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Whether you’re packing your bags for a summer trip to Europe or packing the car for a summer road tip with the kids, you may be tempted to define your vacation by what you’re not packing: your computer, tablet or mobile phone. As more and more of us struggle with the invisible electronic leash that keeps us tied to our (virtual) desks, it can feel like the only way to get free is to cut ourselves off from technology altogether.  More than one friend has excitedly told me that they’re taking their holiday out of cell range — so that it can be a real holiday.

I’m not beyond spending the occasional day off the grid — in fact, our own summer vacation plan includes a couple of days at a retreat centre with no cell coverage or wifi. But I’ve also found that my favourite devices and apps can make every stage of a family vacation more enjoyable — before, during and afterward.

Here is how we use some of our favourite apps to enhance our vacations — and our ability to remember them!

Organizing Your Trip

  1. Evernote: I create an Evernote notebook for each and every vacation we take, and use Evernote’s web clipper to compile lists of accommodation options, recommended restaurants and suggested activities. I share this personal guidebook with my husband, and we each save it as an offline notebook in Evernote on both our phones and iPads, so we always have access to our trip notes and ideas — even when we don’t have cell service.
  2. Airbnb: Inspired by the recent experience of immersing myself in the sharing economy for the report I co-authored with Jeremiah Owyang, I finally put our own home on Airbnb. The rental fees are not only subsidizing the cost of our long-planned summer vacation (part of which we’ll be spending at an Airbnb rental in another city) — they’re also allowing us to take more weekend trips. We’ve made our house available for most weekends this summer, and whenever we get a booking, we use the money to take a weekend trip…or to improve our collection of camping gear.
  3. Google Maps: Whether we’re trying to decide on which town to visit or which house to rent, Rob fires up Google Maps and uses street view to check out the neighbourhood. It’s a great way to get a feel for whether a particular community or location is going to suit us.
  4. RoadTrippers: My new favourite travel site is the beta version of a new-and-improved RoadTrippers, which lets you plan an itinerary much more easily and powerfully than you can do in Google Maps. Unlike Google Maps, which just gives you the total travel time for your entire trip, RoadTrippers shows you the drive distance and time for each segment….and then makes it easy to delete, rearrange or add stops if you want to adjust your timing (crucial if you have kids who get rangy after a few hours in the car). Cooler still, it can suggest everything from restaurants and campsites to scenic drives and attractions — all of them calibrated to your specific interests and the number of miles you’re prepared to deviate from your route. You can add points of interest to multiple “bucket lists” (I’m building separate lists for kid-friendly attractions, campsites and swimming spots) and then view them on your map at any time. And of course, you can sync to your phone using the RoadTrippers app.
  5. Craigslist/Ridejoy: The last time we were planning a big road trip (Vancouver to San Francisco), our desire to drive less and relax more led me to the idea of a one-way trip: while we hated the idea of driving for 16 straight hours with the kids, we knew they’d love an overnight train trip that allowed them to roam between cars. And taking a faster way back would allow us the time for a more leisurely drive down. The only problem: one-way car rentals are expensive, as are services that move your car between cities (yes, they exist). Our solution: posting to Ridejoy, a ride sharing service that included a lot of people looking for a lift from San Francisco to Seattle. When we were contacted by a responsible-sounding woman who shared a common point of contact (the service identifies any mutual Facebook friends), we arranged for her to drive our car up to Seattle while we took the train with our kids. She got the ride she was looking for, and we got our car back to Seattle for the cost of the gas.
  6. TripAdvisor: When we’re evaluating potential hotels, TripAdvisor is usually part of the process — but not based on the star ratings alone. I try to look at a range of reviews and get a sense of how people describe the positives and negatives of each option; that lets me figure out whether a given hotel’s drawbacks are going to matter to us.
  7. OpenTable: Travel is stressful enough without the additional drama of being hungry! The hungrier I get, the crankier I become…and the less willing I am to eat at some place that might represent a “waste” of this on-the-road culinary opportunity. Making advance reservations with OpenTable ensures I never get to that OMG I MUST EAT BUT I CAN’T FIND A TABLE state. I try to make reservations on the later side, as a fallback position in case we don’t find something we want to do on the spur of the moment.
  8. TripIt: I’ve written quite a bit about using TripIt for business travel in the context of Work Smarter with LinkedIn, but it’s also a fabulous way to create and share your itinerary while on vacation. Just forward all your random travel confirmations to TripIt, and their magic itinerary parser will chew through your confirmations and provide you with a nicely-formatted itinerary that provides direct links to things like airline seat recommendations and airline check-in. If you connect it to OpenTable, your OpenTable reservations will show up automatically, too. Again, there is a nice iPhone app that lets you see your itinerary from your phone.
  9. Hotwire, Expedia and HotelTonight: I keep a bunch of different hotel search engine apps on my phone so that I can search for last-minute deals when we’re taking a spontaneous overnight trip. These are the three that have impressed me the most in terms of both functionality and pricing. We got a great hotel deal on our last weekend trip with an Expedia rate that was mobile-only.

    Enjoying your trip

    Once you’re on vacation, the name of the game is play. Here are some of the apps that keep us (or our kids) amused while we’re traveling:

  10. Plex: I lavish attention on our home media center setup as if it were our third child. And when we go on the road for vacation, that effort continues to pay off. Thanks to the MyPlex service, which connects to the Plex media server we have at home, we can watch any show or movie on our hard drive from anywhere we have Internet access — even the car. Which is why we also have the rule: no streaming video over 3G when we’re outside the country.
  11. Audible: Our kids love listening to audiobooks, and Audible makes it easy to build and manage a collection. When we’re traveling, we make a point of downloading audiobooks related to our destination. (Sadly, during our recent trip to Hawaii, Sarah Vowell’s Unfamiliar Fishes lost out to the Beacon Street Girls’ Ready! Set! Hawaii!
  12. Location-specific apps: When we hit the road, I hit the App Store and browse all the apps related to our destination. We’ve had our trips enhanced by apps like Exit Strategy (tells you which part of the NYC subway platform as possible if you want to be as close as possible to the exit at your destination station) and Paris Pastry (where to eat carbs in the city of light). Before you leave home, search the name of your destination(s) in the app store for your mobile device to find the apps that might make your holiday that much tastier.
  13. Carcassonne: The iPad version of this excellent board game is our family’s go-to activity when we’re waiting for food in a restaurant. It moves quickly even with multiple players, it’s interactive (i.e. you will actually converse with your fellow players) and it allows for reasonably even play among players of different ages and skill levels.
  14. Scrabble: Look, you’re either a Scrabble person or you’re not. But if you are a Scrabble person, let me just point out that the pace of a competitive Scrabble game is singularly well-adapted to a poolside vacation with kids. While you take your turn, your partner watches the kids. When you finish your turn, you watch the kids while your partner tries to avoid crushing defeat at the hands of your 7-letter, 87-point burst of genius.

    Remembering your trip
  15. Yelp: If you like using Yelp to get the low-down on the restaurants, shops and experiences you may want to enjoy on vacation, you know that all those handy and amusing reviews have to come from somewhere. If you’re already using Yelp to find and bookmark potential watering holes and activities, you’re just one step away from compiling a travel journal that not only helps you remember your vacation, but helps other people plan theirs. Whenever I hear from someone who’s contemplating a West Coast road trip, for example, I point them to the exhaustive Yelp list I compiled when we drove from Vancouver to San Francisco. It’s fun for me to revisit, and even more satisfying for me to share.
  16. Facebook: When we’re on the road, I like sharing photo highlights with friends — as well as the Yelp reviews I write every day or two while traveling. Setting up a more limited Facebook list, which includes only the people who might actually want to hear about our road trip, allows me to share our travel news with a handful of friends and family….without boring and annoying all my other friends and colleagues. I get the added benefit of a one-stop overview of our trip, since both photos and Yelp reviews get archived to my Facebook timeline as long as I leave Yelp connected to Facebook.
  17. Aperture: Creating a photo book from all your vacation photos is a great way to create a memento of an exceptional vacation. You can do that using iPhoto, Shutterfly or many other photo book services, but I like using Apple’s Aperture to build my photo books, because it gives me more control over layout and formatting. I include some text reflections on our trip, and leave (carefully measured!!) blank spaces to glue in the ticket stubs, brochures and postcards we collected along the way.

What apps do you use on vacation? Let me know on Twitter, or in the comment field below.

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