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ULTIMATE TIPS FOR PLANNING AND BOOKING TRAVEL LIKE A PRO! | Published December 9th, 2020 | Last Updated December 28th, 2020

Itinerary, camera and travel budget sitting atop a vintage map

For all you “fly by the seat of your pants” and “go with the flows” that plop yourself down in a destination and figure out what to do once you’re there, you might want to look away, this article describes planning a trip in great detail! For the rest of us, who are consummate planners and enjoy the whole experience of it, this article is for you.

There’s an art to planning and booking a trip, from getting the best deals and figuring out which sites you’ll visit to avoiding line-ups at museums and booking tours. It starts with breaking down your planning into steps. Trying to figure out where to go, what to see, and how to book, all at once is overwhelming. If you start at the beginning and follow these steps, it makes your planning less complicated.

Table of Contents


1. Find your Inspiration

2. What Attractions Will you See?

3. Mapping Your Trip

4. Deciding on Transportation

5. How Long will you Stay?

6. Booking Accommodations

7. Booking Flights

8. Booking Tickets and Tours

Find yourInspiration

STEP 1 - You’re at the first step in planning your journey but haven’t the foggiest where you’ll even go. It can be daunting; the world is a big place, after all.

You can find great inspiration for your travels by:

  • Word of mouth from friends and family that have travelled somewhere they loved

  • Travel books

  • Websites of other travellers. Look through photos and information of places they've visited and see if a destination grabs your attention

  • Internet Searches

Snow-capped mountains reflected in the water along Icefield's Parkway, Alberta

Driving along the Icefields Parkway in Alberta, Canada

Let's focus on Internet searches for a moment. Since people are often limited to specific times when they can travel, it makes sense to figure out what country is best to see during that period of time. A great place to start is to search “Best Countries to Visit in ______” and fill in the month of the year you'll be taking your trip. If the time of year isn't an issue, then searching phrases such as “Must-see travel destinations 2020” and “Underrated Travel Destinations” are also great options.

Whatever you decide, realize that the time of year you choose will significantly impact both price and weather.

What is the Best Season for Travel?

  • High season - you can expect higher prices, typically higher temperatures and more tourists as well. For many with children on school breaks it may be the only option.

  • Low season - you’ll be blessed with lower prices, but you may also be encountering inclement weather that may not allow you to see all the sights you had planned. The fewest tourists will travel at this time as well.

  • Shoulder season - A personal favourite! Prices have started to come down, streets jammed with other tourists are dissipating, and the weather is sometimes as good as, if not better than high season; think warm breezes instead of sweltering heat.

What Attractions will you See?

STEP 2 - ONCE YOU HAVE YOUR COUNTRY OR CITY CHOSEN, NEXT, YOU NEED TO FIGURE OUT WHAT TO SEE - There are specific sites I rely on when deciding what to see and do on a trip, which mostly include Trip Advisor, Pinterest and Google searches.

  1. Start by doing an Internet search of “must-see Austria” or “must-see cities in Austria.” A list of locations or attractions will come up with photos giving you a general idea of all the ‘can’t miss’ sites. Scroll through these photos and descriptions to see what interests you.

  2. You can also use Trip Advisor using the same searches

  3. Use sites of the people you follow. Look at their photos and read a few blog posts about their experiences in that destination.

  4. If you like off the beaten track destinations, use this in the search engine for the country you're researching. “Off the beaten track Austria.”

  5. Hop over to Pinterest, which also has an abundance of photos and information on what to see and do in just about any city.

From this information, make a list. Jot down the points of interest and locations that appeal to you.

Mapping your Trip

STEP 3 - FOR THIS NEXT STEP, I RELY SOLEY ON GOOGLE MY MAPS - It’s super easy and highly effective for visualizing what you'll see. I create a few maps for each destination.

One is the country overview map, which shows me where each city is located, and the other maps are the sites I want to see in each city. Here is a sample country overview map created for our Austria example and a sample of the places to visit while in Vienna:

Vienna, Austria Itinerary map created in Google My Map

Maps Like These will Make Trip Planning Easier when Booking Hotels and Creating Itineraries

How to Create Your Own Google Map - There are several features to Google My Maps, but this information tells you how to create a very basic map with only one layer. (You'll need to have a Gmail account to create a Google My Map. If you don't have one or don't want a Gmail account, maybe look into other online map-making sites).

1. Start by doing an internet search of ‘Google My Maps’ Sign in and click 'Create a new map'

2. Click the top left corner that says 'Untitled Map' and type in a name.

3. Next, in the search bar at the top, enter a location or point of interest.

4. When the green pin drops on the map, click on 'add to map'

5. In the box that comes up, there are a few options for editing.

  • The paint bucket changes the pin style and colour.

  • The pencil allows for text and descriptions to be entered.

  • The camera adds images or videos.

  • The arrow allows you to get directions from one point to the next.

Add your points of interest one by one. Once these points are on the map, look at the travel path you've made. You'll use this to figure out the next steps of transportation and length of stay.

Deciding on your Transportation

STEP 4 - HOW WILL YOU GET FROM ONE LOCATION TO THE NEXT? You’ll need to figure out how you’re getting from point A to B to C and so on. Here are some options to consider:

  1. Self Drive - Are you comfortable driving in a foreign country? If the answer is yes. Do some research on whether the place you’ve chosen is a safe place for foreign travellers to hit the road. While you may be ready to slide behind the wheel in Vietnam, the chaos on the streets of a place like Ho Chi Min City may leave you reeling.

  2. Public Transportation - Maybe the train or bus would be a better option. Check out their routes to see which would be the best mode of transportation to get from one destination to another.

  3. Tour Company - This could mean joining a large group on a bus or hiring a personal driver for the day. If there are a few points of interest just outside the city you're staying in, try searching tour companies like Viator for Day trips from that city.

Blue seats with tray tables in an empty train interior

Figure Out the Best Mode of Transportation and Book in Advance if the Price is Right

How Long will you Stay?

STEP 5 - HOW MANY DAYS WILL YOU NEED IN EACH LOCATION? - I rely heavily on Trip Advisor and travel books to answer this question, but I also look at the maps I've created.

  • Once I have my Google Country overview map, I also map what to see in each city. I use different coloured pins on the city maps to represent what I will see on different days; for example, green pins will be day one in the city, orange pins represent day two, and so on. (See the Vienna Google My Map above).

  • IMPORTANT TIP: Be sure to figure out the amount of time it will take to get from one destination to the next by the mode of transportation you've chosen. If it’s an eight-hour train ride during the middle of the day, you'll be stuck missing some of the locations you wanted to visit unless you include that time in your planning.

  • BEFORE MOVING ON TO BOOKING: Before I book a single hotel or flight, I jot down the general itinerary like the one in the sample below, including times it will take to drive or take transit from one location to the next.

Sample Austria Itinerary

May 13th - Flight from Toronto to Vienna, Austria

May 14th - Land in Austria in the AM - stay in Vienna

May 15th - Stay in Vienna

May 16th - Stay in Vienna

May 17th - Stay in Vienna

May 18th - Explore Vienna (AM), drive to Graz @ 5pm (2-hour drive) - Stay in Graz

May 19th - Stay in Graz

May 20th - Drive from Graz to Hallstatt @ 9am (2 hours) - Stay in Hallstatt

May 21st - Stay in Hallstatt

May 22nd - Drive to Salzburg @ 6pm (1 1/2 hours) - Stay in Salzburg

May 23rd - Stay in Salzburg

May 24th - Stay in Salzburg

May 25th - Stay in Salzburg

May 26th - Flight Home (AM)

Booking Accommodations

STEP 6 - BOOK YOUR ACCOMMODATIONS - Now that I have the number of days I'll need in each city from the itinerary above, I can start booking hotels. I'm going to come clean right from the get-go and say I'm addicted to I’m not even sure that’s something to be addicted to, but I digress. I started using this website when planning my first solo travels back in 2009 and have since booked 74 stays through the site.

To get the best deals, you can wait until you arrive in a city, which means you may or may not luck out with the prices, and you may or may not have an option of the accommodations you'll be booking. The idea of this puts my organized self into a tailspin, but everyone has their way of travel planning. I prefer to book far in advance (generally 6 - 9 months) to get the best selection of hotels and the best selection of rooms on If you've never used the website before, you may like the post: 10 Reasons I Rely on for Booking Accommodations.

Hotel room desk with coffee station, lamp, laptop and phone

You'll Get the Best Selection when Booking Accommodations in Advance

Booking Flights

STEP 7 - SEARCH FLIGHT PRICES AND BOOK - I use sites like Skyscanner and Flighthub to give me an idea of the availability of flights and the cost. If it’s more expensive to take this trip in the last two weeks of May, why not try for the first two weeks to get a better deal?

In Canada, Skyscanner suggests that you book one month in advance to get the best deals on both international and domestic flights. Algorithms that determine pricing also indicate that the best day to book a Domestic flight is Sunday, while you're more likely to get a better deal if you book an International flight from Canada on a Thursday.

Top down view of an airplane on a runway getting ready for flight

In Canada, Book Flights One Month in Advance to get the Best Prices on International & Domestic Flights

Booking Tickets and Tours

STEP 8 - BOOK ATTRACTION TICKETS AND TOURS ONLINE TO AVOID QUEUES - I would only suggest doing this for tours that may sell out or for attractions that have notoriously long lines, because who wants to be tied to a schedule of pre-booked entry times on vacation?

Early on in my travel days someone gave me this advice and I saw the benefit of it right away. I found out before visiting Sagrada Familia church in Barcelona that the queues were incredibly long and the wait times were averaging an hour or more. I pre-booked my entry through their website, walked up to the ticket holders entrance, and right past hundreds of people waiting in line. The same situation happened at the Uffizzi Gallery in Florence, I walked right in.

Here are some pointers so you can book ahead but not be tied to a schedule:

1. Find out which sites are known to have long queues. Book an online ticket for those attractions only. After all, who wants to be strictly tied to a schedule for every attraction you plan to visit. I find there may be one or two in each city that requires some pre-booking and sometimes none at all.

2. Why not book an attraction for first thing in the morning? When you're done you have the rest of the day to be schedule-free instead of waiting around for an entry time in the middle of the afternoon.

3. Sometimes, you save money when you book these tickets online. Spend some time searching for these discounts, especially if your budget is tight.

4. Take advantage of the Passes offered in various cities. They combine some of the best attractions for a set fee. Figure out what you'll see and whether the cost would be greater to buy them separately. Some of these City Passes also offer 'skip the line' deals, which makes them even more beneficial.

I hope this planning guide helps get your trip organized, saves you money, and makes the most out of any vacation you book in the future. Happy planning and happy travels!


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