10 steps to planning the perfect vacation

I’m a weirdo. I LOVE planning vacations and trips. Even if they aren’t my own trips, I absolutely love researching places around the world. In fact, the perfect weekend for me is browsing through Bloglovin’s and Pinterest and planning my next dream vacation (even if that vacation never happens). While travel planning can be very stressful, with this 10-step plan you are sure to have a fantastic adventure.

Step 1: Determine the type of vacation you want

Recently my husband turned 30. I asked him a few months before his birthday where he wanted to go and he said he didn’t care. Wives out there know – don’t listen to a man that says “I don’t know.” If it were up to me we would have had a romantic weekend away in Greece, but I knew that was not what he really wanted. So I rephrased the question: What type of vacation do you want? 

After rephrasing the question he still seemed a bit confused. When thinking about vacation, 4 things to come to mind: 

  • What type of atmosphere do I want on my vacation?
  • What type of food do I want to eat?
  • What type of activities do I want to do?
  • What type of landscape do I want to wake up to every day?

I made a graphic for him and filled in different things that I was also interested in. I asked him to circle something from each column.

How to narrow down where to go on vacation

Okay, now I know that we are going to go on a relaxed beach vacation that has great hiking and walking paths and Tapas style food. Before we can decide where we can go, we have to get to the next step: the all-dreaded budget.

Step 2: Know your budget

I used to be a teacher. I unfortunately know how to scape together the very last set of pennies and budgeting is something I absolutely hate doing. But, in order to travel you must know how much you can spend. I am not very good at knowing how much I spend on every vacation, but I do know what my max is for that trip. For example, we took a spontaneous trip to London for our 4th anniversary this year. I knew I didn’t want to spend more than $500 so made sure that flights + accommodation didn’t exceed $350 so we had enough money to spend on food, drinks, etc. Unfortunately, I did not realize how expensive London was (poor planning) before arriving and one night out to dinner cost about $75. The next day we went to the grocery store and bought lots of snacks to get us through the rest of the trip. This was poor planning on my part and I should have done more research on the destination before booking our ridiculously cheap airline tickets from Ireland.

Once you know how much you can spend, as you start to research potential destinations think about the big-ticket items:

  • Airline tickets
  • Accommodation
  • Car hire and/or public transit
  • Food/Drinks
  • Tours/excursions

Now that you have those items in mind, time for the fun part!

Step 3: Macro-Research (Big Picture)

In step 1, we decided what type of vacation my hubby wanted for his special day. I know our budget thanks to step 2. Now, where can we go? I go to two different websites to start figuring out where we can go.


Kayak Explore (for the Americans)

You can put in your airport, the month you are interested in, and your airline budget and the map will produce all of the different places you can go for that price.

Skyscanner (for the Europeans)

Same idea as Kayak Explore (except better pricing if you are based out of Europe).

Because I’ve already gone through step 2, I know that we can afford a $150 round trip ticket somewhere.  Based on the fact that we are looking for a relaxing, beach vacation with Tapas style food and great hiking I can narrow it down to Portugal and Spain (I searched Pinterest for “beach” and “hiking” and the first thing that popped up was the best beach hikes in Portugal and Spain. ding ding ding!). After browsing through Pinterest and some of my favorite travel bloggers, I have narrowed it down to Lisbon and Faro in Portugal and the northern coast of Spain.


Now time for accommodation. I am not a huge fan of hotels. Actually, I really only stay in hotels on business trips or in areas I’m not really comfortable with (south east Asia for example). To truly live like a local I use these three websites to find some of the most unique places to stay:


iEscape is the perfect place to start looking at some unique, hip places to stay in your location of interest. They also have great travel guides and reviews of each location that will help you get a feel for each location. Once I have a general idea of the locations of interest and potential places to stay I pop over to Agoda to check out the best deals. But, before that I explore some more via Air Bnb.

Air BnB

Air BnB and Pinterest are my two favorite websites. One of my guiltiest pleasures is lying in bed till noon on a Sunday making various wish lists of places to stay around the world. If you click here you’ll get $30 travel credit for your first booking!


Agoda has some of the best deals around. It’s a little overwhelming though (kind of like TripAdvisor) so make sure you have a good idea where you want to stay before heading over here. If I found a place using iEscape, this is a good place to place your booking.

Now, I’ve saved some awesome places to stay and know I can afford flights to either Portugal or Spain. How do I go about deciding where we are actually going to go? By finding some extra cool things in each place of course!

Step 4: Micro-Research (What makes your trip special?) and make a decision!

Before I nail down the decision of where we are going, I first do some research on what there is to do in the two different areas. At this point, I have found a few places to stay in two different areas of Portugal with beach views and a few places in northern Spain along with a few places in southern Spain.

Pinterest searches

I start by putting in the place I want to go and I start creating boards for each destination. This could take as long or as short of time as you please. Like I said earlier, I could (and do) spend hours on Pinterest when I am planning for a trip.

After spending a few hours going through each destination, I was able to narrow down our choice to Portugal! The serene beaches, hiking, and relaxing nature of it all seemed to fit the bill perfectly. If you are still struggling to narrow down your option though here are a few more tips and tricks:

Twitter searches

Some of my favorite ways to find cool things to do in a city is to do some hashtag searches of those areas on twitter. With a quick search of #spanishbeaches on twitter, the very first result seemed like a perfect start if I were ready to explore Spain.

Surf some of my favorite bloggers to see if they have been to your destination

Hopefully, by now you have been able to narrow down where you are going. For us at this point, we have narrowed it down to the Sintra and Algarve region for one week in Portugal. Phew!

Step 5: Make a list of “must-dos”,  “want-to-dos”, and “No, thank you”

As you start to read through blogs, tripadvisor, and maybe even a Lonely Planet guide start making lists of “must-dos”, “want-to-dos”, and “No, thank you.” This includes activities, food, museums, castles, sunsets you can’t miss, etc. Make sure you don’t have more than 1-2 must-dos for each day that you will be in your destination. Otherwise, you might end up having too packed of a schedule to enjoy your vacation.

Step 6: Book your flights and accommodation

Note that I wait a while before I book my flights and accommodation. This is because I want to make sure I know how many days I really need. The last thing you want to happen is for you to book a trip and then realize you don’t have enough time to do the things you really want to OR you have too long in a place and you get bored (the hubby and I made this mistake in London). Take a look at your must-dos and try to situate your accommodation in a place that makes these activities more accessible.

For example, on this map you can tell where most of our trip will be situated so finding a place around Lagos and Portimao made the most sense. Try to find your accommodation and flight at the same time so you know how much each is going to cost before you book either. I almost always book both at the same time to make sure I am 100% aware of how much my two highest ticket items are going to cost.

Step 7: Lay out a rough itinerary of each day

I’m still a fan of GoogleDocs for this, but I just recently downloaded TripIt and I am starting to fall in love with it. I’ve also heard amazing things about Sygic Travel (formerly known as Tripomatic). Having a loose itinerary will help relieve a ton of stress once you are actually on vacation. We never have a strict itinerary, but always have a general idea of what we would like to do each day.

Step 8: Book a car if needed and any tours/excursions/cooking classes/etc.

This one is pretty self explanatory, but don’t wait until the last minute to book stuff! If you’ve done step 7 correctly, than step 8 will be done for you already. 🙂 Word to the wise – many of the coolest attractions are likely to be booked up. We made the mistake of not booking early for the Anne Frank House in Amsterdam and had to miss it as a result (no way was I standing in a 3 hour line).

Step 9: Make a packing list and pack your bags!

I’m really bad at this step.. This step sucks, but trust the person who has over 10 toothbrushes from various trips in her bathroom cupboard that not packing properly is never a good plan.

Step 10: Print everything out and go on vacation. You deserve it!

I always print all of our boarding passes, event tickets, hotel/airbnb reservations before heading out just in case our multiple devices can’t get internet once we arrive. Now, go and enjoy your vacation!

Do you have any travel hacks that make your vacation planning easier? Comment below with your favorite tips and tricks.

Happy Trekking!

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