How to travel like a pro

I often take for granted how much work is involved in planning a trip. 

I hear from friends how they saw my pictures from South East Asia or Europe and wish they could do the same. When I ask them why they can’t, their responses can be surprising. 

Many of them say that traveling is too complicated, or too expensive, or they’ll come up with some other reason for not exploring the world. 

I agree that travelling can be both complicated and expensive, but hopefully reading this post will help. I’ve outlined the process that I go through when I travel.

1. Decide where you want to go

When planning a trip, naturally the first thing you want to do is decide where you want to go.

With any trip, there are basically two options:

  • Somewhere old (been there before)
  • Somewhere new (have not been there before)

For the purpose of this post, I’ll assume you’ve selected to go somewhere new since that is the more complicated of the two choices. 

Knowing exactly where you want to go is different than just having a general idea of where you want to go. For example, “I want to go to Europe” is different than “I want to go to London” — two common statements; two totally different procedures.

PRO TIP: Look into neighbouring cities / countries to visit as well. If you're planning to spend a bunch of your hard-earned money and effort to travel abroad, why not see what else is in the neighbourhood? This also relates to how long you want to spend in one place and also how much time and money you have. Nevertheless, it’s good to optimize your trip.

2. Decide when you want to go

Once you’ve decided where you want to go, you have to determine the dates. This actually entails two decisions:

  • When in the calendar do you want to go
  • For how long do you want to go

Booking a trip that is less than a week, and to only one city, is very different than booking a multi-city trip that’s over longer than a week.

PRO TIP: If you have a bit of flexibility on your dates, sometimes flying one or two days earlier / later can affect the price significantly, and on some sites, you can view the fares of multiple dates at once which is very convenient when you’re looking for a good deal.

3. Look into finances

Deciding where and when is a start, but you have to determine whether you can afford to go.

I assume that if you are serious about planning a trip, you have a little money stashed away, otherwise it’s just a sort of wishful thinking exercise. The point is that often we don’t know how far our money will go. Two thousand dollars for instance is enough to travel some places, but not others.

Looking into finances comes into play in three main ways:

  • How much luxury (comfort, convenience, views, safety, activities, etc.) do you want in your trip?
  • What are the exchange rates (i.e. how far will your money go once converted)?
  • How expensive is the country you want to go to?

 

The biggest expenses are typically flight and hotel. Certain parts of the world are cheaper to fly to from where you are than others, and this can vary drastically.

Hotel prices vary a lot as well. In developing countries for instance, you can get a room for $20/night vs metropolitan cities that could cost $400+/night.

4. Look at weather

Looking at weather sounds pretty straight forward, right? 

You may want to go somewhere sunny and pack appropriately. Going to Mexico, for instance, with a luggage full of tank tops and board shorts will not be good if it’s raining the entire time.

However, there is one very important aspect of looking into weather — you want to see what is the best season to go. There are three travel seasons:

  • Low seasons refers to really miserable weather conditions, few tourists, really cheap, and overall a bad time to visit. Picture Hawaii during monsoon season = not good.
  • Shoulder seasons refer to an off-peak season usually spring and fall when airfares and accommodations tend to be cheaper. It is ideal for when you want to go somewhere and see some things for a relatively low price. As an added benefit, you often experience fewer crowds. The downside is that the weather may not be suitable.
  • Peak seasons are more popular times to go when the weather is nice or when it conforms to common holiday cycles i.e. summer and Christmas. As the laws of supply and demand dictate, when an influx of buyers desire something of a fixed quantity, the price goes up. In other words, what you gain in terms of good weather and time of year, you lose in it being more expensive, having more crowds, and more sold out accommodations and activities.

PRO TIP:
If there is a particular natural attraction you want to see, check when is the best time to see THAT since it could be that it’s in the low season for that region, but that particular attraction looks best then.

My colleague was telling me how when she went to China, she really wanted to see this particular forest that had lots of nice plants. They went all the way to China just for this one thing and when they got there, none of the plants were in bloom. Aside from being really disappointed, they also wasted their precious time and money to visit a place at the wrong time. Don’t let this happen to you.

5. Look at airfare / accommodation deals

When trying to find the best deal on flights, you can use sites like Kayak or Google Flights to help track flight prices and alert you when there are sales.

Sometimes you can find airfare + accommodation deals, which can be worthwhile to consider. If you are travelling from Europe within Europe for instance, you can get some great weekend getaways that are flight/train + hotel for cheaper than booking them separately.

Also consider looking for blogs/Facebook groups/etc. that showcase deals from your local airport (i.e. YVR deals).

PRO TIP: When searching travel sites for flights and hotels, it's best to do it in incognito mode. What often happens is the website you're searching will show you one price, then recognize your IP address upon a subsequent visit and raise the price since you are likely further along in the buyer's journey. In other words, they know you are ready to buy, so they raise the price to get more money out of you.

PRO TIP: If you are thinking of visiting multiple places, then sometimes it’s cheaper to fly to one airport than another from your home. For example, say you want to go to Paris but there’s cheap flights to London, you can fly to London instead and just take a train to Paris.

PRO TIP: If you plan on doing one-way flights to places, switching orders of cities can make a huge difference in flight prices.

6. Look for a convenient hotel

If you want to visit several places, plan out a rough itinerary before booking your hotel. See if it’s better to have one hotel as your base and just do a day trip to the other city/country, or is it better to book a new hotel in each city/country.

Use tripadvisor for advice and prices on hotels. However, if you go to a different site directly, the prices are sometimes cheaper.

7. Look into visas / vaccines / customs

Visas:

BEFORE you book your flight, you must ensure you’ll be able to enter the country. Obtaining a visa can be a lengthy process, often more than one month. If you don’t have a visa, you may not be allowed into the country, and they will put you on the next flight home – at your expense.

Vaccines:

If you need vaccines (not just COVID, there are many others), you also need to account for adequate time. Be aware that it may take several months for some vaccines to reach their maximum effectiveness, so you may need to have it done at least two months before your trip.

8. Research the local customs

As a general practice, it’s always good to know a little about the local customs. You can research online, or buy a book that tells you everything travellers need to know. You never want to be inadvertently be rude or offensive when you visit a particular country. 

  • In Buddhist countries, it’s considered rude to point with your feet. 
  • In Japan, it’s considered rude to tip your waiter, and stick your chopsticks straight up in your rice. 
  • In Thailand it’s considered offensive for women to show too much skin in temples.

Also, if you could learn a few phrases in the local language, it will go a long way. Phrases such as: ‘please’, ‘thank you’, ‘where’s the bathroom?’, ‘how much?’, ‘yes/no’, ‘I need help’, etc. are common phrases. 

A lot of cultures want to see you at least make an effort to speak their language. Once they see this, they are usually a lot more willing to help you out.

9. Look at things to do, including where to eat lunch and dinner

While it’s not necessary to do every bit of research before you book your trip, you should have a general idea of what you want to do. Once you’ve booked your trip, you can delve back into the research.

If you go to a new city, check if there’s a free tour you can join that will give you an intro to the city. If you would rather have a private guide take you around, this can be arranged as well. It costs more, but they can be well worth the money. Guides can often get you better rates, translate for you, negotiate for you, educate you on the sites, find bathrooms when needed… and you will be travelling around in an air-conditioned vehicle all day and don’t have to worry about transit.

Know what you want to do:

  • If you have an idea of what you would like to do on your trip, then it makes it a little easier to plan. Just figure out where those activities are located, and plan a route that is convenient and efficient.

Don’t know what you want to do:

  • If you have no idea what activities are available, then you can do some quick research to see what there is to see and do (forums and travel blogs are good for this). Keep in mind where those activities are located since you’ll need to plan a route that is convenient and efficient.

PRO TIP: If you have just a few days in a city, you can google “(#) days in ____ (city you’re visiting)” and see what comes up. There are lots of guides available online and checking out a few of them can give you an idea of what some of the top sights are.

10. Look at transit / transportation

Renting a car:

If activities, shops, and restaurants are really spread out, and public transit is too complicated or inconvenient, it may be best to rent a car. It’ll cost you more, but then you’ll have a lot more flexibility and convenience, especially in terms of what hotel you want to pick. Often these car rental places are located at the airport.

Public transit:

If you opt for a cheaper hotel that’s further away from everything, at least ensure there are places nearby to eat, convenience shops, and it’s close to transit with easy/fast connections to the sights you want to see.

PRO TIP:
If a lot of attractions are near the city centre and you can walk to a lot of them, then when you look at the hotel, you have to take into account how much you save from staying further away vs how much more you would spend in transit costs (or parking costs if you’re driving), not to mention your convenience.

11. Booking the trip

Before you book your trip, you want to go through the checklist and ensure everything has been thoroughly researched and considered

PRO TIP:

You’ve likely done a ton of research by now and have everything finalized. What I like to do is compile all the notes that are relevant to the trip printed and assembled into a brass-fastener folder.

You can have everything you need from activities, restaurants, pre-booked tickets, maps, foreign language cheat sheet, copies of passports and credit cards… As you progress through your trip, you can remove (tear out) the pages and discard them, leaving only the pages needed for the remaining days.