After being dropped by Verve, the band signed to Decca Records, where they released their most critically acclaimed album, In the Land of Grey and Pink, in 1971.

[8]: 3 After a series of gigs in London, including the Speakeasy Club, the band were introduced to Terry King, who became the group's first manager.

David Hitchcock, who had been working in the art department of Decca Records, asked the company's president, Hugh Mendl to sign the band.

[8]: 4  They began recording their second album, If I Could Do It All Over Again, I'd Do It All Over You (1970) in September 1969, while continuing to gig on the university circuit, and appearing at festivals alongside Pink Floyd, Yes, The Nice and Soft Machine.

[9]: 4  The accompanying single "Hello Hello" helped them land an appearance on the TV show Top of the Pops, performing the album's title track.

[9]: 8  The group decided to follow up "For Richard" with a suite of short sections of songs written by David Sinclair, that the rest of the band worked on and linked together to form a side-long track, "Nine Feet Underground".

In August 1971, David Sinclair accepted a job with former Soft Machine drummer Robert Wyatt's new band, Matching Mole.

"[12]: 10 Hastings and Coughlan decided to continue as Caravan, and the duo recruited viola player Geoffrey Richardson, bassist Stu Evans and keyboardist Derek Austin and toured extensively.

[1] The resulting album For Girls Who Grow Plump in the Night (1973) was a major critical achievement[1] and showed that the group could survive the loss of co-vocalist Richard Sinclair.

Jimmy Hastings reprised his role as orchestrator along with Martyn Ford and John Bell,[13] while the Soft Machine's Mike Ratledge contributed an instrumental piece, "Backwards" as part of a medley.

[14] The group followed this with a live album, Caravan and the New Symphonia (1974), including orchestral arrangements by Ford[15] and conducting by Simon Jeffes.

They have also achieved steady sales and a fan following with the support of Stuart Maconie' "Freak Zone" show on BBC 6 Music.

[18] After performing at NEARFest in 2002,[14] they released The Unauthorized Breakfast Item album in 2003, where David Sinclair was replaced by a returning Jan Schelhaas.

[18] In 2010, Pye Hastings announced that the band had resumed activity in anticipation of a one-off concert recording at Metropolis Studios for ITV, which took place in December 2010.

[20] In January 2013, the band completed a successful UK tour to celebrate the 40th Anniversary of the album For Girls Who Grow Plump in the Night (1973).

[26] Following Sinclair's departure, the musical direction has been predominantly led by Pye Hastings, who preferred a softer pop rock approach.

[14] Though the group share a common history with Soft Machine, they have been considered more melodic and closer to folk music[27] and frequently displaying a sense of humour.