Planning: A vacation

I’ve been fortunate enough to do different kinds of travels in my life; from camping in the woods, to discovering the wonders of Italy. I’ve had to prepare many itineraries, and having organization OCD, I figured I’d share with you my tips on how to carefully plan your next vacation.

This may or may not work for everyone of you, but I believe that they are pretty good guidelines.  

The first thing that I look at, even before I start planning, is my budget. How much can I afford to spend and how much do I already have saved up? Whether you’re on a low, medium or high budget, you need to set yourself a limit. The budget will more often than not determine what kind of trip you can afford to take. If you’re already set on a specific type of vacation, budget what you have and what you’ll need to save up.

Ensure that your budget plans for transportation, accommodation, food, activities and souvenirs.

Seriously guys, I know how tempting it is to just throw everything in the air and take off, but it’s so important to have money in case you get yourself into trouble

Who is coming along?
Ensure that you plan your budget according to the amount of people are coming with you, especially if you’re paying for a significant other or family. Are you going in a large group or are you going with one or two people?  (Tip: if you’re going in a large group [10+] ensure you research group pricing for activities, accommodations, and transportation.)

Different groups of travelers include:
        Solo trip
        With significant other
        Trip with friends (up to 5)
        Trip with friends (5-10)
        Group trip (10+)
        Family (including kids) 

How long do you want to go?
Once my budget is completed, I need to know exactly how much time off I can get from work. Do I only get a weekend, a week or 3 weeks? The budget will also be able to help me figure out the amount of time I can be on vacation before running out. For example, I tend to give myself a 150$/day budget. So if I can only afford 500$ for a vacation, I know that I can only be gone for 3 days. 

I know that my 150/day is quite high for some, but with this economy, I think it’s quite appropriate. I could do 75-100/day as well, but I like to have some extra just in case. Granted there are great 1 week vacation packages for 500$ that include transportation, food and accommodations, but still be mindful.

Here are the time tendencies:
Weekend getaway: 1-3 days (perfect for camping/cottage trips)
Adventure getaway: 4-6 days (perfect for visiting a new city)
Relaxation getaway: 7-10 days (perfect for a sun vacation)
Exploring getaway: 11 days + (perfect for exploring a new country and their culture) 

What type of vacation is it?
Now that you’ve determined your budget and the amount of time you can be on vacation, you can determine what type of vacation you’d like to take.
Will you be staying in town and visit local attractions? Will you be camping by a lake, or go to a friend’s cottage? Will you decide to visit a new city a few hours away? Will you be soaking up the sun down south? Or will you be exploring different cultures in a faraway land?

The different types of vacation are really what I enjoy most about travelling.

Mont-Tremblant, QC, Canada – weekend
They have beautiful condos that they rent out to skiers in the winter, this is the view from one of them.


Lima, Peru -15 days
City shot. I have family in Peru and was fortunate enough to have visited them during my Christmas break in 2010

Sol Cayo Coco Resort, Cuba – 7 days
It doesn’t look like a fancy resort, but I loved every minute of this quiet resort in 2012. For the record, Cuban beaches are heaven. 

Florence, Italy – 10 days
Although this is only one city out of three I visited in Italy, this is my favourite. View from my hostel.

Mayo, QC, Canada – 2 days
I love camping. I’ve done it since I was a baby, and know how to set up a tent in 25 minutes, tarps and all. Yes, there are loads of bugs, and dirt…I still love it though. 

How are you getting there?

It’s pretty clear that when you decide what kind of vacation it is, you’ll know what kind of transport you’re taking, but if you’re on a tight budget, do research different options if you can. For example, going from Toronto to New York City; will you drive, fly or bus there?

Different types of transportation to consider:

What type of temperature is it?
Make sure you research the climate of your destination before packing. You’ll want to be efficient and pack accordingly.

What items to bring?  
When I travel I love to bring things to occupy myself.
On the road: I always make sure that my iPod is fully charged, I’ve got a small pillow (if I’m not driving), some healthy snacks and a full tank of gas.  If you’re travelling a far distance, plan ahead and select a few stops along the way to rest or stretch your legs. For example, during a 5 hour car ride, I like to make a stop half way. For anything more than 8 hours, I plan to stay the night at a hotel or with some friends to rest. Driving when tired is extremely dangerous for you and those on the road with you. 
Side tip: If I’m travelling with 2 or more people that have their full license, I tend to schedule a rotation for long road trips. The front seats are designated for the driver and someone who will stay awake with him/her and the back seats are meant for relaxing and taking a nap. At the next rest stop, we switch positions counter clock wise; driver goes to the back, passenger seat becomes the driver and so on.
On the plane: Depending on how long the plane ride is, there is most likely a TV in front of you with a selection of movies and TV shows. I still make sure I’ve got my iPod fully charged, and some healthy snacks (double check what you can bring on board and that it’s sealed) I also like to bring myself light reading like a summer novel or some magazines. Depending on the flight time, I may also take a Gravol right before embarking so I sleep through most of the ride.

On the train: The extra item that I’ll bring with me on a train ride is my laptop and some DVDs because their Wi-Fi doesn’t always work, and the movie selection is quite low.

General luggage: I’ve packed suitcases since I’m 5 years old. Different circumstances in my life made that I needed to travel weekly and so I’ve come up with tips and tricks that I will posting next week. But I do like to limit myself to a certain number of bags depending on how I’m travelling (I also check the train, bus and plane baggage restrictions) — see the post on Packing a Suitcase here.

Other research
If you’re travelling to another country, make sure you research the culture, language, laws and areas where you can get medical services. This will reduce your chances of getting yourself into trouble, especially if this is your first time visiting. 

Do you have other ways to plan a vacation? Tips or suggestions are always welcome! Please feel free to contact us at or leave a comment below! 


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