Penobscot Bay

Day 1: Pulpit Harbor

Distance: 8 to 10 nm

If there’s a quintessential anchorage in Maine, it’s got to be Pulpit Harbor.  An easy sail in most conditions from the mainland, with excellent sunsets and some room to anchor. 

Alternate harbors: Warren Island or Cradle Cove are about the same distance if it’s peak season or you get a late start.

Day 2: Perry Creek, Vinalhaven

Distance: 10 nm

Gorgeous well-protected anchorage dominated by moorings, within easy dinghy distance of North Haven village. Be sure to make a reservation at Nebo Lodge for dinner!

Alternative harbors: Carver Cove is a little quieter 2 nm further and Seal Bay is further at 7 nm.

Day 3: Bold and Devil Islands, Merchants Row

Distance: 12 nm

Bold and Devil Islands lies in the middle of the spectacular, granite-encrusted island collection along Merchants Row.  

Alternative harbors: McGlathery in Merchants Row or Southeast Harbor on Deer Isle.

Day 4: Torrey Island, Eggemoggin Reach

Distance:  10 nm

Torrey Island offers a large secure anchorage in most conditions, wooden boat eye candy everywhere you look and island access and beach.

Alternative Harbors: Babbidge Island (Wooden Boat School) or Benjamin River

Day 5:  Holbrook Island

Distance: 17 nm

Holbrook Island has wonderful hiking, is well protected and you might even find a free guest mooring.  If not there’s plenty of room to anchor. 

Alternative Harbors: Castine offers dining options (but mooring or dockage is recommended) whereas Smith Cove is well, scenic and spacious.  

Day 6:  Pulpit Harbor

Distance: 14 nm

After a likely beat down the bay in a sparkling sea breeze, Pulpit is always worth a second night’s stay setting up a short hop back on your last day.

Alternate Harbors: include Cradle Cove and Warren Island

Day 7:  Back to Camden, Rockport, or Rockland

Distance: 8 to 10 nm