How to Plan a Vacation in Just 18 Easy Steps | 2020 Vacation Planning Guide

How to Plan a Vacation in Just 18 Easy Steps | 2020 Vacation Planning Guide

I know vacation planning is overwhelming, but by the end of this post, you’ll be a pro. Here’s how to plan a vacation in just 18 easy (really) steps!

Let’s get started!

So you’ve decided you want to travel somewhere you’ve never been. That’s awesome! 

I speak from experience when I say visiting a place you’ve never been to when you’ve only just started traveling can be… overwhelming to plan. And that’s putting it mildly.

My first trip outside the continent was to Paris. And every time I tried to put something together, the sheer vastness of information out there just shut my brain down. So I barely cobbled together a borderline sarcastic itinerary, and called it good.

The Louvre, Paris | Broke Girl Abroad
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Not for nothing, I had a great time in Paris. But far removed, I can see why I checked out of the planning process. Cause… where do you even begin?

That’s what I hope to answer here. This post is meant to be a guideline for the next big vacation of yours. It’ll walk you through from start to finish, and when all is said and done, you’ll have put together the perfect trip.

This is a long read, so let’s dig on in!

Disclosure: Some of the links in this post are affiliate links, meaning at no additional cost you, I will earn a commission if you click and make a purchase. As always, my recommendations are based on my own experiences and I am very grateful for your support. Thank you!

How to Plan a Vacation in Just 18 Easy Steps

Pin this checklist for later!

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1. Find out where you want to go, based off of interests

I recommend Pinterest for this, funny enough. It’s a great way to get a visual of your potential destination. So let’s say, for example, that you really love castles. And on your big vacation, you’d love nothing more than exploring some super old castles. Neat! Let’s type in “castles travel” into Pinterest and see what comes up.

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Ireland’s looking pretty nice. Let’s go there.

2. Figure out the best time to go

For this, research the shoulder season and see if you can align it with a holiday to maximize your time off.

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If we search “Ireland travel shoulder season,” we see that May looks like a good time. Check out the weather averages too. Is this something you’d be cool with? If so, let’s aim for May, and see if we can line things up with Memorial Day weekend.

3. Plan the amount of days you’d like to spend there

You know yourself best here. What would you feel is enough time to explore a new place, recharge and put those vacation days to good use?

I earn one day per year, and would be sitting at 6 days before the trip. So I would probably aim to stack my weekends and spend 10 days in Ireland. Sounds lovely to me.

4. Sign up for Scott’s Cheap Flights and keep your eyes peeled

Not an affiliate, just a fan. The subscription will cost you $59, and it won’t take you long to find a deal that will more than pay for it. Even if you live near a nightmare midwest airport like me (hi, MCI), Scott and his team will find you something. You’ll want to look for subject lines like these:

Scott's Cheap Flights
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There’s usually a limited time window, but you already know when you want to go and for how long, so no sweat! Time to book those flights.

5. Figure out what you’d like to do

Now we have our flight booked, and the trip is starting to feel real. Isn’t it exciting?! Now it’s time to get a bit of an idea towards what you’d like to do. We won’t need to plan everything down to the millisecond, this is just an overview.

Let’s start searching again. Try “best castles to visit in Ireland.”

How to Plan a Vacation in Just 18 Easy Steps | Broke Girl Abroad
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Do any immediately stick out to you? I’m a bit partial to the Blarney Castle, it’s legend for a reason, after all. So let’s open up a document (I use Google Sheets) and start listing our ideas. 

How to Plan a Vacation in Just 18 Easy Steps | Broke Girl Abroad
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Blarney Castle, what else? Well, what appeals to you? Do you like abandoned castles in the middle of nowhere? Or how about one overlooking the ocean, or stunning scenery? Or maybe one that’s been preserved and restored to how it would’ve been in its prime. The last one is more my scene, and it looks like Dublin Castle fits the bill. So we can add that to the list as well. Here’s where you can kind of play around, and pick a couple of big-ticket items you won’t want to miss

6. Find out what’s popular

You’ll find a zillion guides telling you what is and is not worth your time. It can get overwhelming. So let’s parcel it down by searching “10 day Ireland itinerary.” That way you won’t hear from people who spent longer/shorter times. I like to start with Rick Steve’s suggestions. 

How to Plan a Vacation in Just 18 Easy Steps | Broke Girl Abroad
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Pretty straightforward. Let’s write those down, and take a look at two more blogs, to get a good comparison.

How to Plan a Vacation in Just 18 Easy Steps | Broke Girl Abroad
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From here, you can start your research.

7. Learn what you’d like to do

For this, I recommend perusing the country’s official tourism website. Most tourism destinations have one, and they’re awesome! A treasure trove of information from the people who know the place the best. Look at how easy they make it.

How to Plan a Vacation in Just 18 Easy Steps | Broke Girl Abroad
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Let’s click on Dublin, since that’s where we’re flying in. Right away we’ve got some fantastic resources at our disposal.

How to Plan a Vacation in Just 18 Easy Steps | Broke Girl Abroad
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Look at their suggested attractions and restaurants. What do you think? Anything stand out? Make a list for each destination. Don’t worry about when and where just yet. For now, write down what looks fun.

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8. Determine the best times to do what you’d like

Here is where Google Maps is your friend. Let’s continue with Dublin. I would love to visit the Book of Kells, so let’s search that and see where it is.

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Take note of the address and hours of operation. Looks like it’s open all week, which is nice. This can be a flexible itinerary item. 

Continue to do this for each item on your list. The destination and operating hours will help you plan out your time in Dublin. For example, I can see that the Little Museum of Ireland is an 8 minute walk away from the Book of Kells, and opens an hour later. So ideally, I’d visit the Book of Kells first, and the Little Museum afterward. You catch my drift?

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This will also determine your schedule. Are you a person who can spend hours in a museum? Or are you there to see a few big pieces and bounce? Stuff like that. If you’re not sure, it’s time to start being a tourist in your own city. I live in Kansas City, and after a few trips to the Nelson-Atkins, I learned my happy place with museums is about two hours, give or take.

9. Book your hostels

So now your itinerary has really shaped up. You’ve figured out that you’d like 5 days in Dublin, with two day trips in between, 3 days for Cork, Dingle and the Ring of Kerry, and 2 days in Galway with a day trip to the Aran Islands. I love it!

Now it’s time to book your hostels, and I’m going to return to Google Maps for this, because they make it so easy. Go to Dublin, and search hostels.

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Boom.

You can even type in your dates into the sidebar and get an idea for what you’re likely to pay. 

How to Plan a Vacation in Just 18 Easy Steps | Broke Girl Abroad
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Now it comes down to your budget, the location and the reviews. I tend to trust Google reviews more than anything. They’re brutally honest. Scroll through a few and see what the hostel is rated on. Does it all look legit? Is it a good location for you? Something you can afford?

Then let’s book it!

Side note: I love staying in hostels, and recommend them to all. You don’t have to stay in a 10-bed room if you don’t want. For extra cash, you can usually upgrade to a private room with an ensuite, still for way less than a hotel.

10. Figure out your transportation method

You’ll be traveling to quite a few cities with some day trips in between. So now it’s time to decide… would you rather drive or not? No judgement either way.

If you do decide to rent a car, always get insurance. Even the best of drivers find new locations a bit disorienting, especially with Ireland’s narrow, wavy roads.

If driving isn’t for you (raises hand) then start searching for other options. I’m a big fan of OMIO, as it can show you the bus, train and flight paths from anywhere in Europe. You could also check sites like Viator and Get Your Guide, to see what kind of day trip offerings appeal to you.

11. Get travel insurance

Hear me out. The one time I didn’t get travel insurance, my flight got delayed. Departing and returning. I missed an entire day and had to do a bizarre work around with my schedule and get ahold of my hostels to let them know that I’d be a day late. If I had gotten insurance, I would’ve been reimbursed for that. I got stuck in Toronto on both occasions, and while I appreciate the city, it’s an expensive place to be stuck in. Twice. In the same two weeks.

Don’t be like me. See what insurance company fits you best, and get a plan.

12. Book your tours and tickets

Since you know what your activities are gonna look like, start looking into booking the tickets, especially if there are skip-the-line options. What I do is print out a paper copy, and save a digital copy to Google Drive, and set it so I can access the file offline. That way, you’re prepared no matter what.

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Find out if there’s a special tourist card available. These can be hit or miss in terms of savings (does Paris really think you’ll hit up that many places in 48 hours?) but sometimes it can be a real cost saver. A cursory search shows us that Dublin offers one, and it even comes with suggested itinerary! Of course, if only half of what’s offered interests you, don’t bother. Just book separately. But if you’re jumping for joy at all the offerings, give it a go.

13. Figure out what you want to pack

I’m definitely guilty of being this type of person:

That said, just use your own best judgement here. Past forecast averages in Ireland tend to hover between 50 and 70°F in May. Wear what makes you comfortable. Keep in mind, you’ll be walking a lot (and it’ll probably rain) so pack clothing that’s friendly for an active traveler.

Oh, and always bring more socks and underwear than you think you’ll need. That saved me when I got stuck in Toronto.

14. Double check your passport

Always a good idea to make sure it’s up to date so you’re able to… you know, actually go on your intended trip.

Passport
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15. Have your credit card all set up

Foreign transaction fees are the worst. Avoid them if you can. 

All that aside, it might be time to see if you’re due for a credit card upgrade so you can start accumulating points. NerdWallet has a comprehensive guide to the best travel credit cards. And, a quick side note, make sure your bank knows when you’ll be out and about. Nothing ruins a vacation faster than fraud detection prohibiting any of your payments abroad.

16. Get your budget in order

Look through restaurants, bars, popular shops and the like, and determine what you’re comfortable spending while you’re in the country. While booking the flight and accommodations definitely takes up most of the travel budget, you’d be surprised by how quickly your spending can add up once you’re actually on vacation.

Galleria Vittorio Emanuele II, Milan | Broke Girl Abroad
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So now’s the time to ask yourself what’s important. Are you a huge wino who’s willing to forgo souvenir shopping if it means you can squeeze in a wine tasting? Or are you a dessert fiend who will eat simple meals in the name of sampling several epic sweets? Decide for yourself, plan an amount to spend, and stick to it.

17. Download apps and make sure your phone is ready to go

Google Maps will track your location offline, so no need to worry about getting lost. When you’re at your hostel, use their WiFi to plan your route, and then Google will take over.

Viber is an awesome app I used while I was abroad to call home. All you need is, again, solid WiFi.

It’s also worth looking into any country or city-specific apps. Those are pretty cool and full of good info.

Also, take a look at your phone plan. If you have T-Mobile, you won’t get hit with fees as long as you’re diligent about only using your phone when you’ve got WiFi. Other carriers typically charge a daily fee. You can bypass this, however, by picking up a SIM card at the airport and buying data upfront.

18. Get excited!

Self explanatory. I hope you have the best time ever on your vacation and got some great tips for planning your next one!

Did this guide help you plan your next trip? Let me know in the comments!

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Pin me!

Safe travels!

-Maggie

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12 Responses

  1. Great tips! I remember when I planned my first international trip I was so concerned so I went all out and read everything possible. It can really get overwhelming planning your first few ones.

  2. Fabulous tips! So well organized and helpful. I’m a visual learner so recording ideas down and creating Pinterest boards (something I am new to!) is incredibly useful. Pinning this!

  3. This is an awesome all-encompassing guide for hopeful travellers looking to plan a trip. Love the organisation and detail 😀

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Maggie, the Broke Girl Abroad, is just another Millennial who wanted to make a travel blog because of that one time she studied abroad.

Now a 9-to-5 employee, follow along as she attempts to see the world by balancing her budget, her 40 hour work week, and her precious, precious vacation days. 

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