This entry is part 1 of 4 in the series Web-savvy road trips

I’m just back from a week-long family road trip to the Oregon Coast, Portland and Seattle. One of the great virtues of a family vacation is its ability to separate us from our screens: to wean the kids from their daily fix of PBS edutainment, to interrupt the staccato sounds of videogame walkthroughs enjoyed on the nearest iPad, to prevent Rob and me from immediately distilling each experience into a 140-character summary. Those are (almost) all delightful parts of our daily existence, but taking a break from them gives us a chance to step back and reevaluate the role our various screens play in the rhythm of our family life, and to think about whether we want to make changes.

If I sound surprisingly calm about severing my connection to the Hive Mind for 7 days, perhaps that’s because I was the one person in our family whose screen time didn’t decline all that much while we were on the road. For a variety of reasons, we decided to let this trip unfold relatively spontaneously: when we hit the road last Saturday morning, our only reservation was for a Sunday night campsite on the central Oregon coast. So it was up to me, in my role as trip planner and navigator, to figure out each day as it unfolded. That meant I was on my iPad for several hours each day, sorting out everything from where to have an emergency pee to where we would sleep that night.

It’s the kind of adventure that would have been literally unimaginable for me in the pre-iPad, pre-iPhone days. I’m not a roughing it kind of gal — and by “roughing it” I mean sleeping in a cruddy hotel room. So the idea of trusting myself to the fates, and sleeping wherever we happened to land, would not have cut it. It’s only thanks to the iPad, and the ability to check out potential destinations while in transit, that I’m able to create the illusion of being a devil-may-care free spirit who can take off on a moment’s notice.

If you’ve got a tablet or smartphone, you can become a free spirit too. Here’s how to use your smartphone or tablet to book your well-priced accommodations from the road:

  1. Create accounts on several hotel booking sites before you leave home. We have accounts on Hotwire, Expedia and that way, if we find a deal on any one of them, it’s a snap to quickly complete a booking. Believe me when I say you will be grateful you entered all your address and booking preferences beforehand, so you don’t have to do it on your tablet’s virtual keyboard.
  2. Search multiple sites. My routine consisted of a quick Expedia search (to see which hotels had rooms), a TripAdvisor scan (to see which hotels got the top ratings), and then and Hotwire searches to see what deals were available. If something appealing popped up on Hotwire (which gives you better rates, but holds back the hotel name), I did a follow-up search on Expedia to see if I could deduce which hotel Hotwire was offering; by cross-referencing the location, amenities, star and TripAdvisor rating of a Hotwire offering, I could usually narrow the likely candidate down to just one or two hotels. Then I reviewed the TripAdvisor ratings on that hotel to see if I’d be happy to land there.
  3. Choose a daily booking window, and stick to it. Our first couple of days on the road, I felt like I spent the whole day on screen, scanning for potential rooms, but holding off on booking until we saw how far we’d been able to drive. Once we hit the gorgeous coastline I didn’t want to spend the day staring at my iPad, so from then on I tried to either take care of booking a room at the very beginning of the day (at which point we committed ourselves to being at a certain place by the end of the day) or to hold off until we arrived at a town charming enough that we felt like staying. If you take the “wait until the end of the day” approach, it’s still a good idea to start the day by looking at availability in a few destinations so you don’t find yourself driving past 2 or 3 towns with vacancies, only to arrive someplace that is all booked up.
  4. Search multiple towns at once. Our hotel booking process got a lot easier once I realized that I didn’t have to search for hotels one town at a time: instead, I could input “Central Oregon Coast” or “Northern Oregon Coast” as our destination, and and Expedia showed me all the options in all the towns in the area.
  5. Filter your search results. The hotel search process is a lot faster if you can narrow your search not only by location (town or neighborhood) but by rating, price range or required amenities (like a pool or room service). Expedia offers the most filtering options so even if you’re booking on, this is another good reason to start with an Expedia search. Why spend an hour browsing through 40 possible options if there are only 3 you’d really consider?
  6. Know your minimum viable deal, and jump on it. In general we were happy to get a 2.5-star motel for under $100, and a 3-star hotel for under $150. A couple of times I held off on booking same-day deals when they first appeared because I was hoping for something better (higher rated, cheaper, or both) and ended up having to accept a less-desirable option because the deal I was eyeing got booked up.
  7. Book 2 days at a time. Another way to avoid staring at the screen all day is to handle a couple of day’s worth of bookings at a time. If you’re driving a stretch of road that is remarkably unscenic, or held hostage in a shitty motel room while your kids catch up on sleep, you might as well use the time to book your next two nights; while the best deals are same-day you can also get lots of good deals the day before, and you’ll have more options.
  8. Book campsites a few days ahead. Ironically, camping is one of trickiest options for a pseudo-free spirit, since you typically have to book at least 72 hours in advance if you want to make an online campsite reservation with Reserve America. If you like certainty, book a few days ahead. Otherwise, you can try visiting a campsite and seeing if they have space: we got a space at the campground we wanted, and they still had vacancy by the end of the day.
  9. Travel against the tide. Since we were travelling in peak summer vacation season, we structured our traveling so that we were in coastal vacation towns during (slightly less busy) weeknights, and in cities on the weekends. That gave us more options and lower rates.
  10. Pick up the phone. Don’t forget that many small or independent hotels don’t participate in the big online booking sites. If you see a hotel reviewed on TripAdvisor but can’t find a deal for it online, call the hotel directly — we found a couple of places that way.

Of course, this system only works if you have a good data plan, so in my next post I’ll share my tips for roaming with your phone and tablet. I’ll have additional tips to share on tech-savvy road tripping in the days ahead, so do jump in with your own suggestions!

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