Approaches
The entrance to Vineyard Haven is a mile wide, with deep water right across. Prominent lights mark both of the flanking headlands - East and West Chop. Note that the current rounding West Chop is the strongest of any in Vineyard or Nantucket Sounds, topping 3 knots on a big tide.
Anchorages
Anchor outside the breakwater, staying clear of the mooring field, and well clear of the fairway. Ferries transit the harbor at least hourly from 6 am to 11 pm. If you're anchoring early in the season before all the moorings are in, a tripline on your anchor is good insurance against old mooring gear on the bottom.
Moorings
Town moorings inside the breakwater are first-come first-served. Call the Harbormaster.
Outside the breakwater are privately maintained moorings, available through either Vineyard Haven Launch Service or Vineyard Haven Marina. At least some of these may be reserved.
Moorings fill up throughout the summer.
Slips
Vineyard Haven Marina and Black Dog Wharf are the primary sources of transient slips. Tisbury Wharf Company may also have tie-up available.
When all private slips are full, the Harbormaster may use the Town Dock for overnight stays. Otherwise it is used for pickup/dropoff and hourly tie-up.
Storms
Because the harbor is quite exposed from north to northeast, the anchorages, outer harbor moorings and even some slips are vulnerable to severe weather from that direction. Given the limited space behind the breakwater, Vineyard Haven is a poor refuge in a northeast gale.