Colbie Caillat on "Breakthrough," Rob Thomas, Dave Stewart Tunes

Not many people manage to be productive while vacationing in Hawaii, but for Colbie Caillat — who wrote the tunes on her second disc, Breakthrough (out August 25th), in a rented house on Kauai's Hanalei Bay — relaxing doesn't equal slacking. "We'd go out boogie-boarding and then come back and write songs," says the singer, who honed the disc's mellow, beachy vibe with songwriter and American Idol judge Kara DioGuardi. "We just wanted to be inspired by everything."

Produced by her dad, Ken Caillat (who co-produced Fleetwood Mac's Rumours) the follow-up to Caillat's smash 2007 debut features acoustic tunes like the bouncy "You Got Me" (about a crush-worthy boy with a "crooked smile"), the anti-self-sabotage ode "Don't Hold Me Down," and the airy, Seventies-ish first single "Fallin' For You." The song is based on a real date Caillat went on with a dude who's now her friend. "I debated telling him it was about him, but I don't want it to be awkward," she says.

Caillat will bring her new tunes on the road when her U.S. tour — with opener Howie Day — kicks off on September 15th. "It's going to be low-key," says Caillat, who thinks she'll convince buddy Jason Mraz to drop in on a date or two. The set list isn't finalized, but Caillat promises tunes from her debut, Coco, as well as some covers: The Fray's "You Found Me," the Jackson 5's "I Want You Back" ("I used to sing it live, but I took it out of the set," she says. "When Michael Jackson died, I put it back in.") Caillat is also squeezing in an unlikely track: "Don't Cha," by the Pussycat Dolls. "We slow it down so it's really soulful, like a Marvin Gaye-type feel," she says. "It's a really sexy vibe."

Stay tuned for more new Caillat songs: the singer plans to release tracks she cut with Rob Thomas (called "Still in Love") and the Eurythmics' Dave Stewart ("Bulletproof Vest") in the future. "They'll definitely see the light of day," says Caillat, who's especially psyched about her collaboration with Stewart. "It has this crazy intense violin solo and lyrics like, 'Take off your bulletproof vest and let me in… I won't make you bleed," she says. "It's different than any song I've ever done before — very adult stuff."

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Song Stories

“All Along the Watchtower”

The Jimi Hendrix Experience | 1968

Jimi Hendrix got hold of Bob Dylan's early John Wesley Harding tapes and in late 1967 recorded a version of "All Along the Watchtower" with the Experience in London. Dissatisfied with that first development, Hendrix brought those tapes with him to New York in early 1968 when he began work on Electric Ladyland. Eddie Kramer, Hendrix's engineer at the time, told Rolling Stone that Hendrix "was still looked upon by his basically white audience as the mammoth black guitar hero. There was a constant fight within him to expand himself." Hendrix's successful take on Dylan's work has long been recognized by the songwriter. "I liked Jimi Hendrix's record of this and ever since he died I've been doing it that way," Dylan wrote in the liner notes to his Biograph box set. "Strange how when I sing it, I always feel it's a tribute to him in some kind of way."

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