A Penobscot Cruise Plan

No, it is not heaven, merely the view of Buck’s Harbor area from Caterpillar Hill

This Maine Charter Cruise Plan is quite wide-ranging and somewhat ambitious….particularly because it includes a trip Eastward to Mt. Desert, Island and Somes Sound (a popular destination). A day of inclement weather or foul winds can make the plan a bit too ambitious…but the cruise guide is provided to raise some possibilities. Because you begin so centrally located at the heart of the Penobscot Bay you can mix and match these locations quite freely without long passages. Our office can also give you alternatives and specific locations for your interests such as antiquing, craft, history, boatbuilding, music, etc. All of these cruise options have been personally visited and experienced by us as quality destinations.


A.M. Provisioning, Stowage, Cruise & Boat Briefings
1200-1300 Departure.

Sail between Buck’s Harbor and Beach Island to familiarize yourself with boat.
Come about and head down the Eggemoggin Reach under sail to anchor at WOODENBOAT Magazine Estate (lagoon behind Torrey Island)WOODENBOAT Magazine is produced on a large old Maine estate restored & given over completely to wooden boats. You can visit classes at the Woodenboat School, picnic on their waterfront, and visit their unique store. They also have one of the finest Marine Libraries on the East Coast. A protected harbor. Guest moorings available from Woodenboat waterfront office via VHF. The entrance is easy and holding ground good.


Head down the Reach past Naskeag Point bound for Mt. Desert Island via the Casco Passage.

Sail to Mt. Desert Island. Overnight in Northeast or Southwest Harbors.

If you have chartered a sailboat, the decision to go to Mt. Desert Island involves a commitment of two days and will affect your time in other parts of Penobscot Bay.
While the Island and Acadia National Park are nationally well known and have many things of unique beauty and interest it does mean running Easterly and back. If you have chartered a power boat with a fair turn of speed, then you could venture East and return quickly to the central Penobscot.

A note about Mt. Desert Island and Acadia Park. Many people have heard about Bar Harbor, Southwest Harbor and Northeast Harbors as well as Acadia National Park. The cruising sailor should realize that these are very popular destinations — and you will encounter many, many people and tourists there. In recent years, large cruise ships on the order of the QE-2 and other major cruise vessels make regular stops in these harbors (in addition to Maine Windjammers). This sudden and large influx of several hundred (or thousand) people, and the accompanying commercialism of towns like Bar Harbor has essentially changed the nature of these places. The restaurants are great and Acadia National Park is certainly wonderful ( and there is some public transport that will take you to the Park from these Harbors) — but, again, the solitude and unique beauty of the Maine Coast can be found elsewhere. Be warned. There are also portions of Acadia National Park located on the island of Isle Au Haut which is more central to the Penobscot area.

Looking Northwest towards Stonington from Merchant’s Row


Sail to and through Somes Sound, Mt. Desert Island.

Rent Mooring in Southwest Harbor and tour Hinckley facility. If you want to do this we should call to arrange it if possible. Or arrange for a carriage or bus tour of Acadia Park.

Dinner in Southwest Harbor. (Note: the mooring area to port at the entrance of and at the base of the cliffs of the Somes Sound fjord fills up very early in the day. Also, Somes Sound is beyond reasonable dinghy range of Southwest Harbor. Better to just motor up and down the fjord and then go to Southwest Harbor for a mooring (rented from Hinckley, or stay at a slip in the full service Great Harbor Marina. The head of the Sound is quite beautiful and sometimes moorings are available there. Beware approaching Great Harbor Marina in bad light or fog….there is a rather substantial rock right in front of the approach that is hard to see.


Mt. Desert Island to Swan’s Island, Burnt Cove Harbor.

Note: This would be Day Two if you opted out of traveling to Mt. Desert Island.

A good sail with good wind through Jericho Bay. Only attempt the harbor entrance in good daylight. (We will show you how). We believe that the Coast Guard has removed the exterior harbor buoy shown on your charts. When you pass the lighthouse at the harbor entrance you are in a totally protected harbor. Swan’s Island feels remote, and has the true flavor of the Penobscot. This island makes its living fishing for lobster and is virtually untouched by tourism. There is a totally protected harbor and rental moorings. You can sleep well and secure here. Good lobster available and a nice place to explore the town on foot or with dinghy. A lovely Maine place.

McGlathery Island looking toward Isle Au Haut

NOTE: If you opt not to include the days at Mt. Desert Island to the Eastward, you can go directly to Swan’s Island from your first night at the WOODENBOAT anchorage…..and, accordingly, you can add time at the following places — or add stops at Brimstone Island, Stonington, Harbor Island, Isle Au Haut, Pulpit Harbor, the Barred Islands, the White Islands south of Vinalhaven, or (if you need at least one night in a large town) a stop in Camden or Castine.


 Swan’s Island to McGlathery’s Island (in Merchant’s Row )

Note: This would be Day Three f you opted out of traveling to Mt. Desert Island.

This is a completely uninhabited small wild Maine Island which my wife and I consider to be one of the most beautiful in the State. Great anchorages, quiet hidden paths, terrific climbing on pink granite, wonderful old growth forest and open wild flower field, even a good beach. A careful entrance needed (again, we will show you how to do this). An early afternoon arrival is important to beat any other boat to the best anchorage in the small cove. This is an uninhabited, protected Island that permits public access. Here you will find the peace and quiet that is the natural sailor’s World – which is, why you came to Maine. If approaching or departing to the Southwest check with our office to point out a significant rock hazard at the harbor entrance.


 Stonington, and on to either Isle Au Haut, Brimstone Island, or Vinalhaven

Note: This would be Day Four if you opted out of traveling to Mt. Desert Island.

If you can tear yourself away from McGlathery’s…..go in to Stonington, Me. at the southern tip of Deer Isle and get breakfast or lunch. Good food and pies at Harbor Café. Homemade ice cream on Main Street. This is a fine Maine fishing village (about 300 lobster boats) which has a great shipyard (Billings) and is a very nice town to walk through. Many homes of fishermen built on pilings, lobster pounds, a granite museum (the stone for Radio City Music Hall, the Empire State Building and John Kennedy’s grave came from Stonington’s Crotch Island quarry). French Victorian homes, etc. Some good café lunch spots. A very walkable village. You can rent a slip or ask for some dock time at Billings Diesel & Marine (or we can arrange it for you). After a good breakfast or lunch in town, motor on to either Isle Au Haut (weather permitting), sail to Brimstone Island to see its spectacular black stone beach, or go on to Vinalhaven or Seal Bay and its surrounding Islands. Or, if you want take another day in McGlathery’s or nearby.

Isle Au Haut is part of Acadia National Park area and has wonderful old growth forests, wild berry fields, and some imposing granite cliffs to the South.


 Passage to Upper Penobscot Bay.

A good day’s run up the Bay.

Some choices…..depending on your prior choices and whether you went to Mt. Desert island or not.

The White Islands

These are an isolated group of beautiful Islands just to the west of Vinalhaven Island. They contain a totally protected harbor, tidal pools, a small beach and wonderful granite formations. Very few boats go there. We can provide you with the necessary local knowledge to get into this terrific hideaway. From the White Islands, it is an easy run to the following destinations.

Camden, Maine

Quite a builtup town, with a major boatyard (Wayfarers), many nice shops, some good restaurants. Quite busy, but walkable. You can dock at Wayfarer.

North Haven

A nice town right in the middle of the Fox Island Thorofare. Quite old (early 18th Century) town with some French influence. Good restaurants, nice walks both in and near town.)

Pulpit Harbor

A lovely quiet harbor on the Western side of North Havaen where you can get a very nice mooring. A favorite sailor’s spot.

A stroll on Maine’s granite ledges on Isle Au Haut

Castine, Maine

A good day’s run. This is a fine historical town dating back to Colonial era. A famous battle of the War of 1812 was fought here. The home of Maine Maritime Academy. A good restaurant here and available rental moorings.

Some lovely homes and a good walkable town.

…..and, a short hop back to Buck’s Harbor the next morning which can be done
in virtually any weather.

Alternatives for this night would also be to stop short of Castine and anchor in the Barred Islands (very remote hidden anchorage), or off Pond Island (a wide beach and quiet anchorage in all except Southern wind—-

OR……spend your final night in Buck’s Harbor, pick up the boat’s own mooring, take one of our great outdoor (or indoor) showers, cook up some lobsters for dinner, and watch the sun go down past Cape Rosier.

After all, we are most other folk’s real destination.

Home Base at Buck’s Harbor Marina


Places & Sights


  • American Bald Eagles
  • Osprey
  • Heron
  • Egrets
  • Cormorants (Shags)
  • Loons
  • Seals
  • Dolphin
  • Small Whales at certain times
  • Runs of Mackerel and herring
  • Wild Duck
  • Heron
  • Striped Bass
  • Eagle Island Light (Eagle Island)
  • Pumpkin Point Light (near Buck’s Harbor)
  • Isle Au Haut Light (on Isle Au Haut)
  • Pink Granite (Stonington and Merchant’s Row)
  • Maine Windjammer Schooners
  • The Holbrook Wildlife Sanctuary (Cape Rosier near Buck’s Harbor)
  • The Nearing Farm (Living the Good Life, etc.) (Brooksville)
  • The Wyeth Collection (3 generations) at Farnsworth Museum (Rockland)
  • Haystack Craft Center (Deer Isle)
  • Maine Maritime Academy (Castine)
  • Reversing Falls (Horseshoe Cove near Brooksville)
  • Caterpillar Hill (near Brooksville)
  • Stonington Opera House Now a Performing Arts Center (Movies & Theatre.
  • The Woodenboat Gathering & Regatta (120 Classic large wooden boats compete
  • In a series of races. The best of which is on Eggemoggin Reach
  • Into Jericho Bay. August 1-2.
  • Swan’s Island Folk Festival – week after Woodenboat Regatta
  • Maine Windjammer Gathering, Race & Gam
  • Maine Boat’s & Harbors Show (Rockland, Maine)
  • Woodenboat Show
  • Lobster Boat Races (throughout the summer at various locations)
  • Kneisel Hall classical music (Blue Hill, ME)
  • Stonington Opera House (plays, movies, musicals, special events)
  • Lobstering (If you have the time, we can arrange for you to go out with a local lobsterman to tend his traps.
  • Childrens Reading Programs and Computers (Blue Hill Library)