Players step into the shoes of series protagonist Kraft Lawrence on his adventures with Holo. Traveling north to find information about Holo's hometown, the two are confronted by a huge water channel that they cannot cross without going through strict identity checks, impossible for Holo at the ears of wolf. In search of an alternate passage, they encounter the game's original character Luka, daughter of a smuggler who is currently missing.

Like the first game, the gameplay involves traveling through various locations, trading goods, and making the right choices during romantic events. There are also various new and improved mechanics, such as the inclusion of contracts with strict delivery times and a grid-based inventory system.

Also new is the inclusion of a third character to travel with, allowing players to choose between deepening their relationship with Holo or another heroine of their choice. Possible companions include Norah, a shepherd; Eve, a merchant whose skills are said to surpass those of Lawrence; or the new character Luka.

Completing all four character routes on the same save slot unlocks "Endless Mode" which provides a new post-game quest with no time limit.