This paper presents the development and validation of a novel multi-sensory wearable system (Personal Automatic Cigarette Tracker v2 or PACT2.0) for monitoring of cigarette smoking in free-living conditions. The contributions of the PACT2.0 system are: (1) the implementation of a complete sensor suite for monitoring of all major behavioral manifestations of cigarette smoking (lighting events, hand-to-mouth gestures, and smoke inhalations); (2) a miniaturization of the sensor hardware to enable its applicability in naturalistic settings; and (3) an introduction of new sensor modalities that may provide additional insight into smoking behavior e.g., Global Positioning System (GPS), pedometer and Electrocardiogram(ECG) or provide an easy-to-use alternative (e.g., bio-impedance respiration sensor) to traditional sensors. PACT2.0 consists of three custom-built devices: an instrumented lighter, a hand module, and a chest module. The instrumented lighter is capable of recording the time and duration of all lighting events. The hand module integrates Inertial Measurement Unit (IMU) and a Radio Frequency (RF) transmitter to track the hand-to-mouth gestures. The module also operates as a pedometer. The chest module monitors the breathing (smoke inhalation) patterns (inductive and bio-impedance respiratory sensors), cardiac activity (ECG sensor), chest movement (three-axis accelerometer), hand-to-mouth proximity (RF receiver), and captures the geo-position of the subject (GPS receiver). The accuracy of PACT2.0 sensors was evaluated in bench tests and laboratory experiments. Use of PACT2.0 for data collection in the community was validated in a 24 h study on 40 smokers. Of 943 h of recorded data, 98.6% of the data was found usable for computer analysis. The recorded information included 549 lighting events, 522/504 consumed cigarettes (from lighter data/self-registered data, respectively), 20,158/22,207 hand-to-mouth gestures (from hand IMU/proximity sensor, respectively) and 114,217/112,175 breaths (from the respiratory inductive plethysmograph (RIP)/bio-impedance sensor, respectively). The proposed system scored 8.3 ± 0.31 out of 10 on a post-study acceptability survey. The results suggest that PACT2.0 presents a reliable platform for studying of smoking behavior at the community level.