Part of being a smart risk-taker is seeing and acting on opportunities. That’s why I’ve always been attracted to the points and miles game of travel hacking.
The big travel companies of the world have worked hard to build loyalty programs so you’ll spend more money to use them. But if you study their offers, you’ll find lots of ways to reap the benefits of these programs (read: free travel) for a very small investment of time and money.
Oh, and it’s also a lot of fun to game the system.
Here’s how it turned out, and the big travel benefit you can get from it.
The Portland Dining Dash Challenge
In the land of travel hacking, a company called Rewards Network (RN) maintains relationships with tens of thousands of small restaurants and chains across The U.S. When you eat at one of them, you automatically earn miles in your favorite airline program1.
If you eat at 12 of their restaurants in a year, you earn VIP status and start earning five miles for every dollar you spend. That’s when things get interesting, especially when you pay for your meals with a card like the Chase Sapphire that earns three points per dollar for dining out on the first Friday of the month.
If you like to go out to eat and you spend $250/month to do it, that’s a free plane ticket every year for no added effort.
But that requires you get to VIP status in the first place. And why spend a whole year and a lot of money doing it?
The goal of the Dining Dash was to reach VIP status in one day by visiting 12 restaurants while spending as little money as possible so we can rake in the miles for the rest of the year. I chose $502 as an arbitrary limit for myself.
Stop #1: Isabel’s
Order: Side of bacon
Running Total: $3
The first challenge we ran into was getting breakfast. There are many RN restaurants in Portland, but not many open for breakfast, and restaurants come and go from the program. Despite Steph’s careful planning, our favorite spot disappeared from the program the night before!
After a quick regrouping, we ended up at Isabel’s in NW Portland. My $3 side of bacon was delicious, but required a bit of convincing to the server that yes, that really was all I wanted. Check please!
Stop #2: Theo’s
Order: Savory waffle
Running Total: $7
Just up the street from Isabel’s is a new café called Theo’s, a recent addition to RN, where we stopped for second breakfast and my first mistake of the day—a giant waffle.
Stop #3: The Doug Fir
Order: Fruit bowl
Running Total: $13
The Doug Fir, a favorite concert venue of mine is also surprisingly useful for a dining dash. At this stop, we sat down with Sandy, the local RN rep, who interviewed us about our challenge. She gave us a few dining tips and we gave here a few travel ones. Fair trade!
After the waffle debacle at Theo’s, a fruit cup was all I could stomach for third breakfast (most important meal of the day!).
Stop #4: Pacific Pie Co.
Order: Tonic Water
Running Total: $16
There are few things better than a carefully crafted hand pie. The Australian delicacy is a savory, delicious treat worthy of all the culinary praise it receives. And I didn’t eat one because my stomach was in no shape for it. A fancy tonic water was a disappointing substitute, but an effective stand-in for the Pepto Bismol that wouldn’t have earned miles.
Pro-tip: Always base medical decisions on award point values.
Stop #5: Pita Pit
Order: Jalepeño potato chips
Running Total: $17
A NW favorite for opening early and closing late, we wanted to get one more qualifying dine in before a proper lunch. Pita Pit to the rescue! A $1 bag of jalepeño potato chips did just the trick.
As I approached the checkout, the attendant smiled and asked, “Did you just buy these so you could use the restroom?” My emphatic reply: “No, I bought them so I can fly to Asia for free!”
Aybla Grill Hoda’s Lebenese
Order: Lentil Soup
Running Total: $22
By lunch time, we found ourselves in a truly unexpected predicament: actually hungry.
An ill-timed lunch coupled with an airport pickup and a closed Lebanese food cart left us scrambling to pick up our 6th dine before the afternoon progressed too far. Thankfully, we were able to regroup and satisfy our craving by visiting Hoda’s on SE Belmont, one of the neighborhood’s other 650 million3 Lebanese restaurants.
Halfway to VIP!
Stop #7: White Owl
Order: Green Tea
Running Total: $24
By 3pm, we’d entered a kind of Portland Twilight Zone rich with opportunities for cheap qualifying dines. Others call it “happy hour.”
We make our first happy hour stop at a fun bar called The White Owl. Chris and I drink a decidedly un-fun cup of green tea while the bartender wonders to himself, “WTF?”
Stop #8: Star Bar
Order: Vegan Jell-o shot (seriously)
Running Total $26
One of my favorite things about RN is they maintain an excellent stable of grungy dive bars. Our next visit was to the Star Bar which easily earns that title. A $2 vegan4 Jell-o shot (cheapest thing on the menu) got us through our eighth dine, but only after a passive aggressive bar tender who kicked us out for showing up four minutes early softened his heart and invited us back in.
Stop #9: Slow Bar
Order: Wedge salad
Running Total: $31
I knew I couldn’t top the quality of the vegan Jell-o shot from the Star Bar so, for our next stop, I opted for food only—a $5 wedge salad.
It’s now 4:30PM, and my wife, Jess, joins us breathe some life back into our tired and restaurant-weary group.
Stop #10: La Calaca Comelona
Order: Two chicken tacos, club soda
Running Total: $39
Say that five times fast! We’re entering the final stage of our challenge and success seems all but assured. It’s time for dinner, so we find this understated Mexican joint with an extensive happy hour menu.
We’re now six dashing diners. This is the point at which explaining that everyone wants separate checks gets a little harder to manage.
Stop #11: Church
Order: Bulleit old fashioned
Running Total: $48
In classic Portland style, someone decided it would be fun to say, “I’m going to church for a drink,” so they opened a bar and called it that. And it is fun, so we stopped there next.
But now, I’m a little worried. Drinks at Church are expensive for Portland (God keeps it classy), and I only have $11 left. So, I devise a strategy. I spend $9 on my favorite—an old fashioned—and resolve to barter with the barkeep at our last stop for anything he’ll sell me for $2.
The old fashioned goes down with mild trepidation. One stop to go!
Stop #12: Triple Nickel (Grand Finale!)
Order: Tequila Jell-o shot (again, sigh)
Running Total: $50
Regulars to this haunt call it by its hipster name, The Trip Nick (only two syllables are allowed in a hipster name). I try it on for size, but feel like a fraud. I’m wearing a button down shirt, after all. Regardless, The Trip Nick comes through for me, delivering yet another Jell-o shot—the only thing on the menu under $2. Now I remember why they were so popular in college.
Here, a host of Riskology readers and travel hackers alike join in to celebrate the evening. The DJ blasts 90s dance music to an empty floor as Chris, Steph, and I finish off the night with our go-to celebration drink, a shot of the fine Fire Ball Whiskey. And, like a true chump, Steph pays for mine because I’m out of money.
Tips For Constructing Your Own Dining Dash Challenge
Are you intrigued? Hungry (for frequent flyer miles)? Disgusted by our day of gluttony? Want to create your own dining dash challenge and swim in a sea of miles and points? You can! And here are some of the best tips we gathered throughout our day of feasting to make your own challenge a little easier:
- The sides menu is your friend. There’s a lot to eat on a 12-restaurant tour. If possible, order small dishes from the sides menu at each stop.
- Check restaurant status before you go. Restaurants are regularly coming and going from the RN program, and some only offer points on certain days of the week. Be sure to check the RN app before you head out.
- Plan your meal choices. Your stomach probably isn’t accustomed to eating 12 different things in one day. It’s best to plan your meals out in a way to reduce… um… gastrointestinal distress.
- Look for low-service restaurants. Pay-at-the-counter joints are the easiest to manage when you’re in a group.
- Keep your group small. The more checks you need, the more annoyed your server becomes. We learned you can combat this, though, by explaining exactly what you’re doing and letting them in on the fun.
- Ask for separate checks from the beginning. As soon as you sit down, let your server know everyone will be paying for themselves. Repeat this throughout your dine to guarantee you actually do get separate checks.
- Go non-alcoholic during happy hour. Happy hour is a great time to pick up cheap qualifying dines, but you could wreck yourself before dinner if you’re not careful. Tea (or any other non-alcoholic drink) is an odd but wise choice.
Also, congrats to Chris Creed who won our #DiningDash Instagram challenge. Enjoy the 2,500 miles, Chris!
1. See the Dining Dash intro article for a rundown of available airline programs.
2. This number does not include tips because, technically, you don’t have to pay a tip. But, of course, I did. And, for small purchases, tips were often 1-200% of the total bill.
3. Rough estimate.
4. Yes, really.
You can read Chris’ dining dash report over here.