More and more people in the younger generation are now planning their own free-and-easy getaways, whether it is because they want to save money, want more privacy or just because they are control-freaks. Being a control freak myself, I do prefer planning my own trips much more than joining a tour group.

For me, it started off by planning short road trips into Malaysia’s Malacca almost 10 years ago, and then to longer and longer trips. The more I find out about a place, the more I realised the process of planning is as fun as the destination! The last road trip/tour I’d planned was to the USA West Coast, a complete Self-drive 14-Day adventure.

I find that l, with numerous self-booking online tools and review websites, it is easier and easier to customise a getaway that is catered to you. (This is probably why more tour agencies are going out of business. Sorry not sorry!) It is something to be thankful for as I remembered 20 years ago when my dad brought us on a 10-day New Zealand road trip we didn’t have the luxury of the Internet and these tools. What you got was a guidebook, some paper maps and stopped and visited wherever there was an “attraction” or “accommodation” along the route. I suppose it was very stressful for my parents and my younger brothers but I was impressed with the joys of a road trip at that age.

First of all, you have to ask yourself if going Free-and-easy is suitable for you:

  • Do you like adventure?
  • Are you travelling as a single, a couple, with good friends and/or older (independent) children?
  • Do you cope well with new experiences, even unpleasant ones?
  • Do you have time???

Going free-and-easy can be a really enjoyable experience, or it can be a nightmare. It all depends on your mindset and preparation.

First: Decide Where You Want To Go

I’m sure you already have an idea of where you want to go! Inspiration comes from anywhere: friends and family, television, books etc. Once you decide where to go, it is time to start researching in detail.


Second: Look at Itineraries

Itineraries gives you a realistic plan of duration and places you can visit in your preferred travel location. For example, if I realised that 5-7 days is a realistic plan for touring Kyushu. Looking at other itineraries also gives you a good idea of the places of attraction and a general skeleton for you to start building your fully personalised travel itinerary. My favourite sources of itineraries come from tour agencies (touché), travel blogs and websites like, after all, they did most of the hard work and we should benefit from it.

Third: Customize and Personalize!

This is the most time-consuming step. Depending on the length of your trip, it will take you months to plan it from start to finish. Thankfully we enjoy the planning process so much right? Believe me, it will test your perseverance and strength. At times I felt like giving up and just going to a tour agent.

In this step you have to start bookmarking and favoriting all your research. I always start from TripAdvisor. For each city/town/location I’m going to stopover or visit, I read up on hotel reviews and places of attractions. Decide on whether the attraction suits your personality and preference. For example, if you are the active explorer and adventurer, then you can save all the nature hiking and extreme sport locations on TripAdvisor to your custom itinerary. I prefer a relaxing discovery trip so I usually would look at nature spots, National Parks, historic hotels and museums.

Once you shortlist a number of places, it is time to start looking at routes.

Fourth: Location, Location, Location

A common lesson I learnt from planning trips is under-estimating travel time. I was overly ambitious in my first few road trips and as we only have so many “active” hours a day, we ended up skipping most of the attractions. Whether you are self-driving or taking some kind or public transport or even walking, you will encounter many factors that affect travel time, some of which are:

  • Public transport timings
  • Self-driving: Looking for parking lots
  • Traffic conditions
  • Weather!
  • Getting lost
  • Bathroom breaks
  • A slow travel partner
  • An unplanned but interesting hotdog/popcorn/attraction stop

Although I recommend the highest discipline when it comes to keeping within the schedule, always try to plan for surprises and allow lots of time between destinations. It makes the trip so much more relaxing and enjoyable!


Because of this, I always add about an hour or two to the travel time. For example, travelling from Singapore to Malacca takes 4 hours but I will plan for 5 hours and plan the other destinations in the same way. If you arrive earlier, then you even get to spend more time at the attractions.

Time-Saving Tip: My travel plan usually consist of travelling from hotel to the attraction and back. I personally don’t ever plan for meals or dining, unless it is a foodie trip. Most of the popular restaurants that you find on TripAdvisor or Yelp are especially hard to get into and require advanced reservations. Usually I would just eat at the attraction or nearby. I find that you tend to snack a lot when travelling and also strangely become hungry at all the weird hours, so it is hard to predict when you’ll feel like eating on while travelling and make reservations. Of course, you may disagree.

For travel times, I turn to Google Maps and simply search for directions from Destination A to B and see their estimated travel time. For a reasonably enjoyable day, especially for long road trips, try not to plan more than 4 hours of driving in total in a day, unless absolutely necessary. It is tiring on the driver and even for all your passengers.

Focus on the things that matter and don’t try to do too much! Give yourself time to savour each place rather than rush through it.

Fifth: Budgeting

It is always good to have a rough ballpark budget before you even go on a trip. After all, some places are cheaper to visit and some are more expensive. However at this stage we start the seriously budgeting process for hotels, transportation and even food. Doing more research in forums and asking friends will help you understand the costs of each city. Try not to be a miser on your vacation! Always budget generously. These are just some items to get you started:

  • Flight tickets
  • Bus/Metro/Train/Ferry/Hot Air Balloon
  • Car Rental: Most of my other transport fees come from car rental.
  • Tolls: If you are driving.
  • Accommodations: I prefer to select hotels or B&Bs or home stays along the route and near to the center of the action. Convenience over costs as I will save a lot more time on travelling around and food places.
  • Dining: You will be dining out most of the time and it will get expensive! Be sure to budget quite a bit on food. Although you can’t definitely confirm the price of the food until the day itself, you can budget a limit per day for food, e.g. $100 a day.
  • Tips for services
  • Gifts and souvenirs to bring home

We however do not recommend bringing too much cash into most countries due to safety. Because of this, find the best credit card plan which offers the lowest conversion rates and some even offer free travel insurance as well!

Sixth: Final Preparations Before Lift Off

Certain things tend to be left out while you are planning for the trip. Since we have covered a few items above related to your trip preparations, I’m going to highlight some things that you should check before leaving:

  • Tourist taboos: Always remember that you are a tourist and just a visitor. Stay humble and learn the culture of the place. Some have strange traditions which have to be observed and, unless you like to be embarrassed or irritating all the time, you might want to read up more about their culture.
  • Bring a small first aid kit: Mine always includes plasters, charcoal pills, paracetamol and Fybogel. The most common kind of illness while travelling is actually stomach trouble as you might not be used to the food so I bring a variety of digestion related pills.
  • Stay healthy: Sometimes a hectic travel plan will make you fall sick so in order to be most prepared before you go, eat and stay healthy, sleep well and be on your best! I usually don’t take vitamins but I like to take more Vitamin C a few days before I leave on a long trip. You can also bring some along if you are travelling longer than a week.
  • Pack smart! There are lots of travel tips online on what you can reduce and should pack. It all depends on where you are going. Try to leave a big empty space in your bag or bring an extra foldable bag for all the goodies you will bring back.

Hope these tips help you on your next trip and remember, it is all about exploring, relaxing and new experiences! Enjoy each moment.