The Great “Dining Dash” Adventure of 2014

The other day I took on a mini-quest with my friend and fellow traveler Stephanie. We went to ten restaurants, cafes, and food carts in six hours as part of a challenge to earn dining miles. Here’s how it went down.

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Goal: Achieve VIP Status in One Day

Thanks to a company called Rewards Network, you can earn bonus points and miles at more than 10,000 participating restaurants throughout the U.S.

It’s a nice deal that requires no ongoing action from you once you register, which is free. You can register from anywhere in the world, you can use any credit or debit card when paying for your meal, and you’ll automatically earn miles when dining at participating restaurants. There’s no need to do anything at all besides registering your cards.

You register from the portal of your choice of airline or hotel partner. Here are links to a few of the most popular:

Register here for AA | Register here for United

Register here for Delta | Register here for Alaska

Once you’ve achieved a minimum number of “dines” each year, you move up in status, potentially earning even more points and miles. The maximum value arrives with “VIP” status after twelve dines, when you then earn 5 bonus points for every dollar spent on dining at participating restaurants until the end of the following year.

We wanted to undertake the challenge to make sure we reached our twelve dines for status in 2015… on a single day. We’d already had two each, so the challenge was to visit ten dining establishments in one day to complete the rest. It was an adventure and a mini-quest!

Rules of the Challenge

At the outset we agreed on some rules for what we called “Dining Dash” day.

1. On Dining Dash day, you can’t eat anything that doesn’t come from a restaurant or other dining establishment in the network. There are no exceptions: from the time you get up to the time you go to bed, all food and beverages must come from a “dine.”

2. That’s pretty much the only rule. But as a general principle, we tried to keep costs as low as possible.

Round I: Breakfast

We did our Dining Dash in Portland, and the first stop was the Village Inn, a place I’d never been to but felt very familiar due to my many experiences at Denny’s, IHOP, and (my favorite) Waffle House.

Over scrambled eggs and a small order of pancakes, we discussed our strategy for the rest of the day.

Total bill: $6.50 each (“Separate checks, please!”)

Fun fact: in addition to free Wi-Fi, the Village Inn offers a free slice of pie on Wednesday with the purchase of anything else. Why they haven’t been flooded with visits from every single resident in the surrounding zip codes is something I’ll never understand.

“How many points will I earn for these pancakes?”

After breakfast there was a lull in dining activity because the rewards program in our area has a shortage of diners and coffee shops. No big deal. We took a break to work for a bit and and go to a meeting, then planned to hit things hard starting at lunchtime.

Round II: Lunch

We regrouped for lunch two hours later and hit the streets. Our first stop was the Good Earth Cafe, which will be leaving the dining rewards program soon—but not yet. We both picked up an Odwalla juice for $2.95 each, then headed out to walk half a mile up to a pod of food carts.

Total bill: $5.90

Fun fact: Good Earth caters for nearby office parties, which brings up a great point: if you’re ever responsible for planning a party or business lunch, put the charges on your own card and get reimbursed. Once you’ve hit the higher status with Rewards Network, every $100 in spend earns 500 points.

Next, we wanted some food. Portland is known for its many food carts, but as far as we could tell only one of them is in the dining rewards program: Aybla Grill. Fortunately, it has five locations!

We went to the first one on SW 10th and Alder. I ordered a falafel sandwich for $5. Stephanie bought a soda and a side of warm pita bread—just $1.50!

After that we walked another few blocks to another location of Aybla’s at SW 5th and Oak. Unfortunately, our plans were nearly stymied when the food cart server declined to accept Stephanie’s Citi AAdvantage card for a $1 bottle of water.

Of course we didn’t have cash on hand—the whole point of the Dining Dash is to use a credit or debit card registered to the program.

The standoff ended when Stephanie offered to tip the server another dollar. Success!

Total bill: $6.50 at the first stop, $2 at the second

Fun fact: On the menu of side items, warm pita is just 50 cents, tzatziki is 75 cents, and a falafel ball is also 75 cents. You can create your own mezze platter entirely from side dishes!

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We were going to head to another side of town for the next visit, but on the way back to the car we used the Rewards Network mobile site to see if there were any other nearby restaurants.

As luck would have it, we discovered Dragonwell Bistro on SW 1st and Yamhill. The Chinese menu offered hot and sour soup for just $3. Boom!

Total bill: $6 (apparently, separate checks are not allowed at Dragonwell)

Fun fact: Dragonwell has its own frequent dining rewards program. Hardcore travel hackers in Portland may wish to enroll.

I used the time at Dragonwell to make notes on our adventures thus far.

Before we took another work break, we encountered another challenge: where to find a snack during intermission? Normally I have a pastry and coffee every afternoon around 3pm, but according to the rules of the challenge, I needed to pick something up before we each went home—and it could only be from a participating vendor in the network.

We got back on the mobile site and looked around. There weren’t many coffee shops in the network, but we noticed an Irish bar two blocks away. Might they have coffee? Maybe, but it was right after St. Patrick’s Day, so we decided to try our luck elsewhere.

That’s when Stephanie found something on the site that I had obviously missed before: pie!

The Pacific Pie Company is a participating establishment, offering nearly a dozen delicious pies available by the slice every day. I was very excited to check this place out and pick up a coconut crème mini-pie for the road.

Mmmmmmmm.

Total bill: $5.50

Fun fact: The pie place is run by an Aussie expat living in Portland. Thanks for bringing pie to our fair city!

I still needed a cup of coffee, and instead of getting it at the pie place, I wanted to see if I could earn another dine for it somewhere else. We first attempted to stop in at Lightbar, a bar that features cocktails and… sunlamps. I’m not sure about the concept, but we’d gone for drinks once before and the people were nice.

Unfortunately Lightbar didn’t open until 4pm, so we kept looking. A few blocks away we found Mad Greek Deli, a restaurant-plus-grocery-store-plus-bar I’d seen several times but never gone in.

I went in and was able to buy a takeaway coffee, so I was all set for the afternoon. Two more dines complete!

Mad Greek Deli: Your guess is as good as mine

Total bill: $1.95

Fun fact: We’re not really sure what’s going on at the Mad Greek Deli. If it’s ever in the news for something other than its inventory of tahini and pickles, we won’t be terribly surprised.

Gas Station Detour

On the way back to basecamp we also took a detour to fuel up the car—and we couldn’t go to just any gas station. No, we had to find a Shell station.

Instead of paying directly with a credit card, both of us go to Office Depot once a month and purchase gas cards for Shell. In another travel hack, when you use the Chase Ink Bold or Chase Ink Plus credit card, you earn 5x the points. You can earn up to 250,000 points per year, per card—and we do our best to max it out.

[Backstory: Read more about how this works.]

After fueling up, we paid the attendant with a Shell gift card and hit the road again.

Total price: $19.30 (95 Ultimate Rewards points!)

Fun fact: Oregon and New Jersey are the only states in which drivers aren’t allowed to pump their own gas. For some reason that has nothing to do with safety, you have to stay in your car and let an attendant do it.

Round III: Evening Drinks & Meal(s)

After another break, we regrouped and headed up to the Alberta arts district. Our first stop was Branch, a fun whiskey bar. I ordered a “49er,” a signature cocktail with ginger bourbon and honey. Stephanie had a hot toddy.

“Separate checks, please.”

Total bill: $16

Fun fact: This looks like a great “first date” place. I’m sure everyone there thought I was a terrible date, since I spent much of the time documenting the visit on my laptop and then asking the server for separate checks. But that was the whole point! We each wanted the dines to post to our individual accounts.

Next, we needed to eat. Ironically, despite going to seven dining establishments earlier in the day, I hadn’t eaten that much. The afternoon pie I’d lucked into was the most substantial food I’d had, so we looked for a real restaurant.

We ended up going over to NE Po 42, a few blocks from Branch.

I had a veggie burger and Stephanie had a side of pretzel bread with marinara sauce—a dinner of champions, I suppose.

Makin’ notes…

Total bill: $14

Fun fact: During basketball games for the Trailblazers, people who eat chicken wings can get them for 50 cents each (minimum order of ten).

For our final stop of the night, we headed back to my neighborhood and stopped off at the Triple Nickel, a dive bar that’s hilarious in the best of ways. I ordered a bourbon and ginger.

Ultimate bar games

Total bill: $4.50 (including 50 cent credit card surcharge)

Fun fact: Jumbo Jenga!

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Results & Cards We Used

We succeeded in making it to ten restaurants before the end of the day! We’re now set to earn 5x bonus miles in the dining rewards program from now through the end of 2015.

Here are the cards we used for our dines:

• Chase Sapphire (the best overall card for most of us, which provides double miles on all dining and travel spend)
• Chase Ink Plus (used for purchasing gift cards at office supply stores)
• American AAdvantage Citi Exec (Stephanie is trying to meet the minimum spend for her 100,000 point bonus)

A Few Tips & Tricks

Here are a few tips if you want to recreate your own Dining Dash, or even if you just want to register and then earn points on a regular basis.

Always tip your server. It’s the nice thing to do, and you also get points for it.

If you’re with someone who’s also doing the challenge, try to order things separately. Every charge counts as a “dine,” so there’s no reason to double up.

Not only can you pay with separate checks (two credit card charges) as we did, even if you’re on your own you can ask your server to split the bill between two cards. Note: to avoid being “that guy,” only do this when the total bill is substantial.

Plan for Happy Hour deals. Hitting up a bunch of dive bars in the late afternoon would be a great way to quickly get dines. Since we took a break between 3pm-6pm—exactly when Happy Hour takes place at most Portland restaurants—we didn’t plan well for this.

Another error we made: for best results, do your Dining Dash on the first Friday of the month, when Chase provides triple miles for all dining charges on the Sapphire Preferred card. (We did our challenge on a Tuesday and forgot all about First Friday until we were at the Village Inn for breakfast. Travel hacker fail!)

Win some, lose some. Next year, we’ll be more prepared.

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We had a great time with our first-ever dining challenge. I hope you enjoyed it, and I hope you’re earning miles too. Be sure and register with Rewards Network if you haven’t done so already!

Comments here.

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Tags: dining dash, frequent flyer miles, portland, restaurants, travel hacking