Where Should You Start? The 2 Websites/Apps I Use for Trip Planning

As the designated 'free travel agent' in all my friend groups (though I don't recall volunteering for this position), I always get asked how to buy the cheapest airline tickets to get to places, and where to book the most cost-effective accommodation. I've had friends text me around 2-3 a.m. just to ask about these things (!) and sleep-deprived as I already am -- instead of telling them that there is such a thing as Google -- the midnight superhero in me always answers.

So for the benefit of all my friends, family members, new readers, and my periodically-over-caffeinated self (too much matcha = no sleep), I've simplified it all for you. Here are the top 2 websites -- both have app versions for your phone -- that I always check first when planning a trip. Click the underlined names to check out the websites.

Skyscanner My all-time favourite. I go to this site/app just for fun as I always like to plan months, or a year ahead, to where I want to go next. It's an aggregator, meaning it'll scour the web for websites offering the best airfare, hotel, or car rental depending on your input.

Getting Started

First, head over to Skyscanner (link will open in a new tab). You’ll be greeted with a clean, no-nonsense search bar—type in your departure city, destination, and travel dates. If you’re flexible, you can search for the “cheapest month” or even the “everywhere” option to find the best deals on flights to, well, anywhere! That's what I like to do from time to time: choose "everywhere," so I can see options I've never considered!

Finding Flights

Once you’ve got your search results, you’ll see a list of flights from different airlines and travel agents. Skyscanner is great because, as mentioned, it compares prices from all over the web. Use the filters to narrow down your options—sort by price, duration, number of stops, or even airline. If you're a night owl or an early bird, you can also filter by departure time. For example, I tend to fly on Friday nights because that's when I can get off work without booking a day off. So what I do is set the filter to flights that start around 5 p.m. or so.

Flexible Dates

Here’s a pro tip: If your travel dates are flexible, use Skyscanner’s "Whole Month" view. This feature shows you the cheapest days to fly in an entire month. Perfect for scoring the lowest fares. (This was great when I wasn't a permanent teacher yet. Oh, the days when I was a mere substitute...)

Price Alerts

Not ready to book just yet? Set up a price alert. Skyscanner will notify you when prices for your selected route drop. It’s like having a personal assistant who watches the prices for you while you sip coffee. I also use price alerts to study the price trends.

Exploring Destinations

Not sure where to go? Use the “Explore everywhere” feature. It highlights the best deals from your location to destinations around the world. It’s perfect for sparking some travel inspiration or finding a spontaneous getaway.

Booking Your Flight

Once you find the perfect flight, Skyscanner redirects you to the airline or travel website to book directly. This means no hidden fees from Skyscanner, just the best deal available. :)

Extra Tips

Multi-City Search: Planning a multi-destination trip? Use the multi-city search feature to find and compare the best routes and prices for your complex itinerary.

Skyscanner App: Download the app through your phone's app store for on-the-go searching. It’s super handy for checking prices and booking while you’re out and about.

Booking.com If your bank account is giving you major side-eye for those 5-star hotels you're lusting over, then go to this website or app to see charming options for a fraction of the price.

Getting Started

Head over to Booking.com. You’ll see a big search bar asking “Where are you going?” So, type in where you’re heading, slap on your travel dates, and hit that search button. Boom! You're already halfway to vacation mode.

Browsing and Filtering

Now, you’re faced with a mountain of options. Don’t panic! Use those nifty filters on the left. Whether you're a budget backpacker or a luxury lover, you can narrow it down by price, property type, amenities, and even guest ratings. It’s like online dating but for beds.

Reading Reviews

Next, let’s talk reviews. These are your best friends here. They give you the scoop on what’s what. Look for detailed ones—like, “The bed was as comfy as a cloud” or “The Wi-Fi was so slow I aged 10 years waiting for a page to load.” Honest reviews save you from surprises, trust me. Don't just book places without reading them! (I usually like to read if there are nearby convenience stores or supermarkets.)

Checking the Map

Got a list of contenders? Awesome. Now, click on that map view. You don’t want to book a “central” hotel only to find out it’s central to nowhere. (Happened to me and my husband... in Miami. It looked like the place was right beside the airport. Turns out there's a long-a$$ highway you need to travel on for 25 minutes before getting to the hotel!) Make sure your stay is smack dab in the middle of where you want to be. Use Google Maps or any GPS app to see how long it actually takes to get there to, and from, the airport -- or your friend of a friend's house that you're visiting.

Booking Your Stay

Found the one? Great! Time to book it. Booking.com often lets you book with free cancellation, so if your plans change, you’re not stuck. Just double-check the cancellation policy before hitting that confirm button. No one likes nasty surprises. Though, I must say, I've booked multiple Greek villas in Mykonos before, knowing I can just cancel the ones I don't like anymore... and I did.

Extra Tips

Genius Loyalty Program: This is exactly why I choose Booking.com for hotels and apartments! I love their loyalty program. Even if you don't travel a lot like me, sign up for the Genius program. It’s free and gets you cool perks like discounts and room upgrades. Because who doesn’t love a freebie? I've had a room or 2 automatically upgraded before because of my higher tier level in the program.

Price Match: Found a better price elsewhere? Booking.com has a price match guarantee. I personally have never contacted them about this 'cause their prices have already been the best, but hey, always good to know that you got the most cost-effective pricing for your stay no matter what.

Mobile App: Get their app for booking on the go and secret mobile-only deals. (Yes, properties can go even cheaper on the app!) Your phone just became your new, favourite travel agent. ;)

Well, that's all I got for now. I hope this was super helpful. This post is especially dedicated to my travel newbies and budget hunters out there. Happy travels, and may your next trip be full of adventure and zero Wi-Fi issues!