• by Steve Smith , Staff Writer @popeyesm, July 17, 2012

We were somewhere around Barstow on the edge of the desert when the drugs began to take hold. I remember saying something like, "I feel a bit lightheaded; maybe you should drive... ."

--Hunter S. Thompson

Somewhere outside of Siena I wished like hell the drugs would kick in. No such luck. This was no Hunter Thompson road trip. No hip and stoned lawyer traveling buddy. No trunk of psychedelics. No waves of flying bats.

Just my daughter barking about the wacky GPS on my iPhone, which she was using to navigate our family caravan back onto a recognizable trail in two vans traversing the Tuscan countryside. But it was a plan no less wigged out than Thompson’s infamous Vegas sojourn. Because who wouldn’t want to have three modern blended families in the Italian countryside trying to come to consensus over what to do next? My mother. her second husband, my sister, her blended family of daughter, son and second husband, my second wife and daughter were all packed into two underpowered diesel crossovers to find their way across cryptic terrain. And me driving lead, wishing the drugs -- any drugs -- would kick in. What could possibly be wrong with a plan like that?

“We’re semi-officially lost.”

“How can we be lost?” I answer.  "We were on the path back to San Donato just fine. I thought we had it this time?” At this point my niece and nephew were considering throwing themselves down one of the many treacherous ravines rather than spend another minute with this hapless crew.

“The blue dot just jumped to the other side of that valley. We’re not where I thought we were. This iPhone is too frustrating. I don’t want to navigate anymore.”

We were lost…For the fourth or fifth time, only three days into my mother’s misguided romantic vision of an ideal family vacation. If I get out of Tuscany alive, I swear I will burn every Diane Lane film and Rick Steves video in her collection. Next time we go to Disney World, where the streets were designed by an obsessive midwesterner, all roads lead to Cinderella’s Castle, and there is an app for this.

At this particular lost moment, when both SUVs were on the side of the road while my brother-in-law and I considered how to un-lose ourselves this time, my mother yells from the backseat, snidely: “You did see the sign we passed that said San Donato, didn’t you?”

“Ma, four people so far have given us different directions to San Donato and every sign we ever followed toward this place got us even more lost.” She, whose underdeveloped Tuscan fantasy was the root cause of this, had been sniffing at the gadgets all along. Apparently Tuscan Sun romanticism doesn’t involve cell phones -- only grapes, orange sunsets, rolling brown hills and swarthy groundskeepers ready for a summer fling. “Ma, if you want to call Rick Steves directly to get us out of this, be my guest. But all you got right now is me and an iPhone’s geolocation, so I would go with that.”

The gadgets on the whole saved our asses more than once, but they also offered a false sense of comfort. Daughter, wife and I were all armed with iPhones, international messaging packages, and a roaming data plan for my line just in case we needed it.

And did we. All things considered, the iPhone’s GPS plus Google maps themselves got lost among the Chianti hills as often as they worked. Like most American tourists, we were exporting our expectations and habits to a foreign land.

Where geolocation became absolutely invaluable was in Florence proper, however. Even our discordant band of unmedicated travelers swept past the tourists fumbling with their unwieldy accordion maps on street corners peering down alleyways. In most cases we popped in specific locations, whether it was our parking garage, Pitti Palace or the market at San Lorenzo and followed the blue path. It is hard for me to imagine how or why smartphone users would resort to paper mapping once they start using mobile street by street directions. In a few years, the streets of legendary cities no doubt will be filled with people following their smartphones to and fro. This is a problem that mobile media solves.

Needless to say, the marketing opportunities in the geolocation, post-map era are enormous. Forget all of those local merchants buying their way onto little squares of print advertising around the perimeter of the city grid. I never checked whether Florence had specific mapping apps, but the prospect for integrating walking tourists’ commercial wants and needs into a city-nav app is a no-brainer. The mobile moments come right after another: from toilet hunting to site directions, restaurant guides to finding some place to buy a Coke Zero for under 250 Euros.

Coming to rely on mobile gadgetry for tourist tasks follows a familiar pattern we have seen elsewhere in mobile media. Once you use and grasp the basic efficiency of mobile as a geolocation device, the gadget becomes your focus and you start wishing it could do even more. In the tourist-choked streets of Florence I was not in the position to search for a city-specific app to see if someone had already tried to make a live geo-guide to the city. I discovered later there were many mobile walking tours. I think like most travelers I used the tool that seems most familiar and obvious -- the embedded mapping and search (courtesy of Google for now) in iOS. It was serviceable, but all of the mobile search services have a golden opportunity here to grab the traveler at their first point of entry with more robust services before they find them elsewhere.

At one point plotting a journey across Italy, from our Tuscan villa to the family hometown on the Adriatic, Google suggested a two-day path that crossed the sea to Greece and ferried back to Italy’s east coast. Aside from that anomaly, the mapping was far and away the most accurate and successful resource we had to get us both in and out of towns and across neighborhoods. It beat physical maps and even a portable GPS loaded with international maps.

What was missing was greater intelligence about the mode of use and the user. The mobile experience needed shaping to tourist modes, moments and moods. To be sure, a next generation of tourist map will be a city-specific map, and some of these already exist. Within the narrower context of a tourist mode, certain kinds of otherwise intrusive and unacceptable marketing become welcome content.

Even more interesting to me is the truly personalized mobile travel app. What if my app really leveraged its knowledge of my tastes so that it could easily filter the endless possibilities of a place like Florence? Geo-triggered call outs on our device are the nightmare scenarios for many consumers concerned about mobile marketing. But when the user is in tourist mode, and the app is smart enough to know what would interest you, then push messaging from a geo-trigger is precisely what I want. A truly advanced and personalized geo-search engine would serve me, not the map. It would be able to accept my itinerary and keep me apprised of distance to sites or even to plot the most efficient paths. This is where mobile personalization, contextual awareness, marketing, and smartphone computing can overlap to genuinely enhance a time and place.

Physical context is only one piece of the mobile media puzzle. Mood and mode use will be the next layer of context that will help provide value to consumers and openings for laser-targeted marketing.

For international travelers, of course, all of this relies on affordable data service. That is another story altogether and another column. I am still waiting for the final bill. Talk about fear and loathing.