round the World Trip
Things to Do in a Year Off
You know that trip you’ve always wanted to make but have never been able to find the time?
This is your chance…
- Drive Route 66
- Backpack Australia, New Zealand and Fiji
- Overland the Silk Road
- Horse ride through the Patagonian Andes
- Cycle from Cairo to Cape Town
- Learn Shaolin Kung Fu
- Do the Mongol Rally
- Circumnavigate the globe in a yacht
- Take part in a conservation project
- Follow the Gringo Trail
…there are no boundaries, no limits just go and make some memories!
USEFUL FURTHER READING:
– 30 Life-Changing Career Break Ideas
Planning a Year off Work
Do not under-estimate how much planning is involved with taking a year off work.
Planning a route and tieing up loose ends may be easy for some
How to Plan a Route for Long Term Travel
Planning to travel for a year off will probably be very different from any type of travel planning you’ve done in the past.
You may be tempted to lock down as many details of your itinerary as possible however the experience of people who’ve been there before would suggest the best idea is to plan out a broad route and then go where your heart takes you.
My advice would be to plan in an outline, maybe a month-by-month wish list and then book a plane ticket to your first country. From there you can assess how you much you’re enjoying each place and whether or not you want to extend or cut short your time there.
Remember, the more you move around (especially flying) the faster your costs will go up.
Try and spend more time in fewer places, see as many small towns as big cities, and experience countries the way local would. Use the restaurants packed full of local people rather than tourists and use your biggest commodity (time) to get away from the usual tourist trail.
I would definitely have some goals to guide you – Cities you must visit, festivals you want to be at, people you want to meet. This will give you structure and mean you’re not just wandering around aimlessly.
But outside of that just go slow, keep your eyes open and enjoy the world around you. You will be one of the lucky few who’ve had this much time to experience it.
FURTHER READING: Sabbatical Planning Guides
Sorting out Your Life Before You Leave
You will find that there is a massive amount to be done before you pack up and leave for a year. Sorting out your house, pets, cars organising insurance and even registering to proxy vote it is an intimidating list.
Below are a few highlights from the list Becca and I put together before we took our last sabbatical, though if you want the full list then visit the link below.
FURTHER READING: 35 Things To Do Before Long-Term Travel [Checklist]
- Book your initial flights (or a round-the-world ticket)
- If you own your own home decide if you’re going to rent it out for the time you’re away. Be away your insurance can be invalidated if it’s empty for more than a certain time
- Check that your passport will be in date for the duration of your year off (some visas require it to be in date for 6 months after leaving)
- Organise someone to look after pets
- Build a list of the essential gear you’ll need to buy before leaving (our example list is here)
- Make sure you’ve got travel insurance. Don’t get caught short here (link to my favourite provider is at the bottom of this post)
- Check credit/debit cards will be in date for the year, if not re-order
- Order a low exchange rate credit card
- Check if you need vaccinations for the countries you’re visiting and book in
- Check visa requirements for the countries you’re planning to visit
- Register for proxy voting if you’re going to miss a key election
- Unlock your phone so you can buy foreign SIM cards
- Pay for mail forwarding for your home address to a trusted person or use a service who will scan it in and email it to you
- Order additional medical prescriptions
- Apply for an International Driver’s Permit (if needed)
- Photocopy key documents (passport, travel insurance, driving license etc) and upload a copy to a Dropbox file
- Put your email on out-of-office and set up a voicemail on your phone
These are just a few suggestions, there is a full 12-week plan on the link above.
The key is to record everything as you think of it and then plan in some time once a week to review the ‘to-do’ list and make sure it’s dropped into your calendar with a date on it. Whilst the list may be huge, when it’s broken down into smaller chunks it is much easier to deal with.
Returning To Work After A Year Off
How to Explain Taking a Year off Work on Your CV
Spending a year to travel the world is something most people dream about and most will completely understand your desire for doing so.
Employers are becoming more understanding of these kinds of career gaps. It’s more common than ever for people to take time off to travel, raise children, learn new skills and various other reasons.
Most recruiters are far more concerned about employment gaps that don’t appear to have been planned or utilised.
We’re talking things such as:
- Being fired
- Being made redundant and then not having the skills, interview technique or desire to find another role
- Quitting one job but then not actively seeking another (shows you may be a flight risk in future)
Be prepared to answer questions about the year off when you do start looking for jobs again.
Have an explanation ready for when you’re in job interviews. Make it clear that your year off was a personal choice, how it enriched your life, and make it clear you’re ready to commit to a new role. It’s also a good idea to keep your toe in the water during the year off and make sure you stay up to date on skills and technologies in your field. The biggest concern employers will have about your gap year is that you’ve lost touch with your field and your skills have fallen behind. If you can offset that fear, then it’s hard for them to say no.
Taking a year off to travel can make an amazing discussion point and most interviewers will love to hear your stories, and if anything will be a little jealous.
You just have to make sure you frame it correctly.
Just own it confidently:
- You chose to leave, not because you couldn’t find work
- You went to these places because you wanted to be immersed in new cultures and challenge yourself
- You learned all the great life lessons that you will be applying to your life going forward
Travel teaches a whole different set of skills which can be valuable to a company.
I would also suggest framing the experience as if it was a stage in your life and now you’re ready to knuckle down. Even is this isn’t entirely the truth, how many people are completely truthful at an interview?!
Go with something like:
“Visiting these places had been a dream of mine for a very long and I learnt lots along the way. Now with that done, I am looking for a stable job doing something I think I would love doing.”
It might sound a little cheesy but it will work!
Examples of People Who’ve Taken a Year off Work to Travel
A 31-year-old actuarial takes a year off and visits six continents
Lisa is also known as TheHotFlashPacker, here is her story….
At age 31, I decided to take a trip of indeterminate time.
I had reached the highest Actuarial professional designation a couple of years earlier but my career seemed to be at a standstill. I also had no children, husband, or prospects, so I quit my job as an insurance Pricing Actuary and sold my house and car and bought a backpack! I travelled for 13 months straight and took me to six continents visiting:
- Eastern and Southern Africa
- The Andes countries of Ecuador, Peru, and Bolivia
- Easter Island
- New Zealand
- A few countries of Southeast Asia – Singapore, Malaysia, and Thailand.
I returned to the USA for a wedding and decided to do a trip along the Lewis and Clark trail for the 200th anniversary. At that point, I wasn’t ready to go back to work so I went back to Ecuador to teach English for the next seven months.
While the trip was nearly 15 years ago, my budget was quite low – I recall each day in Africa averaged $70 per day and each day in South America averaged $25 per day (with the exception of my trip to the Galapagos). For my trip, the airfares were the biggest budget buster, with over $5,000 spent on flights.
If I could do it again, I would probably travel around at a slower pace and do less flying. After nearly 20 months on the road, I returned to the USA. It was a couple of years before the recession so I was able to get a few job offers within a month of returning to the states. Finally, in 2019 I stepped foot on my 7th continent, a dream since achieving my 6th continent on my sabbatical.
An IT consultant visits 35 countries in 352 days
Lena runs the travel blog NagoyaFoodie.com….
After living and working as an IT consultant in Tokyo for about three years I had enough. Enough of the repetitiveness of one day followed by the next, getting up, going to work, going home, watching a bit of TV, going to sleep. Five days of the week. Weekends were nice but I didn’t like Tokyo that much, with all the high-rise buildings, crowded trains, and hectic.
It was time for a change and, having saved enough for a year off, my and I boyfriend quit our jobs in June 2018 to go on a trip around the world.
We gave up our tiny apartment in Tokyo, packed everything we couldn’t sell or give away into boxes and said goodbye to friends and family.
With just a backpack we set out to explore the world in high-speed. We knew we had a one-year limit which led us to travel quite quickly from city to city and country to country. In all, we visited 35 countries in 352 days. With two stops in between in Japan and Germany (to see our families and to recover a little bit).
We roughly spent three months in Africa, Asia, and South America with the rest of the time in the US and Europe. We didn’t really follow a fixed route, planning only a little bit ahead and chasing the warm climate all around the globe.
It’s really hard to say which place I enjoyed most, but I am really looking forward to exploring more of South America, and I can never get enough of Asia!
During the trip, we often joined free walking tours, as a way of getting to know new cities on a budget, and whenever possible we would also join food tours. I felt that through the food I could learn a lot about the culture of a place, and trying local dishes was always a highlight for me. In all, we spent about $50,000USD for two. I wouldn’t say that is a lot, but there are definitely people out there who have spent considerably less.
That is why I decided to build my own food tour business upon my return to Japan. During my trip, it became clear to me that I didn’t want to work a corporate job anymore and that I really wanted to be my own boss. Having freedom just tops my list of priorities.
So, I started working on my dream while I was still travelling. Setting up a website, creating a simple business plan and starting research. We returned to Japan at the end of July 2019 and I could finally really get started. It took until October to get my work permit and to register as self-employed, and by then I had my first food tour ready and 4 bookings for the first month. You can find my food tours on NagoyaFoodie.com.
My trip around the world helped me sort out my priorities in life, and it was an incredible experience. But it was also really challenging at times and I am happy to be back in Japan, where I get to sleep in my own comfortable bed every night. I learned a lot while travelling the world, and I think my experiences will help me grow as a person and professionally. I really encourage everyone to travel the world!
A couple visit 11 countries for €13,000 per person
Lotte runs the Phenomenal Globe travel blog….
Taking a year off to travel was an amazing experience. During this year, there were so many highlights…
But if I have to choose:
- Off-roading and camping in Oman were very special.
- Hiking the Everest Base Camp trail was the toughest but also the most rewarding thing I ever did (except for giving birth to my son😉).
- The ultimate freedom of living out of a van in Canada and the USA for almost 5 months, visiting National Park after National Park is something I’ll cherish for the rest of my life.
There was much more, but for me, these were the experiences that stood out the most.
Before leaving home, I was working as a Lean Six Sigma Consultant at a Dutch Bank. I worked 36 hours a week (which is considered fulltime at most companies in the Netherlands, lucky us) and very much enjoyed my job. However, after a five-month sabbatical, my desire to explore the world had only become stronger, which is why my husband and I both quit our jobs to travel until the money ran out or we decided we had seen enough. We felt it was a perfect time, as we could easily sublet our apartment in Utrecht, didn’t have any kids at the time and had saved the necessary funds.
After one year we returned home and I quickly got a new job (at the same company) as Team Manager of the Investments department. My husband also found a job within two months as a Software Engineer. We’ve both been working at these respective jobs since, but I’m sure we will take another sabbatical in the future…
Of course, a year of travel isn’t free. We saved up a lot of money and ultimately spend around €26,000 (for us as a couple, so €13,000 per person), which comes down to just over €2,000 a month. I don’t know about you, but that’s actually less than I spend during a month at home…
Overview of our route:
- Dubai 4 days
- Sri Lanka 1 month
- Oman 3 weeks
- Nepal 1 month
- Malaysia 2 weeks
- Taiwan 1 month
- Canada 2.5 months
- USA 2 months
- Indonesia 2 weeks
- Australia 6 weeks
- Iceland 2 weeks
A ladder-climber gives up her city job to travel through remote parts of the world
Jacs documents her family travels at FlashpackingFamily.com
Have you ever had that feeling that there’s more to life than a 9-5 routine? Have you sat at your desk dreaming of quitting your job and seeing the world? Do it!
I spent years climbing the corporate ladder in a major bank but there was a niggle that I was missing out on life. My salary and bonus increased each year, but it didn’t bring me joy, so after 10 years I quit to take a year out travelling with my partner.
I was in my mid-thirties and it was a now or never moment. We wanted to travel before having kids because everyone knows you can’t travel with kids, right?
We packed a tent and set off for four months in Africa, travelling by public transport. After Africa, it was Sri Lanka for a month and India for three months. After India was Nepal for some trekking before driving to Lhasa in Tibet. From Tibet, we travelled to China and down through south-east Asia for four months.
My highlights were:
- Seeing gorillas in Rwanda
- A music festival in Malawi
- Many African safaris
- Seeing tigers in India
- The Dalai Lama in Dharamsala
- The Potala Palace in Tibet
- A balloon ride over the Amer Fort in Jaipur
- The orangutans in Sumatra
Having worked for 15 years, we had decent savings and saw this as a once in a lifetime opportunity. While there were lots of £5 hostels, we also splurged in places. We spent £14,000 each for the 12 months.
On return, we both went back into similar lines of work. As for travel after kids, well, we discovered that you can actually travel with kids and set up Flashpacking Family – a Family Travel Blog to document our adventures with young kids in the hope of inspiring others to do the same.
I hope you’ve enjoyed this comprehensive guide on taking a year off work to travel.
In summary, make informed choices, be brave and plan well.
There is information right the way across this site that will help you to do exactly that.
If you do decide to take the plunge, let me know in the comments below as I’d love to hear your story (as would others!).
Good luck and happy travels,
Useful Tools for Booking Your Sabbatical
I always use Skyscanner or Agoda alongside Google Flights to make sure I’ve got the best price. I use Google Flights to save a route and monitor price changes and a combination of Skyscanner and Agoda to get the cheapest tickets.
If you are in the UK I would also highly recommend signing up for Jack’s Flight Club to get incredible flight deals sent to your email inbox every week.
When booking accommodation I always start with Booking.com as they generally have the best range and prices. I also regularly use Airbnb for longer stays and apartments in cities (use this link for £25 off your first stay). For a different experience try signing up to Housecarers for free house-sitting opportunities (get 10% off membership with this link).
Travel insurance might seem like an unnecessary cost, but when a flight gets cancelled, injury occurs or you damage a piece of gear you’ll regret not paying in advance. I’ve used World Nomads for two sabbaticals and (after badly damaging a hire car in Laos!) found the claim process to be simple and transparent.
Getting from the airport to your destinations is an added stress after a tiring flight, so take the guesswork out and pre-book with JayRide.com. Their prices often beat the local taxis and I've found them to be reliable and easy to use.