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A Guide On How To Plan Your Trip

Planning a trip can be daunting if you are not familiar with international travel.

There are so many questions that come up not only while choosing the destinations but also when it comes to planning your trip and getting things done.

I have planned many trips for myself both privately and for work and over the years have developed my own planning ritual that works well and help me save time and money.

That’s why I have put together this guide to help you through the process of planning a trip, which you can use for short holidays as well as long-term trips.

1. Choosing travel destinations

First a word about choosing travel destinations which may seem easy, but it truly isn’t.

While in the past it was easy to choose among many destinations, nowadays people are often torn when deciding where to go on holiday. Knowing the destination or using a quick decision process will make things much easier when planning your trip.

This allows you to keep your focus on one destination instead of evaluating multiple destinations, because this is going to drain your energy. There are way too many factors that influence us when choosing our trip destinations and make our choice difficult at times.

Travelling involves adjusting to new places with different cultures and environments. By choosing destinations that are safe and easy to travel around you are doing yourself a favour.

Tips for choosing stress-free travel destinations
  1. Avoid destinations with critical political situations, civil unrest and conflicts.
  2. Prefer destinations that don’t require extra medical checks, vaccinations, etc.
  3. Make sure your destination is safe for travellers.

That being said, travelling is a personal choice and the level of risk you decide to take on your trips is your responsiblity. However before start planning a trip, when in doubt, please check these useful sites for travel restrictions, travel alerts and travel warnings.

Find Inspiration and advice on your destination
  1. Read Travel Blogs about your favourite destinations.
  2. Post questions on Social Media Travel Pages or Groups.
  3. Reach out to friends for inspirational travel stories.
  4. Read Travellers Reviews about destinations and landmarks on TripAdvisor

2. Booking Flights for you trip

Once you have identified the destinations you want to travel, the second step of planning a trip is to book the flights. If you travel peak-season like Christmas, Easter and summer holiday, June-August for Europe and US you must start your search at least 8-10 months ahead to make sure you get a good flight deal. If you travel off-season then 3-4 months is good time to plan your trip.

A Guide On How To Plan Your Trip

Airlines start promoting their deals between 6-11 months ahead, depending on the destinations, so it’s a good idea to set flight search alerts from various airlines and get them delivered into your mailbox. Airfarwatchdog is a good site, if you are flying from the U.S., to set up airfare search alerts.

Best Travel Websites for booking cheap flights

These are my favourite travel websites for booking cheap international flights:

  • Skyscanner
    the most popular search engine for comparing international flights, it’s the visually user friendliest travel website so for newbies the best site. I use the platform for all my flights.
    I use this excellent tool for finding great deals on one-way airfares, if you book single flights-legs that’s the best place to look for.
  • Matrix.ItaSoftware
    Powered by this is similar to but with a more classic search criteria.
  • Kiwi
    less known than other sites, in my opinion this is one of the most powerful online sites for cheap international flight. The website’s layout is lacking a bit, but once you get used to it, you will love this site.


Check out this other page with top-rated Travel Planning Resources.

3. Travel Visas – How to apply

The third step is to get your travel visa for your trip. For some countries you will not even need one. Your valid passport will be enough, but in this case be sure your passport is valid for at least 6 months from return-flight home. This is a pre-condition for many countries and you may get inconveniencies if do not comply with this rule. Applying for travel visas for Australia is a no-brainer (it takes 5 minutes to fill in the online application form). To apply for multiple countries or countries that are requiring more docs, it’s advisable to use a travel visas service.

  • Check this page on how to apply for your travel visa for Australia.
  • For travelling to the U.S. you will need the ESTA if you are from this country list.
  • For Australian travelling to European countries check this page here.
  • If you travel to a country that requires vaccinations and good health proof make sure you comply with their requirements and get vaccinated.

Use  Travel VisasHQ as a fast, reliable service when applying for travel visas.

4. Create a trip itinerary and plan activities

Once you have your flights booked to your destinations, then you need to give shape to your trip and create an itinerary with activities, domestic transportation, things to do and see. If you have a clear focus on what’s the purpose of your trip, it will be easier to set up an itinerary. You can look online and read travel blogs about the destinations and put it together by yourself or you can ask a travel expert to help you choose what to do, what to see and further planning and organising your trip.

These resources will help you get your itinerary set up and also find tours and activities.

  • Check Destination Pages on Facebook, Boards on Pinterest and Posts on Twitter.
  • Read Travel Blogs – they are the most reliable source for the first-hand experience.
  • Browse through Tourism Boards sites – they have downloadable maps.
  • Visit the Tourist Information Centres – find orientation about the place.
  • Get advice and custom itinerary from a travel planner.
  • Check out top day-tours for Italy for the USA, and for Australia and +200 destinations in the world.
Australia Travel Planning

If you are planning a trip to Australia you can browse through hundreds of pages and posts here on the Rocky Travel Guide. With +13 years of solo travels around the country, I have put together nearly 100 thousand km so I am here to help as your trusted travel expert.

Use this break down categories to quickly find what you are looking for:

  1. Get Your Australia Travel Itinerary Book
  2. Read this blog post on how to plan your trip
  3. Use these tools for organising your trip to Australia

 Get help while planning your trip, check out my  Travel Planning Services.

5. Book Accommodation

Booking accommodation is something that I would always do before leaving home if you are planning a trip of a couple of weeks, but I wouldn’t book for the entire trip if you are travelling for months. On long-term travels it’s more convenient to make spontaneous decisions on where to stay and booking your accommodation locally. Also if you are travelling off-season you may want to book for 2-3 days and then make further arrangements on the spot.

If you travel on a budget and solo then staying in a hostel could be the best option, but nowadays you can use more resources like airbnb has become my favourite option for my solo trips.

Create your profile and get 35 USD (or equivalent) off your first Airbnb booking.

If you prefer the comfort of a hotel you can browse and find deals with:

    I started using 12 years ago and loved the great deals I could get over weekends. One of the pros is that is the free cancellation feature that is offering huge flexibility.
  • Hotelscombined
    I started using hotelscombined in Australia because it shows properties from over 200 places. This search engine is great at comparing prices from sites like,, agoda and more.
  • Wotif
    It’s the most popular Australian travel website for booking all kind of accommodation and find great holiday packages within the country.

6. Get bank-fees free Travel Cards and Debit Cards

When you plan your trip overseas you will likely need a travel card and a debit card for making online booking (flights, accommodations, tours, etc.) and withdraw money from ATMs.

  • Beware that with a debit card you will not be able to pay everywhere. For rental cars and more services in many countries they only accept credit cards. So you need both!

On my first long-term trip around Australia I used my credit card to withdraw cash from ATM to realise, back home, the money I had wasted on bank fees as well as exchange rate fees. Money that I could have saved and spent on other things while travelling. Since then I have learnt how to reduce the cost on bank fees by 75%.

U.S. residents are the luckiest, thanks to their local banking system, there are a few banks that offer credit cards with fantastic reward plans and many have zero fees too.

Here are some useful resources and websites:

  • This site for the best credit cards with no transaction fees for the U.S.
  • In the United States the Charles Schwab Bank has no annual fees and offers monthly reimbursements of all ATMs fee that you use from any bank round the world.
  • Australians can use a CitiBank Account which offers credit cards with no ATMs fee.
  • For Europeans, this varies a lot depending where you reside.
  • For Italy I would highly recommend postepay evolution credit card which has the cheapest administration fees and low ATM fees overseas.
How to withdraw cash when travelling

While almost every travel card has a currency converter fee and Debit cards is the way to go. Don’t use credit cards to withdraw money from ATM but instead use your debit cards because bank commission are usually lower. I stopped changing money into cash before leaving home. The first thing I do is withdrawing money from an ATM after arrival at the airport.

My Tip: a good thing to do is to check with your bank and ask them to give you a list of correspondent banks in the countries taht you are planning to visit. Bank commissions are usually lower, sometimes 50% or even lower than using your card with ATM from other banks.

7. Travel Packing light

Of all planning tasks, travel packing is what takes the most time to master. Over the years we change our habits and travel style so we need to adjust our packing style too. I have learnt to reduce my packing weight from 25 kg to 15 kg, but it took me years to learn how to travel in a minimalist way. When we travel we tend to pack way too many things that we don’t need nor use in our trip. So it’s really worth working on this aspect.

Travelling light is an art that you need to develop over the years. Lots of trial and error belongs to it. I find that choosing the right type of luggage has helped me on this process too. I prefer using different luggages depending on the type of trip.

One more thing I found vital is using suitable travel organizers for important things. One I find very useful is to get my toiletries organized.

These posts will help you pack smart.

8. Purchase Travel Insurance

While, according to statistic, only 30% of travellers buy travel insurance, for the cost of 2-3 dollars a day it really makes sense to be covered. You never know what happens when you are on the road and if something happens it can easily cost you a few thousands dollars.

Travel insurance goes beyond the domestic health plan coverage, it includes everything from booking cancellations to theft of personal items, to personal liability and the most important the health coverage.

From 2012 I have been using travel insurance from WorldNomads and love their flexible plans. I can extend it and on my long-term travels I can purchase it on the road too. You can do everything online, from purchasing to getting asssistance 24/7.

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A Guide On How To Plan Your Trip
A Guide On How To Plan Your Trip