We report an all-polarization-maintaining fiber optic approach to generating sub-2 cycle pulses at 2 {mu}m and a corresponding octave-spanning optical frequency comb. Our configuration leverages mature Er:fiber laser technology at 1.5 {mu}m to provide a seed pulse for a thulium-doped fiber amplifier that outputs 330 mW average power at 100 MHz repetition rate. Following amplification, nonlinear self-compression in fiber decreases the pulse duration to 9.5 fs, or 1.4 optical cycles. Approximately 32 % of the energy sits within the pulse peak, and the polarization extinction ratio is more than 15 dB. The spectrum of the ultrashort pulse spans from 1 {mu}m to beyond 2.4 {mu}m and enables direct measurement of the carrier-envelope offset frequency using only 12 mW, or ~3.5 % of the total power. Our approach employs only commercially-available fiber components, resulting in a turnkey amplifier design that is compact, and easy to reproduce in the larger community. Moreover, the overall design and self-compression mechanism are scalable in repetition rate and power. As such, this system should be useful as a robust frequency comb source in the near-infrared or as a pump source to generate mid-infrared frequency combs.