How to Plan Your First Trip

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It seems odd that I’ve written a post on how to plan your first trip, but many people have no clue where to begin when it comes to travel. Okay, maybe it’s due to a lack of motivation or laziness, but the idea of this post is to guide you through planning a vacation.

To be fair, planning a trip, especially when other people are involved can be quite intimidating. I obviously can’t do everything for you, but if you follow these steps, you’ll find that it may be a lot easier to plan a trip than you expected.

How to Plan Your First Trip

Pick a destination

For me, planning your first trip starts with your destination. Considering how big the world is, it’s absolutely shocking to me that some people have no idea of where to go. My best suggestion is to pick a place that you have some kind of connection to. Maybe it’s a place where you have friends or family, or perhaps it’s a place you saw in magazine; inspiration can come from anywhere.

The biggest problem you may have is narrowing down your choices. First time travellers tend to have very different ideas in mind. You might lean towards an African safari one second, but after a stressful week at work, you may be looking to relax in Hawaii instead. Settling on where you want to go can be tricky, but sometimes the following steps may help you come to a decision.

Set a budget and start saving

Quite often your budget will determine where you go. Some destinations cost more than others so you need to do some research on costs before deciding where to go. That being said, there are two ways to determine your travel budget.

You can set aside a set amount every month. Let’s say $300. That would give you a yearly travel budget of $3,600. Since you have a yearly budget, you just need to find a destination or destinations that fit within that budget.

The other way to budget is by working backwards. Let’s say you’re estimating your trip to Japan is going to cost you about $4,500. Well that means you need to save $375 a month to stay on budget.

Now that you know your numbers, it’s time to start saving. The easiest way to do so is by simply making travel part of your monthly budget. This way you’re always putting aside money to go away. Alternatively, if possible, you can work more hours which would give you more income.

You’ll also want to consider applying for one of the best travel credit cards in Canada. Since you’ll likely be spending a fair amount of money on your flights and hotels, you might as well earn some points. The signup bonus alone can often help pay for a good chunk of your travels. You may also want to apply for a credit card without foreign transaction fees so you can save out on extra charges.

Book your flights and accommodations

This is the point in your trip planning where you need to start making your bookings. With flights, if you’re flexible with your dates, you can save money. Travelling in the off season is always cheaper than the peak while flying out a Tuesday will usually cost you less than flying on a Friday. There’s no trick to flights, prices go up and down all the time. Instead of spending hours searching for the cheapest airfare, just set up a price alert so you’ll be notified if there are any price changes. I wrote a full guide on how to save money on flights which you can check out now.

With accommodations, it really depends on your budget. Hotels in the best locations will always cost you the most which is why you should always consider your other options. Staying just outside of the main tourist areas will often save you a decent amount, and there’s always Airbnb which is normally cheaper than hotels in the area. Use my Airbnb referral link now to get $50 off your first stay. Read my guide now on how to save money on hotels.

Research what you want to see

Researching what you’ll actually do in the city as also vital to your decision making process. Years ago I went to Shanghai because I thought the city looked cool, but there weren’t that many actual attractions I wanted to see.

Attractions can be anything. From parks to museums to day trips. You don’t need to visit cities that will keep you busy every second, but you want to pick a place that interests you. Note that sometimes food may be the main attraction. There’s nothing wrong with visiting a destination just because you’re interested in their food.

Now that you know what you want to see, and you’ve booked your flights & hotels; now is the time to start buying any attraction passes and online tickets that will save you money. Make sure you’re only buying tickets to things you will see. You might as well start building a rough itinerary now too so you can maximize your time.

Get familiar with the local scene

As the date of your departure date quickly approaches, you should basically be looking up logistical things for your trip. Think the key things such as public transportation. Find out the best routes to get to your accommodations from your hotel as well as the average cost of a taxi in case you’re arriving late.

Getting familiar with public transportation is vital if you want to keep costs down. Start looking at transit maps and figure out what the best transit passes are. You’ll also want to find out what the local customs are when it comes to tipping. In some countries, tipping isn’t required while in others, 25% could be the norm.

Finally, about a week out before your trip, you’ll want to double check all your documents. With things ready to go, look up if there are any events going on such as food festivals or weekend markets. These kind of events are perfect when exploring a new city.

Final word

There’s no set way when you’re trying to figure out how to plan your first trip. But these steps will put you on the right path. Also note that the best laid out plans don’t always work out. Take the time to explore things that you didn’t have scheduled and don’t be afraid to go off the beaten path.

About Barry Choi

Barry Choi is a Toronto-based personal finance and travel expert who frequently makes media appearances. His blog Money We Have is one of Canada’s most trusted sources when it comes to money and travel. You can find him on Twitter:@barrychoi


  1. Laura on June 11, 2019 at 10:30 AM

    Great suggestions! Travel is one of the pkaces I splurge! One more suggested is to start small. Start by planning a long weekend. If you haven’t traveled before start by planning a three or four day vacation rather than two weeks

  2. Sd on June 19, 2019 at 3:29 AM

    Barry, do you find that it’s usually cheaper to exchange currency at the destination that you’re traveling to (not the airport) compared to exchanging it in canada first?

    • Barry Choi on June 19, 2019 at 3:28 PM


      It depends on the country really. Generally speaking, I do find it cheaper to withdraw cash when aborad at ATMs. That being said, if I’m at home and I see the exchange rate is 2.5% or less at the bank or a currency exhcange office, I’ll just change some money there.

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