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How To Plan Your Next Epic Vacation

Travel. It’s one of the single most enjoyable experiences one can have. At least, that’s how we feel at Pin Warriors. From the moment we met, Steve and I agreed that travel MUST be a regular part of our lives – well, that’s what I decided and Steve mostly lovingly complied. Starting with our incredible luna di miele in gorgeous Italy to our babymoon roaming the Emerald Isle, our lives have been so enriched by these experiences that we are confident this is only just the beginning of our mutual love affair with travel.’

One of the things that I find the most exciting about travel is the planning and preparation beforehand. I know, I’m a bit of a weirdo, but as a teacher, it’s kind of in my wheelhouse. I have a passion for budget-friendly travel without the pressure of having to pinch pennies at every stop. After all, as a Pin Warrior, I feel very strongly about DIY-ing wherever I can, as well as taking advice from and testing out recommendations from other pinners.

If you’re planning an epic vacation of your own in the near future, one of the best ways you can prepare for and get the most out of your adventure is to create an account/profile with some of the most reliable and reasonable travel companies. Steve and I absolutely LOVE Airbnb for accommodations and even for some unique experiences that we couldn’t have found any other place. Airbnb now offers an unprecedented number of options to make your vacation one you won’t soon forget, and to help you stay on budget.

An added perk with Airbnb is that you can communicate with locals who are happy to share their favourite spots with you, valuable travel advice, and are generally willing to go above and beyond what you would typically experience with any upscale hotel. In our experience, all of our Airbnb accommodations have far outshone any of the hotels we’ve stayed in anywhere in Canada, Italy and Ireland.

So, without further ado, here are some Pin Warrior tips and tricks to help you plan your next epic vacation.

Communication is KEY

Communicate with your travel partner to figure out where you want to go, what time of year you’re both available, and what time of year best suits the travel experience you both wish to have. Discuss things like how you both prefer to get around while travelling, what route you might want to take, what type of accommodations you prefer, as well as any other things you might want to consider (E.g. accessibility, amenities, excursions, etc.)

Decide on a Budget – and Stick to it!

One of the most effective things Steve and I do while we are planning a vacation, is to create and follow a savings plan that aligns with the vision and expectations we have for our upcoming journey. You can check out our tried and tested savings plan HERE.

Be prepared to account for things like flight, accommodations, transportation, excursions, meals, souvenirs, and anything else you might need/enjoy in preparation for or during your travels.

It is important you stick to your budget at all times as to eliminate any undue stress along the way. Vacationing is intended to eliminate stress from your life, not induce it. You want to be able to enjoy every minute of your time away, so decide on a budget and stick to it.

Begin Exploring your Options

Now that you have decided on a budget, you want to start exploring your options. Do you have any travel perks available to you? Hint: think of any memberships you might have (CAA, Costco), credit card points (TD Travel Visa), work perk affiliations (Edvantage). Do you have any favourite travel bloggers or friends that have travelled to the same destination you’re travelling to? Pick their brains for any and all recommendations.

Planning can seem much less daunting when you can get advice from people who have actually been to the destination you’re travelling to. Research and learn as much information as possible about the places you wish to visit to give you the peace of mind needed to make the most of your time.

Tip: Look at the itineraries professional group travel companies offer. In many instances, you can follow a similar itinerary, but save a substantial amount of money by booking the accommodations and excursions yourself.

Ask Questions to Know What You’re Getting

Once you know the options available to you, you can begin reaching out to the people and the companies that can help you plan your vacation. Begin creating “favourites lists” on Airbnb and start communicating with the hosts of your favourite accommodations to see if their space is what you are looking for, and to find out how you can make the most of your stay with them.

Don’t be afraid to ask questions. Asking questions will not only help to ease your mind about your travels, but it will also help you become more aware of the options available to you. Whenever I am choosing our accommodations, I always contact a few hosts and ask them a bit about their space and places nearby they would recommend. How the host responds to your questions will really give you a sense about whether or not that space is a good fit.

When working within a budget, it is important to compare prices. There are many websites, like, that allow you to compare the prices of different car rental companies and airlines so you can make an informed and reasonable decision on transportation. If you are renting a car, make sure you are aware of any hidden fees up front. Make yourself aware of the rules of the road and common road conditions for the places you are visiting. For example, when driving in Alberta, Canada, windshield damage is very common. If you know this ahead of time, you might choose to get extra rock protection on your rental vehicle. You don’t want any unexpected fees to surprise you while you’re on vacation, so make sure you know what you’re getting and what you can expect before you make any lasting decisions.

Tip: Some countries require you have an international driver’s license. You can get these at any CAA location. Also, don’t forget to contact your insurance company to make sure you have coverage while driving in another country.

Create an Itinerary

Now that you know what options are available to you, it is time to create your itinerary. This should include the places you will be stopping on your journey, how long you plan on staying in each place, and how you plan on getting to and from these places. We always create an itinerary like this one so we’re able to plan accordingly. Knowing these things will be extremely helpful when you begin booking your flights, accommodations, and car/transportation.

[Want your own FREE printable copy of this blank itinerary? Just CLICK HERE and sign up for our newsletter, and we’ll send it to you free!]


If you’re like Steve and me, a guided excursion can be one of the best ways to learn about your surroundings and visit the most popular sights along the way without having to worry about transportation and parking. Follow your itinerary and explore any excursions options available. Steve and I have had great success booking our most popular excursions through Alternatively, Airbnb now offers a variety of “experiences” which are super fun, reliable, and unique to each destination city.

Make Your Vacation Official and Book

No explanation necessary.

Tip: Get more travel points if you use a travel Visa Card to book your trip. If you are booking your vacation well in advance, be sure to make yourself familiar with any cancellation policies. You don’t want to lose money if any extenuating circumstances happen to arise.

Keep the Lines of Communication Open

As you get closer to your departure date, follow-up with your Airbnb hosts to make sure everything will be set up for your arrival. This is also a good time to find out even more about the area you will be staying in. Most hosts are more than happy to share their knowledge and suggestions with you before you arrive so you can plan accordingly. In addition, we have found many Airbnb hosts to be super accommodating with regards to check-in times. If you know that your flight will be getting in well before your scheduled check-in time, there’s no harm in asking your host if they’d be willing to accommodate.

Tip: In case of any unexpected complications, be sure to exchange phone numbers with your host in case you lose your wifi connection along the way and need to contact them.

aAny travel planning tips or tricks you’d like to share? Let us know in the comments, and share the pic below on Pinterest!



2 thoughts on “How To Plan Your Next Epic Vacation”

    1. HI Cindy, thank you so much for checking out our blog! Good luck planning your own epic vacations! Keep us posted…we’d love to hear all about your travels.

      Cheers and best wishes,
      Amanda & Steve

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