Lonely Planet, best known as a traditional travel guidebook publisher, is announcing a new U.S. head tomorrow–John Boris of Zagat Survey–as it increasingly moves to reposition the company as much more of a “cross-media” platform.

As the paid versus free content online debate gets louder over the next year, how well known brands like Lonely Planet–which has a strong reputation among consumers–handle the fallout will be more and more interesting to watch.

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Let’s all agree first to blame owner Condé Nast for deciding to shutter Gourmet–the elegant and iconic magazine, which has been around since 1941, after the November issue.

While circulation remained steady at Gourmet at just under one million monthly paying subscribers, Condé Nast Chief Executive Officer Chuck Townsend pointed to a fall-off in advertising spending by luxury brands that result in a money-losing mess.

But some are blaming a movement of readers to the Web. Is it true?

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Back in April, Tim Armstrong sent a memo to the long-battered troops of AOL about a 100-day vision quest the new CEO and chairman was going on to find out “how to bring back the magic of AOL.”

It is now Day 86, and Armstrong is closing in on the end of a Where’s-Waldo commitment that he made then to visit all of the far-flung offices of the Time Warner online unit globally to find out what’s what and what he should do to turn AOL around.

BoomTown is eager to see what Armstrong has found out on his trip and what path it will ultimately put AOL on.

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Yesterday, BoomTown wrote that Yahoo’s SVP North American Audience, Jeff Dossett, was leaving the Internet company after a very short stint there, because of personal reasons.

But I also noted that sources said he was likely to quickly land at a start-up, and in fact, he has resigned from Yahoo to do just that.

Dossett, who came to Yahoo from Microsoft in November, is taking a job as CEO of AdventureLink, an online site aimed at adventure travel and booking such trips.

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This week, I went on a trek to downtown San Francisco–from ATD HQ, located in the wilds of the Castro–to visit David Sifry, the jovial Web entrepreneur who recently launched Offbeat Guides.

The San Francisco-based start-up makes “personalized, up-to-date travel guides that cover over 30,000 travel destinations, using a combination of search technology and curation by both amateur and professional travel experts.”

In other words, on-demand travel books with a touch of humanity.

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