The completely new face of travel. High-speed travel hacking and toilet paper races.

How to hack a quick trip.


By Brad Beckstrom

Last month I visited Portland, OR. I was in town for 5 days attending a conference. The conference included lots of evening events spread throughout the city, as well as daily events downtown. I also had a dinner and a breakfast meet-up with friends on opposite sides of the city and a day long photo shoot, many locations. I did not rent a car, call a cab or set foot in a hotel.  I purchased cross country nonstop flights separately on Southwest at a total cost of $391. The return nonstop flight was particularly impressive arriving 20 minutes early and crossing the country in 4 hours and 40 minutes! Price for that leg was $186. What jet lag?
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I was elected captain of the toilet paper race team on one of the flights. These things just happen to me, I hear they don’t happen as often for other people.

While in town, I stayed at a very nice private home. The home was a short ride from the event and less than two blocks from hundreds of restaurants and bars on 21st and 23rd street in Portland. The owner left out an assortment of fruits, nuts coffee for me.  My total tab for four nights in these deluxe accommodations $323 about $80 a night.

I got around the city just fine using a combination of my feet, UBER and Portland’s cool light rail system called Max. If I were just to go back 30 years to 1985, many of my travel habits today would be completely unrecognizable. I’m not talking about flying cars or high-speed magnetic rail trains. Some might have predicted those back then if you asked them to describe the future of travel.IMG_1869

Actually, the planes, trains and automobiles are all pretty much the same. There are even more than a few commercial airliners over 30 years old that are still in the air.  What has really changed is how we interact with all this old technology.  Think about it, I’m staying in a private home getting around the city by streetcar, hitching rides. It could’ve been the 1930s.


What I’m experiencing is the completely new face of travel. Tapping into technology on sites like Airbnb, Kayak, UBER, Google Maps and Evernote. Even something as ubiquitous as Google maps is very impressive on an iPhone. I was able to see the schedule to the minute from my location to anywhere in the city using light rail system. I could see the fare and time distance to each stop. 30 years ago I would’ve been the last guy to jump on a streetcar and try to figure out a spaghetti map transportation system in a strange city.


By the time I returned home, I felt like I totally hacked this trip to Portland. Sometimes you have a lot of time to plan a trip, other times it’s coming up in a week. Regardless of my timeline, this is how I do it.

  1. I open up two separate browser windows on my laptop (not tabs) completely separate browser windows – one for flights, one for accommodations. If you don’t do this, you’ll end up with a lot of tabs open and get lost as you search for multiple elements of your trip.
  2. Flights are generally the most expensive part of the trip, so I start there. They often drive everything including dates, airports, sometimes even the location I’m going to. I start with a search on I also often select the flexible dates option just to see if there’s a big drop a day or two later/earlier.  Once I pick the dates, I set up a email or mobile alert from kayak.
  3. On, they have a nice feature that allows you to compare with another site. This depends on preference, I often use Southwest or Priceline. I recommend just picking one or you’ll lose yourself in a sea of browser tabs.  If you see the SouthWest Airlines banner pop-up that usually means they fly to that city from your local airport. It’s worth checking, this led me to the great deal I found on my Portland flights. This will open up a new tab in your flight browser.
  4. I set up an airfare alert with one or two services then leave it at that for a few weeks, unless I see an amazing deal or price drop. Have the alert sent to your phone as a notification or email so you can watch for price drops. The lowest prices are often between 40 and 60 days prior to departure. So if you’re only a couple weeks out, jump on any low fares. All you’ll have to compare them to was what the other airlines are charging. I group the flights by duration then scroll down till I see something reasonable.
  5. In the second browser window, I use kayak to do a hotel search in the same manner useually picking or Expedia as the comparison option. In a few seconds, I’ll know the going rate for hotels during the dates on in the city. I take a look at the map view to see where most of the nicer hotels are located, waterfront, downtown etc. this is a great way to scout prime locations. Then I open up a new tab and do a quick AirBnb search in that prime location and surrounding area.  With just these few sites, you have a very good idea of the lodging economy and any deals offered.
  6. In the case of Portland, the hotels downtown were expensive, many were over $275 per night so I focused my search on AirBnb and quickly found something in a better neighborhood for about $80 a night. Bam! Add that up over four nights and you just paid for the rest of your trip. Regardless, it always pays to search hotels as in some cities there are very good values. In Tampa, Florida, I found four star hotels for $150 a night. This can vary wildly. It all depends on the city and the time of year and rooms available to a discounter like  The nice thing is these will all show up in your kayak search. A non-prepaid reservation will cost you about $15-$30 a night more depending on the city. But once I purchased my flight I’m generally in for the prepaid.
  7. Once you find a flight or hotel, use Evernote web clipper to save your search or reservation. This will come in very handy when you arrive in the city or need to pull up any info on your phone. I would say of all of the travel tools I use Evernote is the most valuable. It works on any browser/computer/phone and syncs across all devices.
  8. Points. For most flights, frequent-flier seats are nearly impossible to get unless you’re going to Cleveland or Detroit in February. I use Chase Sapphire and Chase Bold for personal and business expenses. Chase offers options through to transfer points to and from cards as well as to airlines. This allows you to reduce the price of your flight using points if you make the reservation through If I find a great price on a flight on kayak, I will then put that information into Chase Ultimate Rewards and apply points to reduce the price of the already discounted flight. (If the exact match flight doesn’t come up, call them and they can pull it up)  Chase will even give a significant point bump 20% when the reservation is made through them. Worldpoints (many cards) has a similar program without the jazzy point bump or transfer options.
  9. Finally, I’ll do a quick search on Uber to make sure they or Lyft are available. On the rare occasion that I do need the dreaded Rent-A-Car, I’ll do a sorted price/ size search on kayak then compare it to any Avis/Budget discount I numbers I have. UBER is generally always less especially when you factor in parking.


Travel nerd stuff

Many people stop once they get the flight and accommodation squared away, but that’s where the travel nerds like me just get started.  The first thing I’ll do is create a map using Google My Maps. I’ll do a quick search for the hotel and save that on the map.  Then I’ll save any important locations, meetings, dinners, photo shoots etc. This gives you a great picture of the city that you can pull up on your phone later, and you’ll always be able to find your way back to your hotel. You can also do random searches like restaurants and zoom out on the map to see where some of the active parts of town are. Save anything that looks interesting on your map and it will give you a feel for the place.  Once you arrive, you can pull up Google maps on your phone and see you where you are in relation to your saved locations. All your reservations and plans will be saved in Evernote. I’m generally able to use all this technology when traveling just with an iPhone and sometimes an iPad.


Happy Trails

The Frug



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