How I Travel to Five Countries Every Year and STILL Put Money in The Bank

As of this writing, I've now been to 48 countries. But don't worry, each country was not just another notch on my belt; I'm beltless. Each country was meaningful to me and beautiful, and for one split second, I thought I was going to be with them for the rest of my life. Now I want to help everyone get as many notches on their belt as possible. I've always wanted people to feel good -- like Halle Berry in Monster's Ball. I get more enjoyment introducing something new to someone and seeing their reaction than I do experiencing it for myself.

To all those people who ask how I can afford to travel so much -- out of applicable curiosity and not out of resentful assumptions -- make no mistake, I travel the world, have no debt, and still put money away in the bank.

Here's how I can help Billy-Bob-Thornton you and make you feel good...

1. DON'T BE DEAD SET ON SPECIFIC TRAVEL DATES

A lot of people travel with the idea of "maximizing" their vacation by leaving for a trip on a Friday after work, so that by taking five (or 10) work days off, they can sandwich two weekends around it, thus making it a nine (or 16) day vacation. (Full disclosure: I got an A+ in 2nd Grade Math -- then those sons of b*tches had to go and introduce multiplication and division! Can't wait for Trump to legitimize my "Multiplication Deniers" group!!! "Nobody can say for sure whether mathematics is real.")

While leaving on a Friday and returning on a Sunday grants you a few extra days, you'll also be paying top dollar. I save anywhere from $200 – $600 flying (when I actually PAY for a flight -- more on that later) and returning Monday through Thursday. Also, avoid traveling during the June through August summer months.

2. HOW TO FIND THE CHEAPEST TICKETS/ KEEP YOUR DESTINATION FLEXIBLE

If you already have the mindset that you're going to Paris and you're going to do it during a certain timeframe, you will be paying a premium to do so. When I travel, I know I need some portion of my trip to be on a warm beach. Because the earth is round and revolves around the sun -- I had to Google that -- there's always some country on earth that will be warm. (I had to Google that too.) This gives me plenty of options. To search for your flights, you should be using Google Flights (it's like I'm a paid sponsor for Google), which allows you to explore destinations on a map with loose or specific dates. You just have to put in your starting airport. It's great to see the prices of places by scrolling the map without having to manually type in each location.

Here's a picture for people who can't read good: Enter your starting airport with an empty destination...

Once I've targeted a few warm destinations that are reasonably priced, I go to Kayak.com to save time. There, I don't have to keep manually changing the start and end dates to see which travel dates will be cheaper for me. I can click "3 days before and after" from my chosen dates and I can also click on "include nearby" (airports), which allows me to save time on doing the same search with each nearby airport. Being in the Bay Area, I'm fortunate to also have San Jose (SJC) and Oakland (OAK), who both have international airports that can be cheaper to fly out of than San Francisco (SFO).

By golly, my math skills tell me that 9/12 to 9/21 is going to be the cheapest and longest trip!

Once I've targeted the best date and airport, I'll go to Skyscanner.com and type in the date and location and typically find the same ticket for $20 – $30 less than on Kayak.

3. PAY FOR YOUR FLIGHT WITH CREDIT CARD POINTS/MILES

Remember when I said "when I pay for flights"??? I pay for the majority of my international flights using rewards points from credit cards. Most credit cards will offer you some sort of bonus to open a card and spend a certain amount of money within the first three months -- typically $3k – $5k -- in exchange for 30,000 to 50,000 points/miles. That's the equivalent of $300 to $500 (most of the time more) worth of airline credit. And most of the time, they'll waive the annual credit card fee for the first year, which ranges from $50 to $99. Before that first year is over, consider closing the credit card or downgrading it to a card (in that company's lineup) that does not have an annual fee.

The only way that credit card can burn you is if you don't pay off your bill every single month and they hit you with the 20% interest. DO NOT EVER open a credit card if you can't afford to pay off the balance in full each month. If you can afford it, use that card for every single purchase. I charge everything, which means I've got about 2k to 3k extra points being accumulated each month to my card. Many cards also offer 2-for-1 and 3-for-1 points for purchases during travel, groceries, gas stations, and restaurants -- donkey shows not included.

A few cards that I have always liked are Capital One and Chase Sapphire Preferred. (Let me know if you want to open a Preferred card. I can refer you and get 10k bonus points. Unfortunately, you get nothing out of this, much like my sexual partners.) If you want to find out the best credit cards for reward points, check out The Points Guy travel blog. There's also this false notion that opening and closing credit cards will affect your credit. Check out this TEDx talk from a guy who hasn't paid for a flight in five years -- he can help debunk that myth. He goes in-depth into how these "credit card hacks" work. I know several people -- including myself -- who are doing exactly this to fund the majority of their travels.

4. SUBSIDIZE YOUR TRIP BY RENTING OUT YOUR ROOM OR YOUR HOME

My last two big trips were almost entirely paid for through the rental of my condo. I rented out my place in San Francisco for six nights and netted $1,300, which I parlayed into Ukraine, Lithuania, Latvia, Estonia, and Finland for two weeks and spent $800 on accommodations (it's cheap as heck out there!). I used the other $500 on miscellaneous expenses.

I use Airbnb to rent out my place, but, recently, they have fallen out of my good graces. After being a host for over four years and hosting hundreds of guests, I've been burned twice by them. Once as a host and the second as a guest. They will not watch out for you. I used to be one of the biggest advocates of Airbnb, but their customer service is horrendous. Anyhow, I'll save that story for another time. Hopefully, their recent $1 billion dollar fundraising round will be poured into a capable customer service team and management that actually knows how to put into place a process. For now, you can also list your home on VRBO, HomeAway, Tripping, and Craigslist for short-term rentals.

In San Francisco, my place can go for $230+ a night. In Cupertino, I can rent one bedroom for $100 a night. Sure, you have to get used to the thought of a stranger using your things, but that's why you get separate sheets, towels, require shoes to be off, and do a thorough cleaning upon return. Plus, I only accept people who are verified, have good reviews, seem nice, clean, and don't look like they'll be knocking da' boots all over my apartment!

5. DON'T OVERPAY FOR HOTELS

I see a lot of people splurge on lush hotel accommodations. I don't hate on anyone traveling their way, but I do worry that they are spending a disproportionate amount of money on these hotels when they should be out exploring the countryside, interacting with locals, eating street food, and being one with nature. If you're only taking one vacation a year, then maybe you should splurge. Since I know I am taking numerous trips throughout the year, I think long term. I'd rather have a two-week trip in a $150 a night hotel room, than I would a one week trip in a $300 a night hotel room.

A great site that I use, Hotels.com (avoid Hotel Tonight -- that app has burned me and does not offer better deals than Hotels.com), has a pretty comprehensive set of filters that allows me to find hotels above three stars, with cumulative customer review ratings, in the area that I want, and at the price I want. I always find a happy balance between luxury and value. I can still get a place on the beach with a pool, minus the 1000 thread-count sheets and doting hotel staff. I don't lose any sleep over it AND I travel longer.

You might also consider getting a private room in a hostel. Hostels are not what you once thought. This room had its own bathroom on the island of São Miguel, Portugal and cost me $50 a night. It's also a great way to meet people from all over the world.

6. WORK A JOB YOU LOVE

Perhaps the most difficult aspect for anyone to be able to travel frequently is to get the time off work. My main advice is to be damn good at what you do. Employers give you a lot more autonomy and leeway if they know you're not easily replaced. The best way to get to that point is to do something you love.

I may be very self-deprecating, but I don't believe there's anyone who is better at Public Relations than I am. Part of the reason I'm so good at PR is that I've traveled the world and talked to people from all walks of life. I thoroughly enjoy it. That allows me to fundamentally understand people and relate in a way that allows me to be better than others at what I do.

Have I been fired before? Yes. Many times. I'm opinionated and I'm passionate about what I do. I only regret the times that I didn't voice my concerns or I allowed myself to be bullied. I almost wish that everyone would get fired once in their lives. It's such a character-building experience. I've used those opportunities to travel and I've ALWAYS come back to a better work opportunity, with a clearer mind and focus. Opportunities open up for people who love what they do. And if you're that good, you can be your own boss -- there's nothing holding you back besides your own self-imposed limitations.

7. STOP BUYING UNNECESSARY THINGS! (This last tip is the longest, but most important)

Long before I even take a vacation, my entire life is geared towards saving money for that trip. Here are just a few of the things I do -- and each cost savings is the equivalent of one plane ticket over the course of a year:

• Cancel Cable. I cut my cable subscription eight years ago ($100/month = $1,200/year), which is more than enough money to pay for an international plane ticket each year — which, once again, I rarely have to purchase, because of my reward points. Another bonus of cutting cable? You stop watching idiots on reality shows and you start living -- and broadening -- your own life. If there was a news app that eliminated anything Kardashian, Kanye, Housewives, and The Bachelor, I'd be all over that.
• Order Water. Domestically, I almost never order a beverage with my meal (unless it's an alcoholic one at dinner and I'm going out afterwards), which saves me $2/$3 each meal. Calculate that at once a day, seven days a week? Total savings? $910 a year. It adds up! Added bonus? You lose weight!
• Brew Your Own Coffee. I rarely drink coffee, but I see many of my friends and coworkers do it EVERY, SINGLE day. Even if I did drink it, you can bet I'd brew coffee at home or at the office. Total savings at $4 a day? A whopping $1,460 a year. That's 28+ fancy dinners if you're traveling alone.
• Shop at Discount Retailers. Why people don't shop at Nordstrom Rack, TJ Maxx, Marshall's, or Outlets for the majority of their clothes baffles me. I'm not saying I don't have the occasional full-priced item -- heck, I even have a few $100+ tops (do guys call their clothes that?) -- but almost all of my clothes were bought at a discount, not including my already cheap, infamous white V-necks at a retail price of $24 for a 4-pack. I don't need to wear fancy clothes to feel better about myself or make people like me. They already naturally don't.
• Cut Your Own Hair. This is not something applicable for everyone, but it's just another example of an expense hack. I learned to cut my own hair as a teenager, when I wasn't happy with how they cut my hair at salons. This now saves me $20 every two weeks/$40 a month/or $480 a year. That could pay for your breakfast and lunch for 24 days on a trip. I'm also granted membership into bad haircut clubs, along with M.C. Hammer.
• Quit Smoking. I don't smoke, but I'd still like to serve this PSA. It's stupid. It makes you look like a dependent weakling. It's horrendous for your health. You stink. You make other people stink. You look like a moron standing out in the cold by yourself smoking and slowly dying. Besides that, $6 for a pack every couple of days? $20 a week? $80 a month? $960 a year on death? Idiotic. And, if you smoke a pack a day, we're talking about $2,190 a year! 

Please think long term! A few cuts now during inconsequential moments and you can maximize your traveling and make every day count. When I travel, I can go BIG and it doesn't worry me one bit, because I spend all year making small cuts. Because of that, I've seen Machu Picchu, scaled The Great Wall of China, dived The Great Barrier Reef, ran with the Bulls in Pamplona, cheered Team USA at the Olympics, samba danced in Rio at Carnaval, and... quite literally, I could go on. And on. And on. Really, you can do all this too.
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I've basically laid out a plan above where you can save upwards of $10,000 a year. That's a whole lot of trips! When people say they have to save money to go on a trip, I think to myself, I have never said that. Because it's ALREADY saved. No need to work the streets giving out handies anymore. That was just a high school job.

I truly want to help all of you travel more -- and for less. Travel is a gift that should always be shared. I can't tell you how travel makes you less materialistic, or how it alleviates your insecurities, or how you begin to love more and hate less. It's something you have to experience for yourself.

I am always here to offer you free advice. My reward is in you. (That sounded dirty....)

In this world, that has suddenly become more narrow and selfish, travel is what will keep us all humble and sane. Make yourself feel good and join me. We will experience this world together.


Sincerely,
Kevin L.
The Billy Bob of Travel