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Plan Your DIY Adventure: Choosing a Destination

Writer's picture: Katie MillerKatie Miller

Updated: Dec 22, 2023

Picking the perfect next adventure is an iterative process which requires creativity, research and flexibility.


My husband has had to put a rule in place, "no planning the next adventure until we finish one." I usually adhere to this rule, but have cheated on occasion and whether I can start researching while on a plane ride home as come into question as to whether it adheres to the rule. It makes sense though, enjoy what's in front of you! Since we just finished a trip, now I get to plan the next and people always wonder how I plan these trips so come along with me and learn some of the trade that I'm referring to as DIY Adventures!


I would love for international/cross cultural travel to be accessible to more people and the key to that is making it affordable. The first step in creating a budget international adventure is getting a great deal on the flight. The key to a great deal on a flight is flexibility in destination and time of the year. This does not mean you have to sacrifice and go during rainy season to a destination known for monsoons, you just can't go into the planning with the mindset of "I want to go to Italy in June". In that case, you've narrowed the destination and time of year and you will pay for it. You can still do it, it just won't be the best deal likely.


I have two tools which I use as my next-generation, digital 'spin the globe and put your finger on it' destination pickers. Kayak Explore and Google Explore. They each have their pros and cons so I use them both. Just take one look at either of these apps and I'm guessing you'll quickly start to see prices that you never imagined would be available, especially if it's reasonable to fly out of a major international airport hub near you. (We always drive the few hours to a major airport and opt not to travel from the small city airport near us.) Now that your hopes are really high, let me level set. Often times the prices that you see are weird days and long layovers. Not the most ideal flights. BUT they are a great starting point for honing in on a destination/timeframe/airline that is offering flights at a lower rate than typical.


Let's take a look at the two Explore apps capabilities! Let's start with Kayak because I'm pretty sure Google Explore was created subsequent to Kayak. It was brilliant! Just enter your available departure airport(s) and get a view of the entire world with price tags for the best priced flights in a designated timeframe to travel there. As you can see from the call outs below, Kayak offers the greatest flexibility in being able to set time ranges up to a year in advance and specifying a set range of days you are interested in or selecting a specific month. The month concept is cool to narrow it down, but I don't think it works well in identifying deals that start in one month and return in the next so I always play with the dates a bit after I found a good deal on a route to see if there are additional dates that would have the same price. The downside is that you can only enter one departure location and the UI has been glitchy the last few times I've used it. The biggest challenge though is when you find a great price on the map, but then on the next click that deal is non-existent. This has happened to me several times. (I'm sure it's not because they are trying to scam me, it's likely because they had to cache some information to improve the performance of the search and then the deal became invalid, but I'm not playing tech nerd on this blog and so it's not my problem and I want performance, multiple search criteria, the longest date range possible and accuracy in the map!)


Now for Google, the fast follower on this brilliant capability, they have made some improvements but also have some cons. Google allows you to enter in many departure locations which is great for people who live around a number of airports that we can choose to fly out of. I typically search all of NYC, Washington, and Philadelphia. The downside is it only searches for flights in the next 6 months, so if you are planning further out, you are out of luck. (I'm sure this is how Google is dealing with the performance and inaccuracy that Kayak is seeing above, but I still don't like it!) Additionally, you can't specify the number of days, you have choose from 'weekend', 'one week' or 'two weeks'.



So now that you have the entire world at your finger tips you can start to hone in where to go!


Ok that can probably be a bit overwhelming.


Some practical things to start to narrow it down a bit.

  • Although it's great to have a totally wide open schedule, sometimes we have an idea of when we want to plan it for.

    • Start zeroing in on a season so you can see the prices for that general time of year because there can be a huge variance.

    • Since we have to work around the school calendars now this has become a primary factor and of course always is more expensive. Before the kids were in school, traveling in Spring/Fall when other kids were in school was always the best deals, take advantage of this time before they enter kindergarten!

    • Most schools grant ~5 educational trip days. Use them and combine them with school breaks to be able to travel in the shoulder seasons.

  • How long do you think you can handle your kids on the plane? Notice, it's not really about how long the kids will last - toddlers fly on 15+ hour flights and survive every day, it's about what do YOU want to deal with.

    • Under the age of 3, I usually opted for flights that were less than or around 6 hours. There are so many places to explore!

    • By the time they are 5 or 6 and entertained by screens for extended periods of time, the world is your oyster but I'd ease into longer flights. Just like anything else, the more the kids are used to something, the easier it goes.

  • Below is a generalization of where you can go with direct flights from the NYC/DC area in various breakdowns of time. Obviously if you have connections, that would add to total travel time. My kids were always entertained just by being in airports and running around, so a layover can be a good break from the captivity of the aircraft.



So now comes the fun part. Click on some of these destinations and learn a little bit about them. Kayak and Google have both added functionality to help you become more familiar with the location as you search for flights to help you determine if it's a place you'd like to visit. I used to go to TripAdvisor to do some basic searching on a destination at this stage, and still do, but some of that information is built into Kayak and Google now.


The UI on Kayak again is a little wonky, but it has some basic information about the destination including some key sites and a bit about public transportation and getting around.



So let's say I like what I read about Medellin, Colombia. I usually click that 'Check Flight Prices' link just to validate that it's a real deal and that it's a flight that I might be ok with. Then, I start digging into Colombia! If I keep liking what I see, I keep researching what there is to do there! If I don't like what I see, I move on to the next good looking deal.


  • I do a basic Google image search to see if I generally like what I see in the country. I'm always a sucker for an amazing landscape and cute old towns.

  • I check out what the typical weather patterns are like for that time of year - I tend to avoid the height of rainy seasons.

  • I use Google maps to get a lay of the land around the arrival city. I see the city as the launching pad for the adventure around the country. I get a basic understanding of the provinces/states/departments of the country as that is what TripAdvisor uses to categorizes the areas with the country.

  • I use TripAdvisor to understand the attractions/activities. What are the highest rated activities in the country. What are some activities that our family would really enjoy? If I'm loving what I'm seeing, I may start a 'trip' on TripAdvisor and start saving things to it. This helps me see on a map where they are all located throughout the country.

  • Sometimes I look at tour agency itineraries to get an understanding of what is most popular to see. Rarely do I find an itinerary that I couldn't just straight up copy, but I like to customize what I do.

  • Is there anything culturally unique that is standing out? Tribal villages? Food culture? Farming villages? Jungle shamans? Religion that influences their dress and daily habits? I like to experience new things, so if it looks like something we have done before, I may pass.

  • WI start to identify 2-3 destinations within the country that have things we would really like to see or do. Then I have to figure out how do you get from place to place.

  • I Google for blogs on how to get around to those destinations. I just need to see that other people have done it and it's not terribly long, and get a basic understanding on the infrastructure options available (train, boat, one-way flights, car rental, hiring drivers, etc.) There will be another blog post on in-country transportation planning because navigating these options in other countries is just a little different than the US.

  • I also do research on the safety of the destination. Which I think I need an entire other post to discuss in its entirety!

  • I check to see if there are other airports that are actually closer to the activities we like within the country and consider if a multi-city flight may or may not make sense. I need to figure out if I want to book my main flight flying in and out of different international airports. I don't combine this purchase with an in-country airline ticket, so no need to have that planned out yet. Just the main ticket which you need first.

  • I scope out accommodations. I generally use TripAdvisor while I'm on it to identify some interesting, unique places to stay and get a sense for how expensive the country is.

  • So at this point, I have general idea on flight prices, average accommodation costs, costs of any major activity, and in-country transportation general costs - I get a sense for what the total cost of the trip will likely be.


I know that feels like a lot of steps and research. As I've done this multiple times, I can do it pretty quickly and know what to look for. In subsequent planning posts I'll go into more detail on these online resources that I use.


There is generally some wheeling and dealing needed to get the kids on board, at this point they have their own opinions on where they want to go. (Hawaii and Dubai generally top the list - not exactly budget locations!) Showing them pictures and videos of the various top attractions, landscapes, cities helps them to get a sense if it's something they would like. For the Asia trip, I had several different countries/cities in the running and let them help pick which ones they were most interested in.


Inevitably, I either buy the flight and then start doing deeper planning, or if the family really hates the idea or if the flight price jumps significantly before I pull the trigger, I may be back to the drawing board!


Upcoming Topics:

Plan Your DIY Adventure: Booking your Flight

Plan Your DIY Adventure: Picking your Accommodations

Plan Your DIY Adventure: In-country Transportation

Plan Your DIY Adventure: Building Your Itinerary

Plan Your DIY Adventure: Evaluating the Safety Factor


Feel free to make additional suggestions!

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