How I planned a long holiday to help you plan yours

imagesAnother flight booked, this time it’s a long one. This will be our first long holiday, just under 6 weeks. I can’t wait!!

Now my son and I love to travel. His now 3yrs old and hungry for that next flight to paradise. This will be his 7th trip out of our city (Sydney). We love to follow the sun and have been fortunate enough to have travelled to a few destinations.  It is a little bit harder, don’t get me wrong but we love it. To be able to enjoy travelling with him is all worth it. You can do it too. My son doesn’t hold me back, rather he brings out the life in me. Your kids will love it and it’s a great experience for them. Bring on the joys of travelling with kids.

This is where I step in and tell you how I planned our holiday to assist you in planning yours. It can be a long process but it is all worth it. One stop destinations I generally ‘wing it’ with a little bit of research. Write down a few things there is to do and see and when we arrive we can choose the best option for us. A multi stop on the other hand I have found it is best to be organised in order to maximise the limited days spent at each destination. It is also important to draw out a rough itinerary in order to organise how many days best fit each place.

Although we have made 7 trips out of our home state, I have learnt much from organising a multi stop holiday. This will definitely assist me in future travels.

First things first, booking flights. Taking that first step and booking that flight means you are commiting to it. You are more likely to try and save every dollar you can to make it a trip to remember.

Flights were on sale to Phuket flying Jetstar direct for under $300 return. I just couldn’t pass up on a good deal. I paid a total of $649 for my son and I, including 20kg baggage departing Sydney and 45kg arriving in Sydney. When purchasing baggage I always try to make sure I have enough but if need be I have the 7kg carry on for both my son and I. That’s an extra 14kg backup just incase. If you need more baggage than purchased, make sure you purchase prior to check-in. The fees are absolutely ridiculous once you have passed the window allowed to purchase more baggage. Of course purchasing it upfront with your flights is the cheapest option. Travelling on my own, I don’t like to take carry-ons with me unless need be, except for a backpack containing essentials. If you are happy to take carry-ons, you won’t need to purchase as much, unless you think you will need it. Check your airline baggage allowance. Most airlines allow 7kg carry-on and a personal item like a handbag or backpack, total weight allowance of 10kg. I take a set of digital baggage scales with me to check my weight to make sure. There’s nothing worse than getting to the airport all ready to go and then having to rearrange your luggage because your check-in baggage is over weight at the counter. It also depends on the airline. Some airlines are stricter than others and others allow you to combine the total weight of all passengers boarding.  Particular airlines also have a max weight per bag. I have flown Thai airways before and was well over the limit by over 20kg and was fine to board without further charge. That was when I was a lot younger though. Now I wouldn’t risk the excessive charge.

The planning and researching that needs to go into a long holiday is time consuming…it will all be worth it. There needs to be lots of researching. Itinerary is open as only my return flight is booked. It allows me 9 months to save, research, book accommodation and internal flights.

First I had an idea of where I wanted to visit. Of course I wanted to visit more than I could fit in, so I had to cut out what I didn’t think was worth the time flying and visiting on this particular trip. I also looked at the prices for flights and to visit Hong-Kong would have cost over $500 for flights alone so this made my decision a lot easier.

Next step, I researched what there is to do and see at each destination. Keep a note pad and write down everything including prices and websites so you don’t leave out any details. I separate each destination so everything is easy to find. Of course all these plans will change as you do more research, try to work out a rough itinerary in order to work out how many days you will need to stay at each destination, where you will be staying and if things are worth doing and read reviews. There is an abundance of things that will change as you conquer each process and do more research. Hopefully this blog will help you to plan your own trip with less stress. You can do it! Check out my blogs for each destination for more details.

Trying to work out the dates for each flight accordingly, don’t be in a rush to book anything if you have plenty of time to research. The internet knows what you have been searching. It will send you emails and facebook feeds on the locations you have been searching. Prior to booking anything, make sure you delete your cookies as prices can fluctuate the more you search.

The reason I research on things to do was to give me a rough estimation of days spent at each destination. Then I worked out how many days spare I would have so I could space out my itinerary and add days where need be. Make sure you have a look at where things are so you can go to places that are closer to each other on the same day if you can fit them in, so you are not wasting your time travelling from one place to the next on different days. Where would I want to stay longer, where was it worth staying longer and also remember to fit in days of relaxation and shopping. 

My itinerary thus far is Bangkok, Kuala Lumpur, Penang, Singapore, Koh Samui, Koh Tao and Patong. Am I biting off more than I can chew? I don’t think so. I can do it and so can you. Remember if travelling with kids that things just take longer, so consider this when planning. You also don’t need to do everything on the bucket list if there isn’t enough time when you’re there. Work out what you really want to do and see and the things that you can miss out on if you can’t fit it in.

From previous experience of travelling to Asia, I don’t pre-book any tours online. It is much cheaper when you get there and you can score yourself a discount. Every destination is different. Some places give you a better conversion rate when you are there such as Asia, other places will give you a better conversion rate here like America. When we went to Hawaii the rate was much better purchased here. Remember to research though. For instance tickets to safari world in Bangkok can be pre-purchased online cheaper than at the door, whereas the crocodile farm in Bangkok is cheaper to purchase at the door. Tours aren’t always the way to go. Sometimes if you do it on your own it is much cheaper and you can come and go as you please, whereas going on a tour means you will be picked up from the hotel along with all the other tourist making your day much longer. You will also have to meet at a certain time to leave.

After getting a rough idea of how many days I will be spending at each destination, I used skyscanner to search flights to give me a rough estimate of how much flights would cost. With a rough estimation on flights using both international and domestic airports, total for flights are approximately $1200 for my son and I. That’s $600 pp including baggage for 7 internal flights and 2 ferry transfers, all direct except the flight from Singapore to Koh Samui which involves 2 flights. From Singapore to Phuket, Phuket to Koh Samui. The reason I did a layover here is, it is saving me $220 and the flight times to Koh Samui will mean I arrive at 12pm so I still have time to enjoy the day. Choosing to fly direct will mean either getting there at 9.30am, 6.30pm or 9.10pm. I may still change my mind as it hasn’t been booked. I am still weighing up my options. To arrive 2.5hrs later to save $220 or to fly direct and spend the extra money. I could also fly at 5.30pm and spend the day in Singapore to arrive in Koh Samui in time for dinner. It also depends on your itinerary, do you want to be spending that day there and then fly at night? Even still, if I choose to fly direct, the total would be $720 pp for all flights and ferry transfers. That’s a pretty amazing deal. It is almost like flying direct from Sydney to only one destination which isn’t on sale. Using the domestic flights and airlines for that particular country is a lot cheaper than booking every leg here with a travel agent or even on your own as you would probably use airlines known to us. Also using the domestic airport as opposed to the international airport will also save you some money. Have a look at how far the domestic airport is vs the international airport to where you will be staying. Generally I like to stay in the city centre where everything will be close and walking distance. Of course this comes with a higher price tag. You can find some cheaper accommodation though. Do you need to stay in a really nice resort for a higher price? Is this your priority? For me, not so much. My priority is something clean and close to the city centre, walking distance and convenience. Do you have time to use the facilities? If not, opt-ing for something without facilities will cost less. Most rooms will be costing me less than $100pn. I would much rather be spending my money on my holiday than a hotel room where I won’t be spending my time in. In saying that I will be spending a little bit more in Koh Tao and Patong where I will have time to use the facilities. Even still you can find rooms at a relatively good price. See where I will be staying and more details on my blogs for each destination.

Once you have worked out where you want to go, to get a rough estimate on flights, shuffle your itinerary around to see if flights from one destination is cheaper than another, duration of flight and flight times. For me, travel time is a priority. I only look at direct flights as I don’t want to be spending my holiday on planes, especially with a toddler.

Using foreign airlines also means you will have to check their policy for baggage allowance and free items such as a pram. Most airlines I found included enough baggage. I will go into more detail of which airline I chose and their baggage allowance on my blogs featuring each destination. Stay tuned and follow us to South East Asia. Hopefully I will inspire you to take the plunge! You only live once. I say DO IT! Even with kids it is manageable. I have done most of my travelling since having my son and it has been an amazing experience to be able to share it with him. Best advice I can give you is to remember it’s their holiday too. Incorporate things that they would enjoy doing as well as things you would enjoy doing. At 2.5yrs old I took my son hiking Diamond head which is a volcanic crater in Hawaii. You can take your time. It is possible. My son does not hold me back in doing anything, rather he brings out the life in me.

Now I have worked out an itinerary, how many days to stay at each place, where we would like to go and see and spaced out my itinerary, its time for the harder decisions. Which hotel to stay at.

I used to do an initial search of what was available. I searched one leg at a time and created a shortlist. Try to make as short of a list as possible. Narrowing it down to choosing which one you will be staying at and the cost of it will make it easier to make a decision later. offers stay 10 nights, get one night free. The free night is then credited to your account 72hrs after checkout. The free night is based on the average spend over the 10 nights so spending $50 per night will not land you a 5 star room free for one night. Don’t get sucked into gimmicks, have a look at their fine print. I then used airbnb and found some great places for roughly the same price as my budgeted accommodation found on Using airbnb you may be able to find the same hotels which are privately owned at a cheaper rate. Sign up for Airbnb and get $50 AUD off your first adventure.

Remember that every dollar counts. Every dollar you’re not spending on your accommodation goes towards spending money. After checking airbnb, again create a shortlist. Compare it to the shortlist created on, then again create a shortlist of the combined. By now you will have an idea of where you would like to stay. Use other sites such as agoda, wotif, trivago and to compare prices and other accommodation available. Make sure you check your dates to see if they are available especially on airbnb which will allow you to shortlist even further. Also remember to check with the hotel directly on their site to see if they offer a cheaper rate.

After much research, I decided to opt for something nicer and spending a little bit extra in Koh Tao and Patong where I will be doing more relaxing. Saving at the other destinations means I CAN afford to spend a little bit extra for a nicer room at the end of my holiday. Every dollar adds up. “It’s only an extra $5 per night for the nicer room that I won’t be staying in” can all add up over the 6 weeks.

What is good with airbnb from previous experience is that you get a personal local who can give you some good tips. Depending on your host of course. When we stayed in Hawaii, our host was a great help and saved us loads of money. Fingers crossed you get a great host. Read reviews on the place and their description. I did come across some where host is unable to meet you but are happy to answer questions via text or email. Staying in an airbnb also means your linen and towels won’t be changed unless staying for longer than a certain period of time. Again you need to ask yourself if these things are a priority or can you live without. I mean we don’t change our linen everyday at home do we?

While I haven’t booked anything yet, my itinerary is set and I know what my dates are for flights and accommodation. Now its time to have a closer look at things we will be doing. Searching for the cheapest option and penciling everything down so our trip will be a smooth one. You may also want to check out where you would like to eat, restaurants, well-known must eats and shopping spots. Talk to people you know that have been there and secret spots they may have discovered. Join facebook pages for travelling, people are more than happy to share a few good tips with you if you ask. Search on the exchange rate and reviews others have mentioned on their experience to that country. Doing a more detailed search on the things you will be doing for prices, location, how long it will approximately take you incase you may be able to fit something else in on that same day and whether it will be worth doing or if it can go on your list of ‘can miss out’. I searched each place one at a time and did a thorough search, penciled down websites and prices and worked out which day best to do each activity. Remember to space out your full days with not so full days in-between if travelling with kids. It will take it out of them, and there’s nothing worse than a tired and cranky child. Researching thoroughly can save you a lot. I did this before booking any flights incase I needed more days at a particular destination or if I could free up some days. When doing a thorough search you may also come across other things there are to do. Although I have researched and found the cheapest option to do everything, I won’t be booking any until closer to the date. You can discover where we will be going and my experience. Check out my blogs and follow me as we see the world.

Itinerary – check, accommodation – check, activities searched, time to start booking. Make sure all your dates and times for flights match up and as you book, make sure to pencil everything down. It doesn’t all need to be booked at the same time, hence booking so far in advance to save up.

Travel insurance. I have found that travel insurance can vary depending on the company. For one destination it can add up to around $200pp depending on where you will be travelling to. Check your credit card benefits as most come with free travel insurance when paid on your card. Also check out annual travel insurance. I have been using and purchasing an annual package which is around $250. It also gives me more cover. The price will depend on if you will be travelling to North America or not and how many days you will be travelling for. You can purchase insurance for 30, 45 or 60 days on any given trip. I used when we travelled to Hawaii which worked out cheaper as I purchased for the year. This also covered us for our trip to the Whitsundays. Have a google for discounts. I found a 20% off travel insurance with groupon for for free. Remember though that all insurance have very tight clauses in their policy. My main concern to purchase travel insurance is for medical and incase we can not go. Another benifit with is children and grandchildren are free under the age of 18.

Remember to check if you need shots! When travelling to Asia you will need some shots. It can become quite expensive if you plan to travel quite a bit. To minimise long-term costs, get the booster shot within the timeframe. This will cover you for your lifetime.

Another thing to look at is if you will need a visa. Some countries require a visa if you are visiting prior to departure and others may be purchased upon arrival. The destinations we will be visiting do not require a visa for the specified time we will be staying.

Follow us on our travels and check out all the destinations and what we will be doing. See how I managed travelling with a toddler and all the sites I used for best prices I found. Keep an eye out for my upcoming and previous blogs and adventure with us.

Are you ready to plan your next holiday? Unleash the travel bug in you. The world is your oyster. Take the plunge, you won’t regret it.

@diaryofasinglemum signing out


30 Comments Add yours

  1. mummymanderz says:

    I’m coming to you on our next travel itinerary. Won’t happen for a while but when it does. I know who to go To! Lol


  2. allmydealsindia says:

    Such a beautiful post left me speechless in the end. Would love to go on a holiday

    Liked by 1 person

    1. You can do it! Take the plunge it is so worth it


  3. Ty Knighten says:

    I need to plan a holiday for sure. I have to say, your planning is impeccable. You may be my next travel agent. Great post!

    Liked by 1 person

    1. Thanx. This is actually the first full planned itinerary i have done. After a few months of research my itinerary is finally done. Hurray! If u need any help pls pm me


  4. The Recovery Republic says:

    I need a vacation URGENTLY

    Liked by 1 person

  5. A lot of good info, I think I need you to plan my next vacation! Most of the time we just ‘wing’ it! Lol.

    Liked by 1 person

    1. Lol i usually wing it also when im there. Multiple stops needs planning especially with a little one in tow. Need to make the most of the numbered days we have

      Liked by 1 person

  6. Flying used to be so much simpler, back when airlines gave a lot more leeway on everything. Now they’ve all got so many different rules, and trying anything to charge you. Such a hassle! Good write.

    Liked by 1 person

    1. Absolutely agree. They will squeeze every dollar they can from you. I hear now jetstar will be charging $15aud for every 1kg over


  7. In and Out of Vegas says:

    Some really great tips!

    Liked by 1 person

  8. CareOn Skin says:

    Travelling is one of my favorite thing to do.. especially when I’m with my family. Wow! this post really provides details of planning a trip. Good job!

    Liked by 1 person

    1. If i won the lotto i would pack my bags and travel! Im fortunate enough to be able to experience it with my son


  9. breakthefog says:

    Even though I love traveling… I am such a mess when it comes to organising it!!!
    Thank you so much for sharing these useful tips!!!

    Liked by 1 person

    1. Not all places need a detailed itinerary. All depends where u go and have a rough idea about what there is to do. I generally wing it but multi stops definitely needs a plan.


  10. Maria says:

    I love travelling and I think this is such a helpful article. Loved reading it 🙂

    Liked by 1 person

    1. I hope i have inspired u to take the plunge. U deserve it


  11. I know a few people who have gone to Singapore and I’m told it’s amazing. Your article was very informative and it looks like you know what you’re doing when it comes to planning a vacation.

    Kimberly Love, Author,, writer of the Upcoming novel, You Taste Like Whiskey and Sunshine,,,

    Liked by 1 person

    1. This is actually my first trip with multiple stops. Having a toddler and travelling alone means everything takes longer so i need to be prepared! Cant wait. Not long to go now


  12. roadaviator says:

    Your article is amazing! Traveling is my favorite thing and the tips or planning that you have provided will help me more to plan my long trips.

    Liked by 1 person

  13. Traveling is fun but planning for a trip becomes tedious. Starting from itinerary to bookings to packing – planning a vacation is one heck of a thing. Thanks for sharing some great tips about planning a holiday. They sure are helpful.

    Liked by 1 person

    1. I usually wing it when i get there but i think mutiple stops need to be planned out to make the most of it.


  14. Great tips, I usually forget the most important two. Shots an insurance. I wish I was as organised as you

    Liked by 1 person

    1. I usually wing it when i get there with a little research depending on where you are going. But a multi stop needs lots of researching to make the most of the numbered days. After a few months of researching i have finally finished our itinerary 😁😁


  15. This makes me want to take a holiday right now.

    Liked by 1 person

  16. bcalmncool says:

    Detailed experience.. Good guide for frequent travellers.

    Liked by 1 person

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