07/14/2014 11:56 am ET Updated Sep 13, 2014

A Portrait of Travel, from Kodak to Instagram

For a perfect symbol of how travel has changed over the last 20 years, I vote for that little cheese-yellow box of Kodak film. Oh, the debates we had about how many rolls of 24 or 36 exposures to cram into our bags. How we crossed our fingers every time we pushed the shutter button. And then came the antsy wait for the prints to come back from the drugstore. Subtract the rolls that didn't rewind right, the thumbs in front of the lens, the over-exposed sunsets, and you felt lucky to end up with a dozen or two really terrific shots.

These days, I'm giving in to the very American urge to do a then/now comparison because my own travel company, Classic Journeys, went into business almost exactly 20 years ago. Looking back, I sure wouldn't trade the speed, reliability and instant gratification of my digital camera for anything. The same goes for e-tickets. (Admit it: at least once in your life, you dumped a backpack or a purse onto an airport floor in the frantic search for a paper ticket that was actually in your jacket pocket.) Travel apps trump half-pound guidebooks full of slightly out-of-date info any day.

Way back in '95, your Bon Voyage party could tag along to the boarding gate at some airports... and you didn't take your shoes off until it was time to try sleeping on your overnight flight (in a seat with inches of width we've kissed goodbye forever). You couldn't go to Montenegro (because it didn't exist) or Myanmar (because nobody was allowed in). Somewhere in a drawer, you had an envelope full of leftover French francs that you couldn't use on your next trip to Italy or Spain. Vive l'euro!

You can probably add a dozen more changes to the list. But here's one you may not have thought about. In this flatter world -- where travelers swim in a sea of Wiki entries and crowd-sourced reviews -- it's gotten harder than ever to have the spontaneous, authentic experiences that are the Holy Grail of avid travelers. Is there a pho shop in Hanoi that hasn't been rated? An inch of the Inca Trail that hasn't been Instagrammed? A Croatian village that doesn't have its own website?

I call it the democratization of travel, and mostly it's an excellent thing. It opens minds to new ideas and inspires people to head for places they never considered before. But how crazy is it that the easier it becomes to research and travel to destinations, the harder it is to feel like you're able discover and be surprised by a place in a real, deep-in-your-soul way? Uncounted thousands have crossed Machu Picchu off their bucket lists in the last two decades, but how few of them got more than a quick, skim-the-surface visit?

This is where the job of travelers (and travel providers) has become extra challenging. We're well past the point of the kind of drive-by travel that was the norm for decades. Experiential is the new rule. If I have the option of making and eating pizza in a private Amalfi home on top of a cliff, I'll go for it every time over pizza in a ristorante. Introduce me to a truffle-hunter or a floating farmer in Myanmar or a cigar-roller in rural Cuba, and I'm a very happy camper. I love it when I can break down a barrier or shatter a preconceived notion. On a trip to Sardinia, I was lucky enough to meet a shepherd named Tonino. He made us lunch in his cottage, and we ate on cork plates in his garden. His only exposure to Americans used to be via SkyTV. Even mainland Italians are outlanders to him. My time with him showed me a world that I can barely believe still exists, but I like to think his eyes were opened in nice ways too. The urge to see the world this way -- and the growth of tour operators who are skilled in making it happen -- is one of the most interesting ways that travel has evolved in this new century.

Travel's democratization has also made a major difference in how we shop for and book vacations. Everybody has access to just about every pixel's worth of travel info on the Internet. In our own case, we started when websites were still optional. Our original site had a couple of dozen pages; we're up to thousands now. Google the phrase "Tuscany tour" and you get "about 15,500,000 results." You could book who knows how many hundreds of them with a couple of minutes at your computer keyboard... without ever exchanging words with another human. What hasn't changed is that travelers still love to talk -- about where they've been, where they want to go, the experiences they've had. Back in the day, those conversations happened most often with travel agents. That profession took a hit, first when airlines went direct to flyers and then as the Internet shouldered them aside. Though travel agents are staging a bit of a comeback now, there's still a deep urge -- and need -- to look under the hood of a travel option before you get your credit card out. Travelers now evaluate companies as much for the pre-trip info and consultation they get as for the actual vacation itself.

For us at Classic Journeys, the most recent change is that we're heading into our 20th Anniversary Year as the World's Best Tour Operator in the latest Travel + Leisure Reader Survey. Back in 1995, we couldn't have predicted that any more than we would have said we'd use our iPhone as a flashlight on an after-sunset stroll in a Croatian garden.

I'm just so happy that we've been here to see it all. That immersive experiential travel has grown to matter more than ever before. And that travelers who like to get under the skin of a place will go to whatever length it takes to make it happen. I'm not brave enough to predict everything the next 20 years will hold, but I'm willing to bet there will never be an app for that.