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11 Steps to Planning a Stress Free Vacation

11 Steps to Planning a Stress Free Vacation

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I’m a massive planner. I always have been. I could literally spend HOURS (Okay, I do literally spend hours) researching the best places to stay, all the things there are to do, how to get around, and even what souvenirs I should buy while I’m there (is that weird?).

Luke and I are headed to Costa Rica for two weeks in July and I can’t wait. I’ve been spending WAY too much time figuring out all of the above and scouring the internet for any and all information that I can (don’t worry, there will be plenty of Costa Rica content once we get back!).

I wanted to share my to-do list with you since I realize not everyone is as Type-A as I am and planning isn’t everyone’s forte. This is the exact process I have used to plan our two-week trip and is the process I’ve been using basically for the last year or so whenever we’ve gone on a short-term trip somewhere in Mexico or the US.

1. Book Flights

This is the first thing that I do. I’m not exactly great at planning ahead for trips, so I usually do this 2-3 months before I go on a trip. Unless I’m flying super long distance, like Mexico to somewhere in Europe, I try not to book more than 4 months in advance.

I’m usually pretty flexible with dates, so I go straight onto Skyscanner and select the “entire month” for the destination that I want to go to.


how to plan a short term trip

On the home screen, make sure you select which month you are looking to travel in.


How to plan a short term trip with skyscanner

Once you select “search flights” you’ll be brought to this screen so you can see what the cheapest day to fly is. The ones in green are the cheapest available days.

It’s pretty simple to do and is a great way to ensure that you get the cheapest flights.

If you’re planning further in advance, like 4-5 months in advance, then you can set up an alert on Skyscanner so that they notify you when flight prices drop for a certain destination. Just be ready to take advantage of those price drops because they don’t last for very long.

book flights with skyscanner

Click the button that says “Get Price Alerts” on the left side of the screen once you’ve chosen the dates you want to travel on.

The only thing about Price alerts is that you have to select specific dates – perfect for people that have set vacation days.

skyscanner price alerts

This box will pop up once you select “Get Price Alerts” and you just have to enter your email address. They’ll notify you of any changes in price.

I like booking my flights first because I know exactly how many days I’ll be spending in the country and I can plan everything from there. For me, this is the biggest stress of travel and I like to get it out of the way first so that I know that money has already been spent and I don’t have to keep checking for better prices.

Check flight prices on Skyscanner.

2. Create a Board on Pinterest

I am a serious Pinterest addict and I love creating a new board every time I’m planning a trip (I have 76 boards and counting). It helps keep my organized and allows me to dump any information I find on the internet into one place.

I usually use Pinterest to search for blog posts with itineraries, things to do, travel guides, packing lists, and pretty photos. If I find a website away from Pinterest that has good information about the place I’m traveling to, I’ll pin it to that board manually. 

Using pinterest to plan a trip

3. Make a List

Once I feel like I’ve done enough research on what there is to do and what interests me most, I make a list of all of the places that I want to go to. Depending on the length of the trip, this list will either be really long or totally ridiculously long. I know that I probably won’t have time to go to most of the places on the list, but I’m a pretty visual person, so I like to see them all written down before I realize how unattainable it is.

4. Cross Things off the List

Once I have a list I can focus my research on those specific places. I can price up how much each of the activities will be and whether that’s in my budget or not. I find out if I can get to those places on my own or if I need to go on a tour.

I look at how much the accommodation costs are in those places, how much the food will be, whether there are ATMs there, how I’ll get around one I get there. I don’t like to be totally crazy about it, but I want to have a good idea of how long I might want to spend in each place and whether it’s worth the cost.

bacalar mexico

Daydreaming about all of the beaches I’m going to lay on is a MASSIVE step when planning a trip.

5. Map it Out

When I’m only going somewhere for a short period of time, I want to make the most of my time there. That means bringing up good old Google Maps and figuring out how long it’s going to take to get to each place. I want to know if I’m going to “waste” an entire day getting from one place to the next. When you only have 14 days, I don’t want to spend half of that time on a bus.

This is usually when I figure out exactly what I want to do for my trip and roughly narrow down my itinerary. 

6. Book Accommodation

Anyone that has been following along with my blog for a little while will know that I am basically obsessed with Airbnb (I even wrote an entire post about it). Whenever I’m booking a trip, whether it’s for three days or three months, I start my search on AirBnB.

I also check out reviews from other bloggers about what hotels or hostels they recommend, but in the end, I almost always feel like the value for money is far better over on Airbnb.

If you’ve never used Airbnb before, sign up through this link to get up to $40 off your first trip (I’ll get a discount on my next trip if you use that link, hope you don’t mind!).

how to use airbnb

I always use the filters to check “entire home” and adjust the price to the maximum that I’m willing to pay per night

7. Screen Shot Everything

Just before I leave for my trip, I usually take a screenshot on my phone of my flight details and any hotel details that I’ll need when I arrive. There have been so many times where I am about to arrive in a new country, I’m handed an immigration slip, and I have absolutely no idea what the address is for the place I’m staying. Immigration officers really don’t like when that happens.

It means I don’t have to stress about whether there’s going to be wifi at the airport when I get there. I have it all stored as a photo.

9. Download the Map

I learned about the app several years ago now and it is literally the best travel app I have on my phone. It has navigation capabilities, you can zoom in on streets, and find restaurants in the area, all without needing wifi or data. All you have to do is make sure that you download the map for the region you’re going to before you lose your wifi or data connection. I make sure to do this before I leave home just to make sure.

10. Get Travel Insurance

I am a massive believer in getting travel insurance, even for short trips. I have been using World Nomads for the last seven years for the ease and the price. World Nomads makes it super simple to insure yourself even just a few days before you leave for your trip (you can even buy insurance in the middle of your trip).

One of the biggest reasons I get travel insurance is not only for medical emergencies, but to protect my stuff. Blogging and freelance writing means that I don’t go anywhere without my laptop and camera, so I want to be 100% sure that they’re covered in case anything happens.

11. Buy Last Minute Necessities

If we’re going somewhere hot, I make sure I have enough sunscreen and bug spray. I recently had to get myself a rain jacket so that I could enjoy hiking in Costa Rica during the wet season (I’ll let you know how that goes).

I know those sorts of things will be more expensive in tourist destinations, so I like to make sure I prepare as much as I can to avoid overspending once I get there.

These are just the ways that I’ve learned how to make the most of a short trip somewhere. I know it sounds like I plan everything to a T, but I leave a lot open for the opportunity to change and swap things around. I don’t schedule our time during the days, I just make sure that the major expenses like flights and accommodation are sorted so that we don’t get there wishing we’d planned more.

How do you plan out your vacations and trips to make sure you make the most of your time? Let me know in the comments!

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stress free tips for planning a trip

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Tuesday 27th of June 2017

Great tips! Type-A's unite, haha!

I haven't heard of that maps app before, I'll definitely be checking that out for my next trip :)