Travel Travel Tips

7 Proven Secrets to Book Cheap Travel

Every single work-day over the past 5 years I have woken up at the butt-crack of dawn with the roosters crowing, showered, brushed my teeth (90% of the time), and took my sorry ass to work. Why? That is the million-dollar question. The only answer is to fund experiences: travel, concerts, bar-hopping with a crew of my 10 idiot best friends. That is literally what every dollar I am able to save goes towards, and if I was able to save more to have more experiences I would! These secrets to book cheap travel are how we do it.

In the past 5 years, I have been extremely lucky to be able to fund European vacations, a tour of Southeast Asia, jaunts to US National Parks, and more. Now, Julie and I are not rich, we live in a 600 sq ft apartment for goodness sake. We’re going to share with you our 7 secrets we use while traveling to MAXIMIZE the number of trips we get to take and the length of those trips.

1.  Don’t marry the destination before booking

This is the most important in my opinion: seriously, it is CRITICAL. I’ve fallen into the trap before. You see some pictures or an epic video of someone in Sorrento or Belize, and you jump on to your favorite flight tracker and see that a round-trip is going to cost you $1000 and naming rights of your first-born. You have an emotional connection now, so you save your pennies away every day until you have enough to get the trip and you end up doing it! Took you 6 months, but you’re on your way!

I have a better way of doing it. Take 2 hours and research 10 places you would LOVE to go. That’s right, 10, at least. Your job is to find as many places as possible that you would love to go, before even putting those places into a flight tracker.

Would you be okay with anywhere on the Mediterranean, not just Sorrento? Perfect! There are 100 b-e-a-utiful cities on the Mediterranean, and I would venture to say you’ll be just as happy in any of them as you would in Sorrento (I really don’t have anything against Sorrento, it does look amazing…).

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Our Round Trip Flight from Chicago to Spain – Only $400!

Why are you still reading this? Go do your research, and once you have your list of cities then get your butt back here and read the rest!

2. Use flight notifications

Okay, you’ve got a full sheet of paper with destinations you’d love to go. Now you need to go to your favorite flight tracker and search round-trip flights from your home city. Compare the flight prices for each city right on down the line. Now I’m going to need you to use some judgment. Is this an inter-continental flight for less than $500? Well damn, you may need to book that right now my friend!

If you don’t come across a steal on your first search, that is okay, it is pretty rare. Enter your flights into a tracker (we love to use Google but feel free to pick your own!). Put in some ideal prices and sit back and let the software do the work, while you cut up a lime and plop that sucker in a corona and read the rest of this article.

3. When it comes to lodging: Location > Quality

I can’t stress this enough. If you are in a country or city you have never been to, you are going to want to be somewhere awesome. Ideally, pick a few locations within walking distance of places you want to go and things you want to see.

Now, I have some advice that may be unpopular. You don’t need your hotel to provide breakfast in bed hand-delivered and fed to you. You don’t need your Airbnb to have a California King with white drapes that pull apart to reveal a breath-taking view framed by palm trees on the balcony.

Yes, of course that would be nice, but remember we are maximizing fun while MINIMIZING costs. Cheap travel for the win! You are only going to be back at the place to sleep anyways. Who cares if you’re a tad cramped and have to share a bathroom after Taco Tuesday, get over it!

Our favorite ways to book are Airbnb, Hotels.com, and Hotel Tonight. Hotel Tonight rocks in terms of great deals, but you have to be okay waiting till the last minute! Find somewhere in an awesome location, sacrifice on amenities, and find a place to leave your luggage for your trip.

4. Negotiate!

If there is anything Americans (and even most non-Americans) skip while they are on vacation it is negotiating, and I have no idea why! Actually maybe I do, negotiating can be stressful and difficult to initiate. But sack up buttercup, do you want to save money while traveling or what!

The best place to negotiate (in terms of money saved) is going to be your lodging. Once you find a few hotels or Airbnbs you are okay with, give them a call. Tell them you have a budget of $X (depending on where you are) per night and you would love to stay if they can meet your budget. Make sure to highlight what YOU bring to the table.

You can offer them positive reviews on travel sites, check-in and check-out whenever works for them, or decline maid service for your stay. All these options help them, so they might be willing to cut you a deal!

When you’re out and about in the city, don’t be afraid to try some negotiating when you are buying food or a souvenir. In most countries it is socially acceptable to negotiate freely. Try and get two-for-one on an excursion or a free appetizer, I bet you’ll be surprised by how well you do!

5. Find free activities (hint: they are everywhere!)

Woof, we are 4 secrets in and I’ve already saved you 1000s! Why the heck am I doing this for free?

In every single city I’ve ever been to, some of the most fun activities I’ve done are free. F-R-E-E. More free than Lynyrd Skynyrd’s bird, folks! Keep those pennies in your pocket and come along with me.

My favorite free activity is the city walking tours. Sandemans has some awesome ones in big cities, but I would bet my bottom dollar that you can find a free walking tour in any city your traveling to. It is pretty generally accepted that people leave tips for the guides, but for 3 hours of entertainment and a newfound appreciation and knowledge of the city, it is worth it!

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Zion National Park

In most cities, there are excursions you can pay for that are not worth it. Climbing the Eiffel Tower, Chicago’s Willis Tower, Tower of London. All are entertaining, but you’ll spend more time in line than up at the top, and in my opinion I’d rather re-invest that time and money in something with more bang-for-the-buck.

Get a bottle of wine and watch the Eiffel Tower light up, take a stroll on the Chicago Riverwalk, hang out on the Thames under the Tower Bridge. All are better than the aforementioned excursions, and all have an entrance fee of exactly $0!

6. Leave the luggage at home, pack a backpack

This might be hard for some of you, but if I can convince my wife (who is beautiful and I love, but good lord 16 hair products and 34 skin creams? GTFO) to head to Asia for 3 weeks with a backpack then you can do it. I believe in you. Believe in yourself, and thumbs up for rock and roll!

Airlines will CRUSH you on luggage fees. Like an elephant would crush a cute little puppy (and your travel budget is the puppy my friend). But of course, we love puppies, and we love sticking to a budget, so leave your sixth pair of shoes (and your fifth and your fourth and your third) at home, zip up that backpack sweetheart. I swear you will marvel at how easy it is to fit a few weeks worth of stuff into 1 bag when you are thoughtful about it.

Added benefit, you are the fastest person at the airport! And it is so much easier to navigate a new city and find your lodging (in that awesome location…) without lugging a 49.95 pound container of bricks and hair straighteners and God knows what else.

One more thing, if you bring a full bag, then your wife is MUCH less likely to buy a stupid pink Coach purse that she’s used once since buying it (side note anyone wanting a pink Coach purse let me know…).

7. Picnic in the park > dining out

Picnics in the park are my JAM! PEANUT BUTTER AND JAM BABY! So so so so so much better than spending $100 for a hoity toity meal where they have to roll you out because you’re all hopped up and nitrates and butter residue. I will take a picnic 100 times out of 100, and that’s before considering that you can get an epic spread for $3! Grab a baguette, some cheese and sliced meats, maybe some peanut butter and jam, a couple apples, maybe a bottle of wine or a few brewskies, and have the best damn picnic that city’s ever seen! Keep your money in your pocket, you are going to need it for your next trip!

I gotta say, I feel robbed. I’m fresh out of ideas and you folks are going to be out planning your next trip for HALF AS MUCH AS IT WOULD HAVE BEEN WITHOUT ME. The least you can do is share some of your own cheap travel secrets with me.

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7 thoughts on “7 Proven Secrets to Book Cheap Travel”

  1. This is awesome. Thank you for the tips guys! I have the same problem with Annie and her 90 skin care products and hair accessories lol

    1. Lol ladies I tell ya! Biggest tip for that…contact cases. They are gold when it comes to packing your liquid goodies. Huge space and weight saver!

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