You are given many options while you're on the island. Most of your choices can be divided into three major categories: dating, building group morale, and searching for clues. Your actions will not only affect the ending of your game, but also the outcome of many of the characters in the story. There are five other students and a teaching assistant staying on the island. Without your intervention, not all of the characters will survive. The students have their own fears, suspicions, and motives. Understanding them is the key to helping them and directing suspicion away from you. But be careful who you befriend -one of the characters might be the killer.

You have the option to date three of the students: Matt, Carl, or Ray. Dating one of these students will lead you on various routes through the story. There is also a no romance route where you can befriend one of the characters. In most cases when you choose an option for someone's romantic route, a heart is shown in the upper right corner of the screen to show which character liked your decision. However, no hints are given when you try to befriend a non-datable character, so it's hard to know if you made the right choice.

It can be difficult to balance dating a character, dealing with group morale, and searching for clues. Going for a date might mean missing an event that will affect the life of a friend. Not dating might mean not getting the ending with the character you want. If you spend all of your time searching for clues you might miss both.

Pinewood Island has interesting sprite art and gives you the option to customize your character at the beginning of the game. You can choose your character's name, skin-color, outfit, and even hair highlights. The sprite art is unique, and the character emotions are well done. However, there are different art styles for the sprite drawings and the CG's, and sometimes the difference in style can be jarring.

Some of the game altering events are very specific and can be hard to figure out. A few lines from your character might affect the outcome of the entire game. Your character will have to make decisions constantly and it's hard to weigh which ones were the most important. While having three different elements of decision making makes the game complex, it does keep the story interesting. If you make the correct choices, you may figure out who the killer is on your first few gameplays. How to bring that character to justice is a different story.

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