Two years ago, Tod Breslau and Kelsey Bunker -- armed with a precise vision and “a lot of balls,” as Breslau, a real-estate developer, puts it -- purchased a rundown, prostitute-friendly Travel Inn in a dodgy part of town, and transformed it into the Jupiter Hotel, Portland’s beacon of cutting-edge design and indie cool. Located in the newly-hip “LoBu” area, the 80-room retreat features wall-size photoscapes, slate chalkboard doors, a communal fire pit, and Doug Fir -- a swanky, Alpine-style restaurant/rock venue where you can have venison tenderloin while watching Nouvelle Vague perform. And it all costs around $100 a night. (To keep its former lecherous spirit alive, the hotel also offers an “After Midnight” rate of $59.)

Last year, Conde Nast Traveler put the Jupiter on their “Hot List,” and ever since, people have made pilgrimages to Portland solely to stay at the hotel. Like Jenna Bush, who, on a recent road-trip with her boyfriend, made a pit-stop in the city specifically to shack up at the hotel for two nights. “It was pretty funny,” tells Breslau. “Her Secret Service came in ahead of time dressed like Gen-Xers in jeans and hoodies.” But of course, there is more to Portland. Here, Breslau explains what: 

Powell’s City of Books
“It’s universally recognized as the best bookstore in the country. It’s an institution, and it’s only in Portland. The headquarters location, called The City of Books, is enormous. It’s four stories, piles of books. Any book you’d ever want you could find there.”

Apotheke
“It’s ‘apothecary’ in Greek and it looks like the Milk Bar from A Clockwork Orange. It’s a ‘neat bar,’ meaning there are no mixers. You can’t get a Rum and Coke, but you can get all kinds of exotic liquor on the rocks, neat, as a shot.”

The Galaxy
“It’s real down-and-dirty. It’s an old Denny’s turned Chinese restaurant turned karaoke bar. It has ‘60s diner booths and bubbly water with dirty fish, and it’s filled with pierced and tattooed people. It’s like something out of a Tarantino movie.”

The Screen Door
“A young couple from Portland opened it about a month ago. They’re doing nouveau Cajun cuisine, like tempura fried chicken, and they make these beautiful beignets. It’s become an overnight sensation.”

Clarklewis
“They turned this huge industrial loft space that’s right on a loading dock into a restaurant. It has gigantic open ceilings and rolling garage doors. And the kitchen and dining area aren’t separated, so you’re basically eating amongst the chefs. It’s like The Cook, the Thief, His Wife & Her Lover.”

The Hawthorne District
“It’s sort of Berkeley-meets-Melrose. It’s a little hippie, a little design, a little fashion. It’s one of the few shopping areas that’s always alive. Le Rouge is a great store in the area that sells women’s designer clothes and great jewelry. It’s really groovy. My girlfriend owns it, so I have to give props.”

The Red Light
“They have new and vintage clothes. Great ties, blazers and tailored shirts. It’s a killer store.”

Go There:

Powell’s City of Books, 1005 W. Burnside St, (503) 228-4651; powells.com

Apotheke, 1314 NW Glisan, (503) 241-7866; apotheke-nw.com

The Galaxy, 909 E. Burnside St., (503) 234-5003

The Screen Door, 2337 E. Burnside, (503) 542-0880

Clarklewis, 1001 SE Water Ave, (503) 235-2294

Le Rouge, 3418 SE Hawthorne Blvd, (503) 230-8119

The Red Light, 3590 SE Hawthorne Blvd, (503) 963-8888 

Get A Room: 

The Jupiter Hotel, $89-$119/night. “After Midnight” rate, from $59, based on availability. 800 E. Burnside, Portland; (503) 230-9200, jupiterhotel.com,

The modern art fair, Affair, takes place at The Jupiter Hotel, September 29-October 1, 2006. For more info, affair-jupiterhotel.com

Munch on venison tenderloin while watching Nouvelle Vague perform at Doug Fir, dougfirlounge.com

Apotheke photo courtesy of Wolfchoir, flickr.com/photos/poopfilter/

Galaxy Bar photo courtesy of TristanT, flickr.com/photos/mediahound/