I have never been there, so I would love any information anyone can give me.
What timeshare there is the best?
All 3 are nice and very different. It depends if you want to be far out from Nantucket town (Tristram's), a short walk to town (Brant Point Courtyard), or right in the heart of town (Mariner House).
You would definitely need a car if you stay at Tristram's in October as the shuttle is not running then. No car necessary at BPC or MH, however the units are much smaller. I've stayed at all 3 and like each place.
I think we will want to take the ferry, so where should we fly into?
You could fly into Boston, MA, Providence, RI, or Hyannis, MA.
Is October too chilly?
Probably too cool to swim, but the weather is usually quite pleasant this time of year, and great for bike riding.
What do you like to do on Nantucket?
Walk the beaches, eat, stroll around town, but mostly bike ride. The paths are wonderful and take you all over the island.
Do they rent golf carts for the week to explore the island?
No, but you can rent Mopeds and all kinds of bicycles.
Grocery stores? Or should we shop b4 getting on the ferry?
I usually take frozen meats and other items with me, but also shop at the Grand Union market on the island. Prices aren't really too bad off season.
Go to
www.nantucket.net and
www.nantucketchamber.org for lots of information about the island including events, dining, and car and moped rentals. Nantucket Island is my favorite place!