- Gentleman's Bluff has historically been quite a queer haven, at times a sleepy, friendly little community, at other times a bustling center of witchcraft, and it has recently become more prominent as a tourist destination.
- The first known settlement on Gentleman's Bluff was founded by Captain Montague Locke when his ship wrecked against the island's eastern shores. It was noted as an especially gentle shipwreck, and he wrote in his journal that it was "as if the island were welcoming us home."
- The island is heavily wooded with a mix of pines and oaks. The northern end tends to feature mainly pines, while the south is mainly oaks.
- The southern shore also features low cliffs, the western higher cliffs, while the north point is the highest, and the eastern side of the island, perhaps worn down by more exposure to stormy seas over long years, features more sandy beaches.
- The island's highest north point is the site originally called Gentleman's Bluff, where an ancient lighthouse still stands.
- The Coven Oaks area, near the island's southern point, is widely believed to have historically been home to an unusually large population of witches. It is known for especially enthusiastically embracing Halloween, with nearly every one of its varied styles of residences tending to enthusiastically decorate for a traditional harvest and spooky season.
- Eros Hollow is the most solidly residential and middle class area of the island, as well as its most inland and low-lying point.
- Marin Cliffs is mixed light residential and commercial, with picturesque views atop the cliffs that overlook the Atlantic between the island and the mainland.
- Los Fuentes is home to the grand Beaumont Hall and the picturesque old wooden covered bridge across Gladmead Creek.
- Port Jolly Roger is home to a number of beaches, boardwalks, and other attractions, including many shops and the pleasure pier. Nearby, one can also find the historic Old Graves Cemetery and the Ocean View Social Gardens, which are more commonly just called "The Park."
Points of Interest
The following locations are points of interest in Gentleman's Bluff:
