How we booked our FAVORITE vacation yet!

portugalvacay

“How do you choose where you want to go when there are 1,000,000 places you want to visit?” - @kelsieoestdiek

I recently asked for any travel related content that you guys wanted to see on my blog, and one of the most common questions was how we choose where to go. This was a really fun question for me to consider, especially because just last week Peter and I spent 2 hours researching cruises that we could take asap, well as soon as the pandemic ends, that is.

Of course Asia, South America, Europe and Africa are all occupying the top spots on my bucket-list, but with so many countries, cities and small towns in each, it can be overwhelming to choose where to go first.

For Peter and I, 2019 was spent meandering around southern US and checking out places near our new digs in SC. (Check out our favorite southern cities!) But I would say our last big trip was to Spain and Portugal in 2018, which when typing that out, seems like an eternity ago. I worked 4AM shifts at Caribou Coffee during my senior year of college, saving as much money as possible to pay for a big vacation post-graduation. We knew we wanted to do something special, but the biggest question was where. With 3 weeks off before diving into our careers, we had a good amount of time to go wherever we wanted.

Consider this a case study of how we plan trips, because without very many limits, the world was really our oyster.

How we ultimately ended up on our favorite vacation

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  1. Dream big

First things first, when choosing a destination we considered elements like season, price-tag, group size, purpose (relax vs. adventure), etc.

  • We wanted to keep the budget around $1,500 for the trip, if possible.

  • We did NOT want to stay in hostels unless necessary. We have done that before & it’s a great way to save $, but we really wanted to treat ourselves and opted for hotels.

  • It was likely going to be the 2 of us, pending a couple friends who ultimately couldn’t make it, which meant the expenses of travel would be divided by 2 instead of 4

  • We were open to either adventure or relaxation, depending on what we found

2. Consult the Googs

Google Flights, man. I’ve said it once, I’ll say it again. It’s arguably one of my best friends. Is that sad? Maybe, but our bond is strong.

The best part about Google Flights is the “Explore Destinations” feature that allows you to see the prices of flights to anywhere in the world for any dates. What was nice for us was that our dates were pretty much set in stone, with a day or two of flexibility. This helped us narrow down destinations based on the cost of getting there.

My biggest advice is to know the currency. How far will $1USD get you? Sure the flight to Asia may be $900, but if it will only cost $20/night at a great hotel and food is cheap, that may be better than a cheap flight to Europe with high price tags for activities.

This is the point when we started to narrow down our search. Our top destinations being: Iceland, Peru, Germany, Spain, Portugal, Croatia and Thailand.

check out: my 5 Tips for booking cheap trips

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3. Are you going to use a travel company?

I never in a million years would’ve even considered this until Peter mentioned his parents using the company before. Although their website may seem sketchy, Trip Masters is actually a great place to find travel bundles. Basically, you enter your dates/cities of interest, and they will comprise a whole package including flights, hotels, travel, etc. Take note of the prices using this company as compared to booking it all on your own and you may just save some moolah.

Spoiler alert: We actually ended up using this for our trip!

4. Write it down

This is where I went mayhem. I think we probably had roughly 5 documents outlining each of our top destinations. Research is really key in determining where to go. I’m sure you have a few places in mind that are your dream destinations, but when it comes down to it, there are some practical questions to ask yourself:

  • Will this be in budget?

  • Is this a good season to be there?

  • How many cities in each country do we want to see?

  • If we are going to new cities, how much will it cost/how do we do it?

  • What are the costs of activities - museums, tours, etc.

  • How much time are we willing to spend traveling?

  • What are the layovers like?

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take notes!

This is where you can keep all the nitty gritty info that you might otherwise overlook.

5. make a pro/con list

I can vividly remember us sitting in a Panera reviewing all of our notes about each country. Ultimately, we were able to narrow it down to Croatia or Spain/Portugal, both of which would be in budget and offer a 12-day experience.

We eliminated the other destinations because of 1. Travel times 2. Difficulty of getting around (aka renting a car) 3. Overall shortness of the trip

With these two places in mind, we set out to compare our opportunities.

SPAIN/PORTUGAL

  • I had already been to Barcelona, but Peter hadn’t

  • There is a lot to see, so it wouldn’t be a very “relaxing” trip

  • We had heard Portugal was incredible

  • We could see 3 cities & 2 countries, rather than just one

  • It’s fairly easy to travel to each city

CROATIA

  • Neither of us had been

  • We’ve heard incredible things

  • We could stay at a resort & relax

  • There wasn’t a TON to do in the city, so most of the time would be at the resort

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6. Ask people you trust

We ultimately consulted friends from study abroad who had been to each country for their thoughts, and it helped us decide where to go: Spain & Portugal! We decided to pull the trigger and commit to our trip, submitting our payment via Trip Masters with butterflies quickly filling our bellies.

To this day, our trip was one of my favorites, if not my favorite. I’m sure anywhere we would’ve chosen would be incredible, but looking back, it was the perfect place for us! Plus, we found one of our favorite places in the world… Portugal. I cannot say enough good things about Portugal, but I’ll save that for another blog.

Read: The best of portugal - part one / part two


I hope this was helpful for your planning or at least gave you some ideas of where to go! If you ever need help deciding on a destination, message me because I’d love to help!

Cheers!

xoxo - Katie