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  • Writer's pictureCait

How To Plan a Trip Series-- I: Where Should I Go?

When people come to me for travel advice, one of the most common questions I get asked is, “How do you plan a trip?”

If it isn’t this exact question, it is some variation. How do you pick where to go? How do you find cheap flights? Do you go through a travel agency or do you plan everything yourself?

I LOVE planning travel. I love finding new places to explore, researching the perfect places to stay, and putting all the details together in an itinerary. It’s why I started the #StealMyVacation series, so other people could benefit from my hours and hours of research.

But for those of you who want to plan your own adventure, I thought it would be fun to create a new series called #HowToPlanATrip to give a glimpse into everything I do behind the scenes.

For our first installment of the series, let’s start at the very beginning…

Where should I go on my next trip?

If you are a first-time traveler, or if you are looking for new inspiration, this is always a good question!

Picking a destination is usually the first step of the travel planning process and I determine my next trip in a number of ways.

Do a basic search based on preferred activities and travel style

I am an adventurous traveler. If you have read any of my “steal my vacation” posts, you already know that I prefer to “go and do” rather than “go and see.” That means most of my trips are to out-doorsy destinations instead of cities.

Our "first honeymoon" in Costa Rica right before we went zip lining through the rainforest

When I have a blank slate and I’m picking a destination out of thin air, I head to my favorite trusty search engine and search for some generic ideas. I may search “best destinations for adventure travel,” “beautiful landscapes,” or “adventure tourism” and see what comes up.

This is actually how I first learned about Patagonia—a relatively unknown region at the bottom of South America with some of the most gorgeous landscapes I’ve ever seen.

Fitz Roy Mountain in Patagonia between Argentina and Chile
Fitz Roy in Patagonia, between Argentina and Chile

Depending on your travel style, try searching “destinations for first-time travelers” or “best art cities in the world” to get your own search started.

This may be enough to pique your interest in a destination and then delve a little deeper into researching (which is a topic I’ll cover in a future post).

Follow travel brands and influencers on Instagram and Pinterest

Yep, in case you weren’t aware, Instagram and Pinterest are perfect for inspiration and stoking wanderlust.

There are tons of travel Instagrammers to follow. Try following the Traveldrops or Wall Traveled hashtag. Some Instagrammers I follow are @OurFamilyPassport, @TravelsofAndrea, @TheBlondeAbroad, @SheIsNotLost, @DesertToSeaTravel, and @TheWaltonAdventure (to name just a FEW).

In fact, it was thanks to Instagram I booked a trip to Turkey this year. (Seriously, just try Googling “Cappadocia” and tell me you don’t want to go there.)

Pinterest is another great place to get ideas and inspiration. Plus, there is the added bonus that you can save those ideas to separate boards for later when you get to the research phase! Pinterest fueled our first visit to Africa (and led us to the company we used to book our safari).

Giraffe on safari in Chobe National Park, Botswana, Africa
We loved the giraffes on safari in Botswana!

The one caveat to this method is that Instagram has contributed to over-tourism at certain locations. So don’t be afraid to visit secondary cities. But it is still a great way to get ideas!

Search by events or holidays

This method can help you decide where to go or where NOT to go.

Usually, when I am researching a destination, I will look into any local holidays that may increase prices and crowds. As teachers in China, we didn’t have much choice, but I can tell you from experience that you should not travel within most of Asia during the first week of October—China’s “Golden Week” when literally every person in the country travels by plane and train for vacation. Flights for us were ridiculously expensive and train tickets sold out weeks in advance.

Hong Kong, China skyline
We managed a short trip to Hong Kong during Golden Week, but it wasn't cheap!

However, traveling to a destination because of a festival or holiday is also a great way to travel. It could be traveling to see a favorite band play abroad, to experience a seasonal event (like the Christmas markets in Europe), or partake in a cultural festival (Holi in India is next on my list).

We are currently planning our 10th anniversary trip over a year in advance so we can time it with The Great Migration in Tanzania.

Search by season

Considering the time of year you can travel may dictate where you should and shouldn’t go based on weather alone.

I find traveling during the summer to be difficult. Not only because it’s peak season for crowds, but unless you are traveling to the northern or southern extremities of the map, it’s going to be hot! You may not want to visit the #Sahara in the summer when it’s a hundred degrees or #Patagonia where it’s freezing cold (since their seasons are opposite).

Sahara desert in Morocco, Africa
The desert was actually quite pleasant because we went in March instead of the blazing hot summer.

Drinks in Patagonia during the summer
This is us having drinks with some friends we made in Patagonia. I want to point out that it is almost 11pm and it is their SUMMER season--do you SEE my big, puffy coat!?

Most tourism bureaus divide their calendar into “seasons” based on crowds and weather. Peak season is obviously the time when the weather is nicest and most kids are out of school.

But I rarely travel during peak summer season. Instead, I travel during what is called “shoulder season.”

Shoulder season is a great time to travel—with better prices, fewer crowds, and more temperate weather. I have found April and October to be excellent times to travel almost anywhere in the world.

Iceland in September--it wasn't whale watching season (though we did still see a few!), but it was the shoulder season which meant we still had pleasant weather and fewer people.

We sneaked in a trip to Iceland in late September, right after the peak summer crowds, but right before winter snows closed down the mountain passes. We went to Costa Rica on our first honeymoon during the “green season” (aka rainy season) and endured afternoon showers, but otherwise green, lush surroundings.

Decide by price

Let’s be honest, traveling can be expensive, and you may have to make your decision on where to go based on cost alone.

Kayak has a neat tool called Kayak Explore, which allows you to input your general travel dates and budget and then displays where you can fly. It’s a cool feature that may turn you on to destinations you hadn’t previously considered.

You might also look at parts of the world where your money will extend pretty far. Since we have been to both Hawaii and #Thailand, I can honestly say Thailand is the much better option if you are on a budget. They are both pretty far away and a pricey flight, but we could stay at much nicer places in Thailand, afford almost daily massages, and overall preferred it to Hawaii.

Longtail boat in Thailand
I mean, y'all, Thailand has crazy blue water, temples, elephants, and THAI FOOD for goodness' sake!

If you need to travel on a budget, I wouldn’t recommend visiting high end resorts in the Caribbean or most places in Western Europe. Places I have been where our dollar has stretched very far?—Cape Town, #Bali, #Thailand, and Costa Rica.

But if a luxury trip on a budget is what you are after, I wrote a whole post about how we saved thousands of dollars on our dream trip to Africa here.


Hopefully, at this point you might have a short list (or even a long list!) of destinations that interest you.

From this point, I might narrow it down by season, budget, and how much time I actually have to take off. Then comes the part I love most, RESEARCHING! I’ve found that before I can make a final decision on destination, I need to dig into a few of the places to see if I would really enjoy spending my hard-earned dollars and PTO. I also determine whether I should enlist the help of local experts or go for a DIY trip.

But that, my friends, is another post in itself!

Pin for later! Or follow my Pinterest boards to stay up to date on travel, sustainability, and all things Disney :)

Did you find this helpful? Let me know if there are travel topics related to trip planning that you think I should cover in future posts.

Thanks, y’all!

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