In late September, early October things are a bit slower as the summertime family crowds have gone home to get the kids in school. Nonetheless, if those are important activities for you, go ahead and book your reservation in advance so you are sure you don't miss out.
You are wanting to do the ferry to Lanai and explore on your own? You may not need to worry about the ferry, but if you are wanting to rent a vehicle there, they are limited in numbers! Not sure how busy they would be, given the time of year, but something to consider.
On the other hand, if you are just going to wander over to Manele Bay and spend the day snorkeling, I wouldn't worry about it.
We booked the ferry 1 week before we wanted to go (you can only book on-line).
We had already taken the day tour to Lanai via Trilogy (which was awesome), but wanted to spend more time at Hulopoe Bay. It is only a 10 minute walk to the beach from where the marina is located. We did carry our gear, but enjoyed a fabulous day!
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