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Diary of a made man

Hacking Travel – How to Travel the World for Free

by Ian Balina

A year ago


I know what you’re thinking.

Here’s another guy on the Internet making a shocking claim that has no possible application in real life.

I understand your skepticism completely. I was just like you a few years back: dreaming about traveling the world but thinking that’s impossible unless you have a trust fund. After all, “travel” and “free” aren’t the kind of words you usually use in the same sentence.

But, here’s the thing: it’s entirely possible to book a trip to an exotic location like Belize and pay practically nothing for it. Well, sure, you might spend a few dollars here and there to get a massage or buy a cocktail to that cute Balinese girl or boy, but other than that, most of the expenses (if not all) will be paid for in advance. I’ve had the pleasure of traveling to places like Tokyo, Rio de Janeiro, Machu Picchu, and the Dominican Republic, and most of the times either my flight or hotel were for free. Sometimes even both.

Don’t worry! You don’t have to be Rain Man to understand how to work with the existing rules set up by airlines, credit card companies, and hotels and use them to your advantage. Nor do you need access to an exclusive club that passes its secret knowledge from generation to generation.

Although it sounds sexy and dangerous, travel hacking is relatively straightforward.

So, how can you do it?

I’ll tell you everything about it in this guide. So, make yourself comfortable, grab a pen and paper and start taking notes because you’ll want to remember these hacks.

What Is Travel Hacking

First, a definition: Travel hacking is the process of collecting reward points and miles in exchange for free flights and accommodation. Banks usually purchase millions of miles and points from airline companies and hotels and offer them as signup bonuses for their new customers.

Bear in mind that the idea isn’t to spend tons of money to get miles but to “hack the system” and use credit card rewards programs to score points without overspending or having to travel a lot. Don’t worry: this activity is completely legal and even encouraged.

Anyone can get started with travel hacking. As I mentioned before, you don’t need to be a rocket scientist to understand how the system works and what you need to do to hack it. However, there are a few key points that you need to consider before getting started. For starters, you need to be well-organized (you will have to keep track of multiple credit cards, points, miles, and so on.) You also need to have a good credit score and zero credit card debt. It’s also paramount that you pay off your balance every single month and not pay any credit card interest. Travel hacking works best if you can avoid carrying a balance and paying interest. If you’re unable to do this, then it’s best to wait until you become fiscally responsible.

One quick note before we begin: I will be using the American market as an example, but that doesn’t mean that travel hacking is exclusive to the U.S. Other countries, such as Canada, the UK, Australia, Spain, and so on can work the system in their favor too. Use the tips and strategies in this guide and apply them to your local credit cards and programs.

Credit Card Rewards

I’ll be the first to admit it: reading about credit cards isn’t the most exciting way to spend an afternoon. But, learning how to leverage credit card rewards is one of the best and fastest ways to earn flights, accommodation, and other perks.

The first step is to apply for new credit cards that offer travel points as incentives to new customers. Be strategic about it and choose cards that can help you achieve a specific travel goal. For example, if you’re low on Visa points, then you should research the bonuses on Visa reward cards. If I want to visit Paris, I’ll apply for a Delta Airlines because they have a partnership wth Air France and I can use the reward points to book a trip to France.

In the past few months, I’ve applied for American Airlines AAdvantage card and received 50,000 air miles. That was enough to book a trip to Peru and climb Machu Picchu.

I’ve also signed up for Hilton Airlines HHonors, and Marriott Hotels Rewards credit card and received 80,000 points. I can use them to stay between three to five nights at one of their hotels, depending on the city and country I’m visiting.

These simple actions earned me 130,000 points that I can use to travel for free.

Choose Credit Cards Carefully

You can’t just apply for a new credit card, use the points, cancel it, and apply again. Most companies will require you to wait around 24 months before you can benefit from their sign-up reward again.

That’s why you need to be careful about the credit cards you choose and ensure that the sign-up bonus allows you to get one step closer to one of your travel goals. I usually don’t sign up for more than three new credit cards every year. With this strategy, I can meet any minimum spending limit (I’ll talk about it in a second,) and avoid any potential issues that might occur.

Issuers are less likely to approve you if they notice that you’ve applied for multiple credit cards lately. Chase, for example, won’t allow you to apply for a new credit card if you’ve opened more than five bank cards in the past 24 months.

Be Smart with Spending

In the movie “Up in the Air,” Ryan Bingham (played by George Clooney,) is obsessed with reaching the ten million frequent flyer miles. Rayan pays close attention to what he buys and how he pays for it so that he never misses the chance to earn points.

You should do the same.

If a credit card gets you two, three, or five points per dollar spent, then it would be silly not to take advantage of it as much as possible. For example, American Express EveryDay Preferred gets you three points per dollar spent on groceries. Or, American Express Premier Reward Gold earns you three miles per dollar spent on flights.

So, next time when you shop, whether it’s for airline tickets, hotel rooms or just grocery, pick the card that earns you the most points. After all, why would waste time to collect one point at a time when you can score three at once?

Use Airline Shopping Portals

Most airline companies and hotels have a list of preferred merchants that they partner with through shopping portals. By purchasing goods from these portals, you can earn more points than if you were to order them from regular stores.

Here’s an example. Let’s imagine that you want to purchase a new pair of jeans from Gap. Instead of going to their store and doing your shopping as you would normally do, use platforms like evreward.com or chashbackmonitor.com to discover the best deals across various programs.

You may find that by going to the American Express shopping portal and choosing Gap from the merchants listed there, you get three points per dollar spent. So, instead of getting 100 points for a $100 pair of jeans, you get 300 points for the same amount paid.

Leverage Your Job if Your Travel a Lot

I’m not bragging or anything, but airport lines are a thing of the past for me. And, so are the dreaded middle seats or waiting on hold when calling customer service. Instead, I enjoy complementary drinks and first name greetings whenever I travel.

I’m not famous or anything, but I travel a lot, and that allows me to score hundreds of thousands of points and miles per year.

Whenever I’m on a business trip or off to a conference in a different city across the country, I always take advantage of my airline and hotel loyalty programs. I have a company Amex credit card that I use to pay for business expenses. I then deduct all my travel costs from my taxes (I’ll talk more about this later.)  That way, I’m able to earn free reward points without actually paying for anything.

This strategy helped me achieve a loyalty status of Hilton Honors Diamond and American Airlines Platinum. As you can imagine, having an elite status comes with a lot of perks: front-of-the-line access, surprise treats, voyages to exotic destinations at the price of nothing, and complimentary upgrades, such as first-class or room upgrade.

Get Savvy with Manufactured Spending

Don’t assume that credit card issuers offer you miles and bonus points for nothing. Each card comes with a minimum spending requirement that you must achieve before you can enjoy the benefits. Most of them usually require you to spend between $3,000 and $5,000 in the span of three months. You also need to take into account the annual fees. Chase Sapphire Reserve credit card, for instance, comes with a $450 annual fee that they charge immediately or on your first month’s bill. You need to make sure that you have the funds to pay it. Otherwise, you risk acquiring interest charges on your first bill, and that’s the last thing you want.

Remember, the idea isn’t to spend extra money on scoring points but to hack the system and find ways to meet the spending requirements without incurring debt.

That’s where manufactured spending can come in handy.

Manufactured spending refers to the practice of purchasing cash equivalents, such as gift cards, money orders, and so on with rewards earning credit card. The goal is to earn miles or points for these purchases and then liquidate the funds and use them to pay the credit card. This strategy is usually used to meet minimum requirements or to achieve the flyer miles with a particular airline or hotel.

Here are some of the most efficient manufactured spending methods:

Pay Yourself with the Credit Card

By far the best way to meet the minimum spending limit is to pay yourself with your credit card and then pay the card back. Here’s how it works:

Use a platform like PayPal, Square or Venmo and email yourself an invoice to pay a bill. You can make the bill the entire amount of the minimum spending required or whatever you may need to hit the mark. Make sure to use a different email address instead of the one tied to your current account.

Use your credit card to pay for the bill. After paying it, the money will go to your bank account, minus a 3% credit card transaction fee. Use the money from the bank account to pay for your credit card at the end of the month.

By using this simple hack, you will pay just 3% of your minimum spending. In other words, a $5,000 minimum limit will only cost you $150. That’s a pretty great deal. For just $150 you can get a free roundtrip flight that would usually cost $1,000 or more.

Use Your Credit Card to Pay for Big Purchases

Don’t get the wrong idea. I’m not advising you to start spending money just so that you can meet the minimum limit. However, if it so happens to need a new computer or a new fridge around the time you’ve signed-up for a new credit card, use it to pay for this expense.

You can also use your credit card to pay for your friend’s and family’s purchases and ask them to pay you back. For example, if a friend of yours plans to buy a new sofa, ask them to let you put that purchase on your credit card. Then, instead of paying the store, they’ll send the money to your credit card. Or, if you go out to dinner with your friends, pay the bill with your credit card and ask them to reimburse you. That way, you can take care of the minimum spending for your card for the cost of a steak at a nice restaurant.

Take Advantage of Seasonal Bonuses

It would be nice if credit card issuers offered rewards on a predictable schedule. Unfortunately, that’s not the case, and you need to be diligent to ensure that you’re not missing on anything big.

Don’t let this thought intimidate you; there are numerous ways you can keep track of the best deals and take advantage of them. Loyaltylobby.com, for example, is an excellent platform where you can find updated lists of promotions for numerous hotels, such as Hilton HHonors, Marriott Rewards, Ritz-Carlton Rewards, and so on.

Using this method, I found out that Hilton has quarterly promotions that if you sign up for, you get 3x the number of points for each reservation. They also have a fantastic promotion that allows you to score extra points if you book a hotel room through their mobile app.

You should also pay attention to marketing offers that you receive via direct mail or email marketing. Sometimes, companies target deals to a particular audience group and don’t advertise them publicly. If you come across an offer that interests you, jump on it. Most of these offers don’t last long, so you’ll have to act fast if you want to benefit from it.

Keep Track of Everything Like a Pro

While working on this guide, I went to dinner with a friend of mine.

“How can you keep track of everything?” he asked me in awe as I was telling him about the different ways you can score extra points on rewards credit cards.

That’s how most people who get started with travel hacking feel. There are so many programs, and so many rewards account that it seems like too much of a hassle to get through all this trouble. Please believe me: it’s simpler than it looks.

For example, you can use Award Wallet to keep track of your rewards programs. Not only that, but this wallet will also notify you when your balance changes or when points or miles are about to expire. That way, you don’t risk losing precious points just because you were unable to track and monitor your loyalty programs efficiently.

Cancel Cards You Don’t Use Anymore

You don’t need a collection of airline credit cards gathering dust in your wallet. If you don’t use it or if it doesn’t benefit you anymore, then you should cancel it.

For example, I used my Alaska Airlines card for the sign-up bonus and canceled it once I didn’t need it anymore. The American Airlines personal card, on the other hand, comes with a lot of perks and I don’t mind paying the annual fees. So, I keep this one.

Business Expenses

How would you like to take a fabulous trip to an exotic destination and have Uncle Sam pay the bill when you return home? No, it’s not an illegal scheme that will get you in trouble, but a clever hack that allows you to travel around the world for practically nothing.

When it comes to traveling, entrepreneurs have the ability to mix business and pleasure. And, here’s the beauty of it: you don’t have to be the CEO of a fancy startup to benefit from tax deductions on your travel expenses. You can turn your blog or passion for photography into a business and write off expenses. For example, if you’ve set up a business for you travel blog, now you can go anywhere in the world and file all expenses on your taxes as a business expense. After all, you’re going there for business reasons – to create new content for your blog.

If you’re new to the business world, complying with the tax code may feel like navigating a maze. But, it becomes less complicated once you know what you can write off and what not.

For starters, you must ensure that the primary reason for your trip is for business. Otherwise, it would be hard to justify a 7-day trip to the Bahamas when you only have one day of meetings. A clever trick would be to count up the number of business and personal day on your trip. Keep in mind that the majority of days should be for business activities. For example, you could fly to the Bahamas on Thursday, have a meeting on Friday, stay and enjoy the weekend, meet with other clients on Monday and Tuesday, and fly back home one Wednesday.

Another thing that you should keep in mind is that you can’t just fly to the Bahamas with a stack of business cards in your wallet and call it a business trip. According to the IRS, you need to have at least one business meeting scheduled before you leave. Otherwise, you won’t be able to write off your expenses.

Which Expenses Are Deductible?

Here are some of the business travel expenses you can write off your tax bill:

Transportation Costs

You can deduct 100% percent of your transportation costs, whether we’re talking about bus, car or air travel. Be careful, though: you need to choose the appropriate option to be able to deduct your taxes. While flying first class is admissible, you don’t get away with deducting a two-week cruise you took to arrive at a business meeting.

Also, keep in mind that according to the IRS, your home is your regular place of business. So, if you work between Monday and Friday in New Hampshire and fly to South Carolina to be with your family during the weekend, you can’t deduct your travel expenses.

Lodging

You can claim your accommodation entirely. Don’t forget to ask for an itemized bill when you check out from your hotel. Some costs, like movie rentals or goods from the mini bar, might not be eligible for tax deduction.

Meals

You can deduct 50% of the cost of meals related to your business travel needs, tips and tax included. If you’re meeting with a client over dinner, you will have to document what business related topics you’ve discussed to pass the audit.

Other Expenses

Other costs that you can write off include conference fees, equipment rental, dry cleaning and laundry, shipping luggage, business calls, renting a location for a presentation, and registration fees.

You can’t deduct the following expenses from your taxes:

  • Family travel costs: You can bring your family with you on a business trip, but don’t expect to be able to write off their expenses. Sure, you can deduct your hotel room because you would have stayed there whether they were with you or not, but you can’t write off their transportation costs and meals.
  • Expenses in your city: You can’t rent a hotel room in your town and expect Uncle Sam to pay for it.
  • Personal extensions to business trips: If your trip was primarily for business, but then you decided to extend your stay and bring your family along, you can only deduct your business-related days.
  • Your daily commute: Transportation to and from your office can’t be write off as a business expense.
  • Lavish meals: Paying $400 for a bottle of wine and ordering only fancy food will probably get the attention of the IRS.
  • Any unreasonable expense: if you can’t justify it, don’t put it on your tax deduction documents.

Learn How to Use Expensify

If your business requires you to travel a lot, it can be challenging to keep track of all your expenses. Not to mention, it can be a tiring and time-consuming process. Fortunately, in today’s highly connected world, there are numerous mobile apps you can use to log and keep track of all of your expenses.

Expensify is one of my favorite ones.

You can take care of virtually any business expense, mileage or billable time with this app. All you have to do is import your credit and debit cards, and any transactions on them will be logged and categorized automatically. You can also scan and input receipts, organize them, and create an expense report. Whether it’s traveling for business, donating to charity or incurring any business-related expense, just snap a picture of the receipt and add it to your tax deductible report.

Then, when it’s time to file your taxes, all you have to do is pull your expenses by categories, and you’re ready to send your report to the IRS. It’s just as simple as that!

Airbnb

Would you pay for two hotel rooms and use only one?

Of course, not!

That would be silly.

Well, that’s what you’re doing whenever you travel. You book a hotel room and pay for it, but also continue to pay your rent or mortgage although you’re not using that space.

What annoys me the most about this problem is that the solution is rather simple and accessible to anyone. Instead of keeping your home empty while you travel, you could rent it on Airbnb and have your guest pay for your vacation. If you are lucky enough, you could even make a profit out of it. Just imagine returning from your holiday and seeing that your balance has grown instead of declining.

Here’s what you need to know about how to rent your house on Airbnb.

As a side note, I’ve already written an extensive guide on how to make money with Airbnb. So, if you want to dive deep into the subject, I recommend that you read this article here.

Below, you can find a few tips that can help you get started.

Create Your Account

Creating an Airbnb account is simple, safe, and free. Go to Airbnb.com and click on the Signup button. You can sign up using your email address, Facebook or Google accounts, or Amex. I would recommend that you create a unique email address for handling everything Airbnb-related. That way, you don’t risk missing an important notification just because it got lost in the sea of emails you receive every day.

Once your account is up and running, you need to focus on creating a detailed profile. Guests are usually skeptical about hosts that don’t provide enough details on their profiles. You don’t have to tell your entire life story, but provide enough information so that a stranger could feel comfortable staying in your house.

Get your account verified and include a clear photo of yourself in the profile. That way, guests will get the assurance they need that you are not a scammer.

Create Your Listing

Listing your home on Airbnb is incredibly easy. In fact, it shouldn’t take you more than ten minutes to create a listing. However, I recommend that you spend enough time on designing a listing that will awe potential guests.

  1. Use a Captivating Headline: Sum up what you have to offer in one short and captivating line. Don’t be vague, though. People don’t want to read an entire description to figure out if your listing meets their needs. Be brief and informative. Example: “Bright, Spacious Loft, 2 Block from City Center.”
  2. Write an Enticing Description: Give enough about your apartment and amenities, and describe your space accurately. Being deceptive can lead to poor reviews, which can break your entire Airbnb gig. Explain what’s available to guests, such as the number of bedrooms, what type of beds there are, whether they will have access to a private bathroom, kitchen, and a parking space. Mention if there’s Wi-Fi, cable TV, air conditioning, and so on.
  3. Use Great Images: One of the easiest ways to make your listing stand out is to use high-quality photos of the apartment. Take pictures during the day so that you can use the natural light to emphasize the beauty of your apartment. Choose the images that accurately describe how big your apartment is, how it look, what the neighborhood is like, and so on. Don’t forget to include a picture of your street since it can help guest envision their visit.
  4. Set House Rules: The great thing about Airbnb is that it allows you to set whatever rules you want your guests to respect. Take the time to think about your needs and your guests’ expectations and come up with a set of rules that will benefit both of you. Mention if you allow pets or visitors or if the guests should perform any house chores. Specify if you have a no-smoking policy or if there are certain silence hours that they should respect.

 

Set a Price

It should go without saying that people pay close attention to the price when renting an apartment on Airbnb. Do a bit a research to establish a fair deal for both you and your guests. Research your competitors and see what they are offering for the price they’re asking. Take a look at the hotels in your area to see what’s included in the cost of a room. If the market is highly competitive, you could offer a lower price than your competitors just to break the ice and get your profile noticed by potential guests.

It’s important to be flexible with your rates and increase it or lower it according to the market demand.

For example, if you know there’s an important event coming up next month, increase your price since there will probably be a flow of tourists. If you’re not traveling during that period, find a place to stay – maybe you can sleep on a friend’s couch for a few days or stay with your girlfriend/boyfriend until the conference is over. Then, you can use the money you’ve earned from renting your apartment during this busy period to fund a vacation. Or, you can just use the money from booking your apartment to travel somewhere until your guests leave.

Address Drawbacks Tactfully

Trust me when I say, no home is without flaws. The secret lies in how you are dealing with these drawbacks. For example, if you live in a noisy neighborhood, try to explain the reason for all the commotion. Maybe your apartment is located just a few steps away from the bustling city center. Or perhaps, you’re a quick walk to the train station. Are there any clubs, coffee shops or an exciting nightlife in your area?

Mention if your apartment is small, but also make sure to let your guests know that it’s cozy and intimate. Present the trade-offs: the apartment is small but it located right in the heart of the city.

Say if the building is old, but don’t forget to present the perks too. Maybe you live in a historical building, or maybe it just has a charming and cozy appeal.

As I mentioned early, don’t try to deceive your guest. You can be honest about how your apartment looks without being overly negative. If your listing matches reality, then you don’t have to worry that your guests will be disappointed.

Now you are ready to host! However, if you want to get good reviews and more bookings, you need to do a bit of legwork.

Be Friendly and Responsive: Airbnb rewards guests that have a strong response rate, so it’s important to reply to messages and booking requests within 24 hours. Keep in mind that you must always have the last word. Otherwise, Airbnb will list that as a non-response to the last message from the guest. It’s a bit annoying, I know, but this small “glitch” in the system can affect your rate. Make sure always to have the last word, even if it’s just a simple “thank you,” “great,” or “see you.”

Keep It Clean: Prepare your house before the guests arrive. Clean every room thoroughly and make sure everything is squeaky clean and that the sheets and towels are freshly laundered. The easiest way to get a negative review is welcoming guests in a filthy home.

Add Some Personal Touches: Going the extra mile can help you get positive reviews and, ultimately, make it easier to rent your apartment in the future. Simple gestures like offering to pick up the guests from the airport (if you’re not too busy, of course) or welcoming them with a basket of local goods can make a lasting impression on your guests.

In all honesty, renting your home on Airbnb requires a bit of work. You need to make sure that everything is in order, communicate with guests, and so on. But, the trouble is well worth it if it means that you can use the extra income to fund your vacations.

I use this hack every time I travel outside of the country. I list my apartment on Airbnb and try to have it booked for most of the dates when I’m not home. That way, I’m basically traveling for free.

Conclusion

Most people have a few aces up their sleeve when it comes to getting the best bang for their buck. They book flights on off-peak days, compare deals or rent rooms on Airbnb instead of hotels. But, while these tricks can help you shave a few hundred dollars from your holiday budget, most people still end up spending more than they would like.

Fortunately, there are other better ways you can see the world without breaking the bank. In fact, if you do this correctly, you can travel as much as you want without paying for almost anything out of your pockets.

Use credit card rewards to go anywhere in the world for free (or spending as little money as possible.) Learn what type of business travel expense you can write off from your taxes and have Uncle Sam pay for your trips. And, last but not least, rent your home on Airbnb while you are traveling to pay for your vacations.

Travel hacking doesn’t have to be complicated, especially now that you have a blueprint. Go out, try these tips, and live your dream. I’ll be here, waiting for your amazing stories.

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