Approaches
Sailing across Nantucket Sound is the perfect prelude to the island itself. It's over 20 miles from either Hyannis on the Cape or Edgartown on the Vineyard, so the low shores on either side disappear in even the lightest afternoon haze. First the big tank west of town, and then the landmass of the island rises ahead. In a good summer southwester the ride gets bumpy enough to be exhilarating. Making the passage, short as it is, adds substantially to Nantucket's defining sense of remoteness.
The proposed wind farm on Horseshoe Shoal, for all its worthy environmental contributions, seems sure to transform the Sound from the island's wild preface into a mere obstacle. "Nantucket? Yeah. Go past the windmills, first harbor on the right. . ."
The harbor entrance is flanked by jetties extending almost a mile into the Sound, and the dredged channel is marked by a string of nuns and cans. It's wide enough that you may have room to maneuver under sail, but it's also heavily travelled by recreational boats and the island's many ferries.
Anchorages
You can generally anchor inside, to the north and east of the mooring area. Watch the depths; there's a large shoal area in the middle of the harbor. Any anchorage will be even farther from town than the moorings. And the harbor is big enough that there's an appreciable fetch, especially from the east.
Moorings
Nantucket Moorings maintains over a hundred moorings in the harbor for transients. They accept reservations, but require a 2 or 3 night minimum for reserved moorings. Out of season, it's a good bet you can get an unreserved mooring on a first-come first-served basis, but reservations are recommended between late June and Labor Day. See the reservation form on their website.
It's worth noting the harbor is big enough that the moorings can be pretty far from town. Launch service is available, but it's not included in the mooring fee, and the launch charges per person, per ride. So if you have a poor-rowing dinghy with no outboard, or a big crew that wants to visit town repeatedly, you can end up spending more on launch rides than the (not inconsequential) cost of a slip.
Slips
Slips are available from the Nantucket Boat Basin, located on the western shore of the harbor and right downtown.
The Boat Basin is a quintessential full-service marina, with a concierge who can seemingly arrange anything, including on-board spa service. A member visiting recently tells of the dock staff's slightly incredulous reaction when he assured them he didn't need to plug into shore power, cable TV, or high speed internet.
But seriously, TV hookup or not, the Boat Basin staff in our experience is unfailingly welcoming and helpful.
Reservations
Demand for both moorings and slips in Nantucket harbor is highly seasonal. The Boat Basin sends reservation forms to their mailing list in January and popular dates fill quickly. In early June, they may not answer the radio after 5pm, and following Labor Day, you can pay for two nights and get a third free.