Lanai is laid back and has a much smaller population than the other islands. The airport only supports inner-island flights. Since I only spent a day there (ferry from Maui) I can't provide much content on it. If you're a public figure (celebrity, well known athlete, public figure) who values privacy, I presume this is the place to go. The snorkeling at Hulopoʻe Beach Park was amazing and worth the trip. What I saw of The Four Seasons while grabbing breakfast was over-the-top
Due to the difficulty of reaching Lania and the sense of remoteness, you may get the feeling that people there aren't welcoming of tourists. In my experience, nothing could be further from the truth. The people where super-friendly and welcoming.
We took a van to Lanai City, had lunch, and did a bit of shopping at the boutique shops (bring cash if you visit Lanai). Lanai City feels like you're in the mountains somewhere - it doesn't feel like Hawaii.
Maui | The Big Island | O'ahu | Kauai | Lanai