Yes Man - Danny Wallace (Not much travel, but same feel as Tony Hawk's "round Ireland", and it's currently being made into a movie - read it now and impress your friends with how much of a hipster you are.)
An Embarrassment of Mangoes: A Caribbean Interlude - Ann Vanderhoof (Not very funny, but entertaining. Wife and husband rent out their house, and then sail from Toronto down to the top of South America. Really good read for the summer if you're on a beach)
Books that aren't out yet, but that I plan to pick up soon in this vein: America Unchained - Dave Gorman (Ok, so it came out a month ago, but I haven't yet picked it up. Also check out his Googlewhack Adventure book for a funny travelogue)
Friends Like These - Danny Wallace (The new book from the author of Yes Man - He tracks down his childhood friends all over the globe, and invites them outside to play. It looks brilliant!)
Fantastic question! I'll be following this one closely. posted by xotis at 2:25 PM on June 5, 2008
PJ ORourke's Holidays in Hell is okay. posted by ROU_Xenophobe at 2:29 PM on June 5, 2008
Eat Pray Love (Liz Gilbert) is sortof a travel book, 50-50 interior/exterior traveling but it's lots of fun. posted by dancestoblue at 2:33 PM on June 5, 2008
Not quite in the same vein, but I can't resist recommending it: The Clumsiest People in Europe. I stumbled upon it by accident a few years ago in the travel section at a bookstore and, between collapsing on the floor in hysterics and eventually whimpering in pain from the strain of all the laughter, made a little bit of a scene. It's a little like Dick Cheney got a sex change, then commandeered a time machine and set the dials for the 19th century: "The Spaniards are not only idle, they are very cruel.... The country is full of robbers and wolves." posted by scody at 2:37 PM on June 5, 2008
I've always been a fan of Mark Twain's "The Innocents Abroad". Granted, I was and still am a huge Twain fan, but it was hilarious when I first read it in the 7th grade and got more hilarious each time I'd read it over the passing of time because I'd uncover a new detail of sarcastic wit I didn't quite get when I was younger. posted by kkokkodalk at 3:00 PM on June 5, 2008
Oh, there was a book a while back, 'The Jaguars Teared My Flesh' or something. I read it but don't remember the author or, indeed, the title, but it was pretty funny and there was some travel in there. posted by turgid dahlia at 3:11 PM on June 5, 2008
Redmond O'Hanlon is a great travel writer. He's written a few books, but my favorite is Into The Heart of Borneo. He and his buddy, both older, overweight and totally NOT your typical bushwhacking enthusiast, stumble their way through the jungles of Borneo. The scene when he discovers with great horror that the bowl of spaghetti he's eating is indeed a bowl of um, worms, is one of the funniest scenes I've ever read. posted by HeyAllie at 3:31 PM on June 5, 2008
I'm reading Holy Cow by Sarah McDonald right now. It shows some harrowing moments, but it's very funny. posted by Countess Elena at 5:40 PM on June 5, 2008
A Movable Thirst. The tale of two guys, one a wine novice and one not, who visit every winery in the Napa Valley. posted by SoftSummerBreeze at 7:56 PM on June 5, 2008
It is a travel guide, but not to an actual place. It is supremely hilarious
Another vote for The Clumsiest People in Europe, an amazing, hilariously judgmental book from a bizarre early 19th century children's book author. I laughed so hard just reading the table of contents and introduction I had to put it down, and had other people in the room asking if I was ok and what the hell was I reading, anyway? The fact that such a bigoted, ignorant but weirdly captivating book was originally meant for children is what really gets you. But yeah, the last book I laughed so hard at was 'Round Ireland with a Fridge. posted by mediareport at 8:40 PM on June 5, 2008 [1 favorite has favorites]
The work of Tony Horwitz is quite good. Blue Latitudes (published under other names as well) is about his following the route of Captain Cook and is engaging and funny.
I second Redmond O'Hanlon although I think No Mercy is his best.
Also, shameless self-promotion, my article Vampires from Venus won the SOLAS Award for funniest travel writing of 2007. posted by xz at 9:55 PM on June 5, 2008
Seconding Molvania. And it's great to leave out on a table and watch your friends pick it up with no explanation. posted by lpsguy at 5:59 AM on June 6, 2008
I'm reading Lost on Planet China right now -- it's good. You'll like it.
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It's a good thing you specified non-fiction or I'd be suggesting Terry Pratchett.
posted by tkolar at 2:15 PM on June 5, 2008