Benchmarking is essential for developing destinations to improve and develop their service delivery. Croatia is a well-established summer tourism destination, but more remote (inland) destinations seek to increase their competitiveness to help sustain Croatian tourism year-round—to diversify tourism offerings beyond the (more traditional) sea and sun opportunities. Expanding Croatia’s tourism offer will require additional investments, not only in coastal destinations but in rural continental areas as well. Looking at how more established rural and winter destinations are planned and managed, this paper seeks to discuss how Croatia can learn from its neighbour Slovenia which has well-established winter sports destinations (in rural areas). This is where a benchmarking approach, building on a comparative analysis conducted through fieldwork research contributes new insight. Research was conducted in both Pokljuka (Slovenia) and Gorski kotar (Croatia) between 2015 and 2017. Three different procedures were used to collect data: (1) documental research of the destinations, facilities and events, (2) on site visits involving qualitative interviews and conversations with key stakeholders and (3) direct observation of the destination while attending events. Three emergent themes best reflected the analysed insights from the data collection: infrastructure, business operations and community involvement/stakeholder participation. To assess different points of service offering and delivery, discussions in Pokljuka were framed around sports tourism opportunities and their established business models to understand planning, management, organisation and service delivery. These same three points are then discussed as opportunities for Gorski kotar. To reiterate the benchmarking focus, first research must present a comparative analysis and then put emphasis on planning and managing service delivery to help highlight how insight from a well-established destination informs emerging destinations with tourism potential.