Abstract: A cigar-cooling ashtray system is configured for cooling a lit cigar between puffs, preferably to keep at least a body length of the cigar in an ambient temperature range around 65-70 degrees Fahrenheit. The system includes an upper unit with a central ash receptacle and a raised rim around the central ash receptacle, where at least one thermally-conductive region of the raised rim is lower than a tallest portion of the rim and is positioned and contoured to hold and maintain sufficient surface contact with the cigar to keep its lit end suspended above the central ash receptacle. A base comprising at least one cooling chamber is removably attachable to the upper unit, where the cooling chamber is in thermal communication with the thermally-conductive region of the raised rim when the base is attached thereto. An attachable/removable secondary base may be included to provide storage and/or aesthetic enhancement.