The article offers the authorial methodology for assessing the digitalization level of travel agencies. The relevance of creating a specialized assessment tool that takes into account the limitations of small businesses and the customer-oriented nature of travel services is substantiated. A system of 25 indicators has been developed and grouped into six areas: operational automation, online sales, marketing, security, IT competencies and integration with government platforms. A method for calculating an integral indicator of the digitalization level using a matrix of indicator significance and a 100‑point scale is proposed. The methodology was tested on a sample of 15 small travel agencies in Moscow, which made it possible to identify typical “blind spots” of digitalization and identify priority development areas. As a result, a pronounced polarization of the industry has been revealed: the gap between technology leaders (online aggregators) and traditional travel agencies exceeds four times the value of the integrated Digital Maturity Index (DMI). Based on empirical data, the hybrid model (Phygital) is substantiated as the most promising for small and medium-sized businesses, allowing small and medium-sized enterprises to increase operational efficiency while maintaining the competitive advantages of personal service. Integration with government platforms and marketing automation are recognized as priority development areas. The developed methodology can be used by owners of small tourism enterprises for diagnostics, digital transformation planning and benchmarking.