The player character begins Dear Esther standing on a pier, facing the lighthouse. The lighthouse with its associated outbuilding have both been abandoned and are in a state of disrepair. The staircase up to the top of the lighthouse has collapsed, making ascent to the top impossible.
Past the lighthouse is a path leading through the cliffs and a beach. There are several items of interest on the beach, including a Fibonacci Spiral (also see Golden Spiral) carved into the sand, and several assortments of car wreckage. Off in the distance is the glowing red light of the island's radio mast and a cliff with white lines carved deep into its side. The path leads further inland, towards the second level.
The story beings with the narrator introducing the player to the location, that is, a Hebridean island. The narrator begins speaking a letter to "dear Esther". There are two different dialogues that can occur, one talking about the island as a mystical place 'birthed' by the author, and one outlining the island's history as written by Donelly, an 18th century author. As the player follows the various paths in this segment, more is divulged, both about the island's diseased history and the mental state of the narrarator. As the player comes to the end of the chapter, the narrator mentions Paul, Damascus and a fateful visit.
Another important mention made in this segment is that of the hermit. Written about by Donelly, the Hermit was holy man who, legend has it, came to the island in a boat without a bottom "so that the creatures of the sea could come and converse with him". The Hermit lived in the caves of the island, and the narrator claims to have found his bones and hidden them away. The idea of a boat without a bottom becomes very important throughout the storyline.
This plays as Chapter 1 opens.
- Dear Esther. The gulls do not land here anymore; I've noticed that this year, they seem to shun the place. Maybe it's the depletion of the fishing stock driving them away. Perhaps it's me. When he first landed here, Donnelly wrote that the herds were sickly and their shepards the lowest of the miserable classes that populate these Hebridean islands. Three hundred years later, even they have departed.
- Dear Esther. I sometimes feel as if I’ve given birth to this island. Somewhere, between the longitude and latitude a split opened up and it beached remotely here. No matter how hard I correlate, it remains a singularity, an alpha point in my life that refuses all hypothesis. I return each time leaving fresh markers that I hope, in the full glare of my hopelessness, will have blossomed into fresh insight in the interim.
- Dear Esther. I have lost track of how long I have been here, and how many visits I have made overall. Certainly, the landmarks are now so familiar to me that I have to remind myself to actually see the forms and shapes in front of me. I could stumble blind across these rocks, the edges of these precipices, without fear of missing my step and plummeting down to sea. Besides, I have always considered that if one is to fall, it is critical to keep one’s eyes firmly open.
- Dear Esther. The morning after I was washed ashore, salt in my ears, sand in my mouth and the waves always at my ankles, I felt as though everything had conspired to this one last shipwreck. I remembered nothing but water, stones in my belly and my shoes threatening to drag me under to where only the most listless of creatures swim.
- The first of all ghosts can be found transparently rushing past the window of the outbuilding as you approach it, and occasionally at the top of the lighthouse staircase.
- The levels file in the maps folder is named 'Donnelly'.