Behind the Scenes: How I Plan My Travel

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Every couple of days, I get an email or Facebook message or text from a college friend I haven't talked to in years asking me for travel advice. Advice on where to go, how to get around, what to pack. And, increasingly, advice on the best way to book travel.

And, I get it.

The Internet is great and has made travel SO much easier than it used to be. But it can also make travel (and travel planning, especially) a daunting task. When you go to Google and get literally MILLIONS of results from a search query, it can all start to feel rather overwhelming.

To help combat the information overload, I thought I'd take you behind the scenes today for a glimpse into how I plan some of MY travel.

The first thing to tell you about is a website called KAYAK.


(And, full disclosure, yes, I'm writing this post because KAYAK approached me, but I hand-to-heart, honest-to-God actually use them ALL. THE. TIME.)

KAYAK is one of the leading travel search engines out there, and I love it because a.) it's ridiculously easy to use and b.) they had these funny commercials a while back where people's fingers fell off (which made me dissolve into giggles every time).

These days, KAYAK is the first site I go to whenever I'm searching for a flight or hotel room – and they've recently added some really cool features to the site that make travel planning even easier.

Travel Problem Solved

KAYAK is in the business of solving problems for people, and recently launched a new section of its website that addresses a lot of the common questions/concerns that people have when planning a trip. Things like “Where can I fly on my limited budget?” or “I only want to go to warm weather destinations.” In the “Travel Problem Solved” section, KAYAK links to helpful parts of its website that take some of the stress out of planning a trip.

Travel Problem Solved from Kayak

Some of my favorites include:

“I don't know whether to book my flight now or wait.”

KAYAK offers a nifty price forecast feature on a lot of its searches. It will tell you whether you should buy now or wait a while, based on what it predicts the price for your flight search will do in the next 7 days.

Kayak price forecast

“I want the best price on a hotel.”

KAYAK doesn't actually SELL anything – it searches hundreds of sites for you, and then presents the best prices. When you go to book, you're taken to the site currently offering that price. So if you usually book your hotels through Agoda or, no worries – KAYAK searches those sites, too, and you can click over from KAYAK to make your booking.

“I want to know direct flights from my home airport.”

I totally get this sentiment (especially after an awful flying experience last weekend that included an 8-hour delay, getting shafted out of a free hotel room, and having my bag lost on the way home). If you just want to see where you can go with a direct flight, KAYAK has an entire page for that.

Kayak direct flights

“I want to go somewhere that's cheaper than it was last year.”

KAYAK also has a cool “Travel Hacking” section of its site, which offers lots of interesting info, such as what the hottest destinations are this year, what you'll find the best deals on, and more. It even shows you the most popular hotels in each popular/trending destination. (For example, some of the “trending” destinations right now include Milan, Rio, and Portland, Oregon.)

Kayak trending destinations

“Where can I fly on my limited budget?” or “I only want to go to warm weather destinations.”

One of my favorite features KAYAK offers is its “Explore” tab. It's a little bit hidden away, but once you find it you'll never look back! (Hint, get to it by clicking the tiles in the upper right corner of the site.) The Explore feature lets you set your home airport and the month/season you want to travel, and then you can search the entire world for flights based on price, region, and even average temperature! SUCH a cool feature – and a fun one, too, if you're not entirely sure where you want to go.

(This winter, it looks like I should look to Mexico or the Caribbean for warm weather and flights under $600!)

Kayak Explore

You can see some of these features (as well as some others that I like) in action in this walkthrough video that I made:

KAYAK also stands out to me on Twitter. I do social from time to time for another brand that has a real personality on Twitter, and I can say from experience that it's not always easy! So when I see it done *right* I can really appreciate it.

First of all, they do some great social customer service, even occasionally stepping in out of the blue to surprise someone with booking help or even a flight!

LOVE that. And they just have a sense of humor, too, which is often sorely missing from big brands on social:

If you're not currently following Kayak, check out their Twitter feed.

KAYAK definitely isn't the only site out there for travel planning – but it's one of the best, in my opinion, and if you haven't tried it before, give it a go!

What sites do YOU use to plan your trips?



Full disclosure: As mentioned earlier, this post was written by me but brought to you by KAYAK. As always, though, opinions are 100% my own. I love KAYAK!

"It's a dangerous business, going out your door. You step onto the road, and, if you don't keep your feet, there's no telling where you might get swept off to." - JRR Tolkien

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31 Comments on “Behind the Scenes: How I Plan My Travel

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  1. I’m pretty brand loyal to United and American so I can keep my miles in a few accounts, but I used to use KAYAK frequently to start my travel budgeting, getting a feel for how much I could expect to pay. I used skyscanner recently to find a great deal over Thanksgiving, but Hopper app is my go-to now for pricing out a trip.

      Yeah, I usually use Kayak for my initial searches – like you, to get an idea of what prices are doing. I haven’t heard of Hopper, but I’ll have to check it out!

    I tend to use skyscanner and because I live in Germany, I also use opodo that has come up troops especially with more complicated scheduling. I have nevertheless, heard of kayak but it’s not big in our region!
    Germans by nature are quite conservative. For example is NOW operating quirky commercials on German TV as the typical middle-class traveller had never heard of them LOL!

      It’s always interesting to see what sites are used/promoted in other parts of the world!

    Hey! Insightful post. Skyscanner is much more popular in Thailand. The last time I checked Kayak (admittedly some time ago 🙂 ) it didn’t have all of the features you outline above. Seems awesome, and I just checked and they have a Thai portal…I supposed I should have expected that from the Priceline Group.

    Thanks for sharing!

      I use Skyscanner sometimes, too! But I find Kayak tends to do better for flights originating in the US than Skyscanner. 🙂

    Earlier this summer I used Kayak’s Price Alert to get notifications of flight prices and I loved it! I always check out Trip Advisor to see what hotels are like before booking–pictures from the hotel staff are never quite the same as guest photos. 🙂

      The price alerts are great! I’ve used them in the past, too – sometimes I totally forget to keep checking flight prices otherwise!

    Oh Kajak sounds kinda fun, so I think I’ll give it a whirl 🙂

      Go for it! The Explore feature is especially fun to play around with.

    This is perfect, just what I needed! Haha I’m right now in Puerto Rico and just traveling around the Caribbean and then Central America, this will make my life sooooo much easier! 😀

      There are lots of really useful travel sites like this out there! They definitely make travel planning easier!

    I am hearing about Kayak for the first time and it sounds great! Will check it out, thanks for sharing Amanda!!

      Glad to have introduced you to it, Arti!

    These tools are so handy and really set Kayak apart from the other search engines available.

    But I’ve found that they often don’t find the cheapest price when it comes to flights outside of the US which can be a little frustrating sometimes. Thus I always use it in combination with another flight search engine as well.

      It never hurts to shop around! I also almost always book flights directly with the airline, which also sometimes means slightly higher prices.

    That’s awesome. I haven’t heard of those features before reading your post. I especially like the price forecast for flights. I always tend to waiting but lately the flight I was looking for was just getting more expensive and more expensive. Thanks for sharing that with us.

      The price forecast definitely is handy! You can set up price alerts, too, where Kayak will email you if the price drops.

    I just booked a trip to Edinburgh for New Year’s, and Kayak was like, Hey, you know you can save $150 by flying into Glasgow? LOVED that. Plus now we get to see Glasgow before taking a train to EDI!

      That’s awesome! I love that they really DO seem to want to help people find the best deals – it’s not just all hype!

      (Also, enjoy Hogmanay!! Edinburgh at New Year’s is SO fun.)

    I love Kayak too! One thing I recently discovered were the package deals (flight + hotel) and some of the options look awesome. I also love their ads from a few years back 🙂

      Oooh yes! Package deals can be a great option!

    I’ve never heard of Kayak before, but it sounds like a great website!! Thanks so much for breaking it down for me, it’s made finding my way around a LOT easier 🙂 Great info!

      Glad you found it helpful, Claire!

    I love using Kayak for trip planning! So many great tools on their site.

      It’s always cool to find a travel site that really GETS it, and does its best to make travel searching/planning as easy as possible for people.

    Ooo I really like Kayak’s price forecast option! I always wonder that when I’m buying tickets – do I buy now? Do I wait for them to drop in price? What if they go up in price? Leave that sort of thinking to Kayak it seems! I like!

      Yeah, it’s an awesome feature! It doesn’t work all the time, but it’s definitely handy when it does!

    Whilst i have heard a fair bit about Kayak, I have always stayed loyal to skyscanner, just because I found the prices were the cheapest and I love the everywhere and month by month or year feature. However, I do love the explore feature of Kayak mentioned in your post. I’ll have to check this out.

      I use Skyscanner sometimes, too – but Kayak is always the first site I check!

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