15 tips for how to plan an overseas holiday

How to plan an overseas holiday so that every day is awesome

Nikki ParkinsonTravel 34 Comments

The holiday that now seems like a memory has me scrolling back through the photos on my phone just to double check that it really did happen.


I mean, look at this …

10 things to do on the Croatian Island of Vis | Stiniva Beach

{Want to play catch up? Here’s what I recommend to do and where to stay in Rome, the Amalfi Coast, Split (Croatia) and the Island of Vis (Croatia)}

While we were away and since we’ve arrived home, lots of people have asked me for tips on how to plan an overseas holiday. I’m far from an expert here, I’m not a travel agent and, up until five years ago, it had been a long time between trips overseas.

What I am is a planner. I look at that super-precious annual leave away from my business and become determined to make the most of it.

The 15 tips below are things that I’ve either picked up along the way or I’ve used on this trip – or previous overseas trips – and they’ve helped make a difference to our time on the ground.

The way I see it, every day needs to count – especially when you are travelling half way around the world. You won’t be able to control everything that happens each day, but with a little pre-planning you’ll create good memories that will carry with you long after the jet lag has subsided.

15 tips for how to plan an overseas holiday

15 tips for how to plan an overseas holiday

1. Work out a budget. This is a biggie, yes? This will not only frame where you can plan to travel but also how long you’ll be away and how you want to spend your days at your destination. What can work in your travel budgeting and savings favour is that you can spread out the expenditure if planning in advance. You can book your airfares on the “earlybird” deals that typically get rolled out in September/October each year for travel in the following year. This means you can not only possibly secure a better price but you’ll split up the payments for the holiday. You’ll have to pay for your flights when you book but can then hold off booking accommodation until later. Talk to your travel agent so they can let you know when the deals are published – or sign up to your preferred airline’s email list.

2. Book annual leave. I run my own business and there are two times during the year when it is quieter than others (mid-year and end of year). If I don’t take time off at those times, I don’t get a holiday. This was a tough lesson to learn in the early days of Styling You. Mr SY has four weeks’ annual leave and our youngest is at a school where taking time out of the school term is frowned upon (he also doesn’t want to miss any days of his own volition), so we have to work within limited times and within school holidays. This means booking holidays in advance to secure annual leave and checking the school holiday calendar in advance. Our son gets almost three weeks in the middle of the year, so it’s ideal for a northern hemisphere summer break.

15 tips for how to plan an overseas holiday

3. Decide on a destination. This is tied in with the budget and when you can book your annual leave but it also comes down to what you prefer doing when on holidays. If it’s warm we like there to be beaches for at least some of our trip. Then it came down to a matter of deciding which country’s beaches. On this particular trip, we wanted to visit another part of Italy after falling in love with the country and the Puglia region two years ago.

Mr SY and I had our first holiday together on Santorini 15 years ago, so we also toyed with the idea of going back there … until I checked out the peak-season accommodation costs on offer. For similar accommodation/views/pool in Croatia, we paid about a quarter of the price. We’ll go back to Greece once school is done and we can travel early September. Croatia came up for us as a consideration because two families, who we are friends with (and have travelled with), have been there in recent years and raved about it. We trusted their raving and have now joined them in their collective love for this country.

Once I’ve decided on the destination country, I go down the rabbit hole that is Google and Instagram, looking for recommended places to stay in those countries. I look to blogs over the bigger travel sites. TripAdvisor can be great but I also find that it can be more critical than constructive. I look at it but don’t take all the travellers’ comments as gospel.

10 things to do and see on the stunning Croatian Island of Vis

I found the island of Vis by starting with a map and searching for “islands in Croatia”. This island repeatedly came up as the “prettiest” and the quietest – hugely appealing for a planned week of relaxation in one spot. It was after deciding on Vis that we discovered our good friends had stayed there for a month two years ago. That confirmed we were on the right track.

9 things you can’t miss on a short stay on Italy’s Amalfi Coast | Positano

When I started searching about places to stay on the Amalfi Coast, Praiano came up time and again because it was close to Positano (you can even see it from Praiano) but quieter and less touristy that its flashy big sister. That was exactly what we found and fell in love with. In a nutshell, talk to your friends, stalk Instagram and devote quality time to Google. A good travel agent is also gold in helping you decide a destination based on the time of year you want to travel and your budget.

4. Book long-haul flights. I’ve mentioned this above but this is crucial to the planning process because until you have these in place, you can’t book anything else. If travelling at peak or popular times of the year, the earlier you book everything the more choices you’ll have. What we do and I suggest you do this too, particularly if one member of your family travels a lot for work, is stick to one airline loyalty program and have points pooled to that person who does the most travel. We do this and it means that I’m usually travelling at Gold or Platinum status and we can then all access priority boarding, seating and airline lounges while travelling. Mostly, I can take one guest in with me and on our last trip we were able to pay for our son to access the lounge. This very much helps if you have a layover during a long-haul trip. You can refresh a little, there may be showers and you can recharge in relative peace. Check your loyalty program’s conditions and also what any codeshare arrangements there might be when booking international flights with a partner airline. 

15 tips for how to plan an overseas holiday

5. Take out travel insurance. I’ve talked about this a lot – it’s as essential as your passport. I take mine out when I book our flights. A lot can happen between booking those flights and taking off for your holiday. See below for my travel insurance of choice.

6. Determine what you can realistically see in the time you have on the ground at your destination. We are more the type of travellers who like to immerse themselves a bit and not feel that we’ve got to tick off a hundred things in a country or continent – just because we are there. That annual leave is precious and we need to build in relaxation time to re-charge. You may be different and that’s very OK. You need to build an itinerary that fits in with your travel personality.

10 things to do and see on the stunning Croatian Island of Vis

I’ll map out our full days and nights in each destination. The advantage of northern hemisphere summer travel is that it’s light until 9-10pm. We find that gives us permission to siesta (it’s so hot from early afternoon anyway) and then come out early evening again. Breaking down each day like this gives chunks of time to which you can allocate a beach morning, a tour, a restaurant booking etc.

I don’t fill each and every chunk of time before arriving at our destination but once there we sit down together and work out how we can best make the most of our location. Being there and getting your bearings helps to be realistic about distances and local transport too.

7. Work out how you are going to get from city to city or country to country. This can be some of the trickier things to work out. I found the Rome2rio website and app invaluable for getting my head around this. You just put in your departure point and arrival destination and the app brings up all the available options from car, to train and plane (or combinations of all three). I used it even before booking our long-haul flights as I was able to work out that Rome would the best Italian city to land in from Australia and for jumping over to Split. I love how the app gave approximate times and prices for the travel too as that helped me to decided whether we’d be better off booking private drivers for different transfers and tours. In many cases it was just as expensive for three people to catch a combo of trains and buses as it was to book a driver to take us from door to door. I found out how to book the ferries between Split and the Island of Vis via an online search. My travel agent booked our Rome to Split flights.

10 things to do on the Croatian Island of Vis

8. Research and book accommodation. At the core of our holiday was a week spent on the Island of Vis so this was the first thing we booked and secured after booking our flights. Then about about five months before travelling, I spent a day searching online for accommodation for the Amalfi Coast, Split and Rome.

10 things to do on the Croatian Island of Vis | Villa Linne

We were travelling at a peak time for Europe, so knew not to leave this until the last minute. I started looking at hotel options but quickly moved to apartments as the cost at this time of year was beyond our budget because we needed more than one room. Two years ago our son was younger and we did book hotels for that trip through Last Minute.

I had been burned five years ago by an airbnb experience in New York, so it was with a lot of research that I jumped back in. Before diving down the airbnb search rabbit hole, I searched for ideas on the best areas to stay in in each of our destinations. My girlfriend Simone also taught me to look for accommodation in the “old town” areas of European towns or cities, so that was a starting point for us as well. With airbnb, search with your requirements within the areas you’d like to stay. Get your head around maps of those cities and towns, so you know where the accommodation sits in relation to where the action is. And look through all the reviews. Don’t be afraid to ask hosts questions. How they respond will be a good indication about how things will go once you’re on the ground. We were stoked with all our booked accommodation.

9 things to do and see on a short stay in Split, Croatia

9.  Research and book any tours you might like to take. We only booked two tours before arriving – one a private day out on a boat on the Amalfi Coast; the other a private day tour to Dubrovnik (from Split). In hindsight, we should have booked Vatican and Colosseum tours for Rome. We paid more on the day to skip the line because time was at a premium and the crowds were ridiculous. Other than that, in Split, it was easy to book a walking tour of the Palace, and on Vis, there were tourist agencies on the ground and even our taxi driver was available to organise a boat tour for us.

9 things you can’t miss on a short stay on Italy’s Amalfi Coast | Luma Charter

10. Research and book any restaurants you don’t want to miss. We love dining out when on holidays. Apart from the “no cook” factor, it’s always fabulous to seek out different dining and food experiences. I searched online, looked to Tripadvisor (a bit but with a grain of salt) and asked friends for recommendations. Then, when on the ground, I was always on the lookout for different options. The great thing that also happened was that Facebook friends posted recommendations on my holiday photos while we were there. At a bar in Positano (that we found via Instagram), a couple we got talking to told us about a restaurant in Split that we couldn’t miss. And so on, it flowed. While on Vis, another friend gave us two recommendations for the island. In Rome, I got a message from another friend. All those recommendations turned into some of our most memorable dining experiences. In a nutshell, let friends (and Facebook) know where you’re going and you’ll get true word-of-mouth recommendations. And don’t expect to rock up to a restaurant and get a table. Book at least one or two nights ahead.

9 things you can’t miss on a short stay on Italy’s Amalfi Coast | Franco's Bar Positano

12. Map out plans for each day but leave breathing space in your itinerary to do something you hadn’t thought of when you arrive at the destination. This is so crucial, I think. Planning is good but not if you end up filling all the chunks of time and not allowing yourself to settle into that holiday feeling.

13. Create a folder in Dropbox (or Evernote or Google Drive) to save all your tickets and documents for travel. We printed everything off but this was always our backup and accessible on our smartphones. In an open Word document, I kept links to all recommended restaurants, activities and tours, adding more as recommendations came in.

14. Think about planning your travel wardrobe a season in advance if you’re travelling to the opposite hemisphere. It’s tricky to shop for a summer travel wardrobe when the only clothes in store are winter ones. I had lost weight since our summer, so a few weeks before leaving I put together my capsule wardrobe to see what I had that still worked. I then had enough time to get some favourite pieces altered. I’d also bought some smaller sizes in my favourite denim shorts a couple of months beforehand. If I’d left all that until the last minute, I’d have been caught short. (For more travel capsule wardrobe tips, check out my e-book).

10 things to do and see on a short stay in Rome, Italy | Travelshoot | Photo by Sebastian David | Hair and Makeup Janita Helova

15. Have fun with your planning. For me, this is so much a part of the excitement and build up to heading away. Embrace it at every step, knowing you’re creating some amazing future memories.

So tell me, what holiday planning tips can you share with us? 


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Comments 34

  1. Wow. So many planners out there with great suggestions. You’ve given some terrific ideas – and like you I pre plan using Rome2Rio, google earth maps , Check my Trip, booking.com, air BnB. When I’ve got it all in place on my spreadsheet I email it and all other important documents ( passport, card details) to myself on a gmail account. We’ve just returned from Slovenia, Croatia ( for a swim trek) and Budapest. All wonderful places. Coming home we had a long stopover in Guangzhou ( we got reasonable priced business class seats with Air France) so got a free room through the airline , took our swimmers for a swim then had a meal and a nap and were ready for our return flight. Arrived home feeling great. Planning the next one in October! And I got the wardrobe pretty well right – though it’s easier in summer when you know it will be hot.

  2. Hi Nikki, By far the best, most useful tool I use when planning a holiday is tripit.com. I only use their free account but with this you can simply forward any of your booking confirmation emails (flights, accomodation, tours, car hire etc) to your tripit account via email. They are then automatically consolidated into an itinerary with all the details you need available online. You can also manually edit these when further information comes to hand (or, if for some reason the booking email you forwarded was not in the correct format for tripit to handle … although this is rare).

    You can also add in any manual items or bookings that you want (such as a restaurants or just the location of a great shop you want to remember to get to!). The intinerary you create can be printed out if you want or forwarded to someone who needs to know your movements. It is accessible online or via an app at any time. In summary .. I don’t go anywhere anymore without using this amazing free tool !

  3. Yes, you can’t do much about the weather can you? Adapt and flow … it was the wind on Vis that meant we had to change up our plans too. We ended up having a day at the apartment around the pool and loved it. Keep enjoying your trip x

  4. Great post Nikki. We spent a month travelling from London to Rome by train in 2013. I used many of the same sites you used for planning your trip. We used AirBnB the whole way as well and found the Seat 61 site invaluable when booking our train tickets. The other big source of info about travelling in Europe came from American tour guide Rick Steves. His website gives you mountains of advice from where to stay to how to avoid the latest scams at the tourist sites! He even has audio guides for the big tourist sites that you download to your phone and play as you roam and the best videos on packing for a month in a carryon suitcase. Well worth checking out.

  5. I’m a big planner too, as we’re fortunate enough to take 1-2 overseas holidays a year. I now have an ‘itinerary’ format in a Word document that gets built upon with each trip, and we work out drive times between destinations, what time/day things open and close, hotel addresses (and type of room booked), ideas for meals, confirmation/booking numbers, which credit card things have been booked/paid against, etc etc. Our itinerary now has grown so much that we even include expected temperatures and whether or not the hotel we’ve booked has laundry facilities! This all came about after a few trips to Japan where we wasted far too much time trying to figure out how to find our way to the ‘east exit’ of a train station, for example! Once we’re happy with our research (usually the day we fly out!), I email it to both my husband and I as a PDF format, and we open it in our iPhones and save to the iBooks app (plus print a copy) so we have it literally on hand. My husband also pre-enters hotel addresses etc into our GPS before we go. My motto is, it’s better to have too much information than not enough (especially if you don’t have reliable wifi access!!)! I also have future ‘dream trip’ itineraries on the go for when I’m scrolling through social media and find amazing destinations that I want to remember! 😉 (Instagram and other social media platforms can be invaluable if you follow a country’s official tourism page!)

  6. Some great tips here Nikki. I too love to plan our holidays and agree that it’s all a part of the fun of the trip. For anyone considering train travel through Europe, I highly recommend it. Travelling by train is an extremely efficient means of getting around, and many of the European train stations are architecturally stunning. As well, you get to see the beautiful scenery on the way, have much more leg room than in a plane, and save quite a bit of money (particularly if you book well in advance- for example, we travelled from Vienna to Prague for $30 AUD each. There is a wonderful website called ‘The Man in Seat Sixty One’ (here’s the link https://www.seat61.com/ ). The site offers advice on train routes and the scenery along the way , including which side of the train to sit on for the best views, links to booking sites (I have used the booking sites many times, and never had any problems), approximate travel times, and advice and photos of the different class of carriages on each route.

    1. Great tips re the train travel Belinda! And the travel insurance with credit cards is useful but doesn’t always cover off on certain things you might need on a trip. As always, it’s about the fine print!

  7. Thanks for a great post Nikki. I plan in a very similar way – much less stressful. I use an app called Tripcase to schedule and store travel details – it’s easy to use and we might even give up paper next trip!

  8. I second the benefit of having access to a lounge for any layovers nor pre-boarding. For those who don’t have gold or similar frequent flyer status there are a couple of other options. If you have an Amex card there are Amex lounges in some locations – Sydney for one (but not Melbourne when I last checked). We also use the Premium lounges, we get a couple of free entries using our Westpac Altitude Black cards and can then pay a nominal fee for any extra usage during any 12 month period.

    1. Ooooh, we have a Westpac Altitude Black card x 2 – do you know if there’s a lounge at Dubai and/or Milan? Or how I find out?

  9. you had yourself a gorgeous trip nikki!
    you planned it well! and it worked for you!
    I am not a planner! … to my detriment at times, but I know that is the way when travelling!
    lucky I have a planner on board!
    that mediterranean water is something else isn’t it!
    we will have to do with queensland for now! … ok by me!
    much love m:)X

  10. Great post. I’m a planner too and I always have several ideas for different trips on the back burner! I hadn’t heard of that Rome2rio app but have already downloaded it! I agree that it’s good to be flexible, particularly when travelling in with kids who are likely to be jetlagged. On a recent trip to NYC , we ended up cancelling a couple of restaurant bookings after big days out and getting hot deli food instead – which was delicious and fun to do!

    1. I love that you have ideas for different trips on the back burner. I’ve got a couple brewing at the moment and seeing how they pan out. You’ll love that app as a tool. Yes to cancelling things when on the ground. Much easier to do this than to book on arrival.

    2. I love that you have ideas for different trips on the back burner. I’ve got a couple brewing at the moment and seeing how they pan out. You’ll love that app as a tool. Yes to cancelling things when on the ground. Much easier to do this than to book on arrival.

  11. Great post and advice! The bit that everyone should not forget is taking out travel insurance from the beginning. We have to travel two hours from home to get to a domestic airport and several years ago found ourselves stopped on the road due to an accident for over 5 hours! We missed all our connecting flights from Townsville to Milan in Italy! It cost us over $3000 but every cent was recovered due to great travel insurance. Best advice, Nikki!

  12. I too am a planner but struggle with over planning my trips. We are one month out of heading to the UK for 3 weeks, our first thought was to travel to Wales and Scotland while we are there, but have given that thought away. We have now chosen 4 different parts of the UK to base ourselves in, ready to explore. Your post has made me even more excited than I thought possible! xx

  13. We are currently planning our first family trip to the Gold Coast and Sunshine Coast. Have accommodation booked and flights, insurance etc. But now would like to find the hidden treasures in those areas. Do you have a blog post of yours you could point me towards or one that you follow. I know it isn’t Europe but we aren’t quite there yet $$$ wise!

    1. Exciting! We love Burleigh Heads on the Gold Coast https://www.stylingyou.com.au/2016/01/10-things-to-do-in-burleigh-heads/

      This post might help: https://www.stylingyou.com.au/2013/09/things-to-do-on-the-gold-coast/

      And these from the Sunshine Coast:




      1. Thanks so much Nikki! I have read your posts and added loads of stuff to my Pinterest page. I love to research wherever we are going before we go so we get to make the most of the trip. As a result we have had some incredible trips around NZ (we live there).

  14. Totally agree. I’m a planner too…….that 3 weeks in Canada at Christmas…..I had the sheet out with where, when, what etc. but had our down time too. All Anthony knew was when we flew out and Canada lol……I had everything else sorted…..go the girls. It’s great going to off the touristy places too. Wonder where too next…..for you (and me ❤)

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