Approaches
The steep rocky character of Marblehead's harbor also defines the entrances. Deep channels make their way past bold islands and extensive outlying ledges.
From the south, Marblehead Channel is wide and unobstructed. The red and green bell at the mouth, flashing (2+1) red, is quite bright, usually visible 3 miles off. To the east, the intricate channels criss-crossing Salem Sound appear more obvious on the chart than they do from the cockpit. Most of the rocks are marked, though many of the marks are unlit, making this area somewhat inimical to exploration at night.
Anchorages
Anchoring is neither practical nor permitted in Marblehead harbor.
Moorings
Marblehead harbor is open to the northeast, and gets pretty wild in a coastal storm, with moored boats heaving up and down in 2-3 foot seas. In normal summer weather it's quite pleasant. Salem Sound is bothered by a persistent groundswell, though, seemingly no matter what the weather. So boats moored near the harbor mouth should expect to roll a little.
Most guest moorings are administered by the three major yacht clubs. Eastern and Corinthian are both located on the Neck; their launches can take you to the clubhouse or to town. The Boston clubhouse is on the mainland side, in the old town.
The Harbormaster may also be able to find you an empty mooring.
Marblehead has lots of moorings, and just as many boats. Odds are usually pretty good that something is available, but avoid the time before the Marblehead/Halifax Race (odd years, early July), during Race Week (usually late July) and any of the big regattas that Marblehead regularly hosts.
Slips
Tie-up space is extremely limited in Marblehead. The Harbormaster does have a few hundred feet of floating dock, just past the Town Landing. It's conveniently right in town, and space can be reserved. But it is subject to the same uncomfortable roll from the north and east as the moorings, and becomes untenable in even a near-gale from that quarter. Tuckers Wharf Dockage Policy (pdf from town website).