Itinerary for Yachts International, Aug 27th – 31st, 2012
Monday 27th August, all guests arrive at DiMillo’s Marina, Portland, Maine
The itinerary below was provided by Joyce Black with excerpts from Captain Greg Russell’s expanded itinerary, which all guests received upon boarding.
For the full article by Joyce Black, click here.
Monday 27th August:

Board Lady J and after everyone gets settled in, have a light welcoming lunch before we embark on our journey! We’re off on a 36 mile, 4 hour run up to Christmas Cove, up the Damariscotta River in South Bristol.
“Ever since Christmas 1614, when Captain John Smith dropped anchor in this picturesque spot, Christmas Cove has been a favorite of sailors. The protection is excellent, and it is not far off the east-west path. Christmas Path is a busy little place, always full of movement, but it retains its wonderful, low-key atmosphere. Seals, mallards and ospreys share the cove, along with a multitude of cruisers.
Tuesday 28th August:
Before breakfast, we’ll pick up anchor and head on a short 13 mile ride over to Monhegan Island, so get up early and enjoy the beautiful morning! We’ll journey along the outer islands, so keep a keen eye out for migrating whales. After breakfast, strap on your walking shoes as the island is full of beautiful nature trails, or visit an artist’s studio as the island has more than 20!
Places that are hard to get to are often the best. Unspoiled and beautiful, 1.4 miles long and .7 miles wide, is stands majestically alone, 10 miles out to sea, with its own personality and a wonderful sense of remoteness. Monhegan remains as independent in spirit and fact as it is possible to be in the United States. As one islander put it, “What makes Monhegan different is that it is hard to get to and hard to live on, and anything that makes it easier is a step in the wrong direction”.
As you hike the trails, especially in Cathedral Woods, keep your eyes open for the unique “fairy houses” hidden within the forests. Construction of these tiny houses, built from moss, branches, rocks and other objects, has been a long standing tradition among local children AND adults. However, so as to better preserve the Monhegan forests their construction is now discouraged. Should you stumble upon one of the fairy houses, the locals ask that you treat them well by not touching them or trying to add to them.
Come back to lunch and by midafternoon we’ll pick up anchor and head for Hurricane Sound, Vinalhaven for the night. It’s a 30 mile trip, approximately 3 hours as we head up into Penobscot Bay.
Penobscot Bay is the second largest embayment on the East Coast. In all there are almost a thousand miles of shoreline including 624 islands and ledges. The largest and most populous of these is the island of Vinalhaven – only 12 miles from the mainland but another world. Penobscot Bay spreads 40 miles long and 15 miles wide, graced by more than 200 islands. Between them lie great stretches of open water and small, winding thoroughfares. Along their shores are bustling fishing communities, quaint villages, isolated outposts, and uninhabited beauty. The winds are generally moderate and predictable, and the dangers are well marked. There are winding thoroughfares to thread, endless gunk holes to explore, and a hundred harbors tucked away. Arguably Maine’s best cruising grounds are Penobscot, Blue Hill, and Frenchman bays.
The islands of Penobscot Bay are as interesting as its shores. At the western entrance lies the archipelago of Muscle Ridge, once important for its granite quarries, now sparsely settled by fishermen. Among these islands and ledges are two or three anchorages that have hardly changed since Indian times.
In the late 1870s, Hurricane Island was a thriving community with a post office, bank, pool hall, bowling green, bandstand, ice pond, ball field, boarding houses, and dozens of cottages. Quarrying was big business at the time and Hurricane was known for having the finest polished granite. The fine-grained, gray-white granite from the islands was shipped down the coast and used to build the grandest buildings of the time: the Metropolitan Museum of Art, the Cathedral Church of Saint John the Divine, the Lincoln Memorial, and many others. Around the turn of the century, concrete replaced granite. The quarries closed by 1915.
Wednesday 29th August:

Another early start as today is our Lobster Bake on Butter Island! We begin steaming up through Penobscot Bay as we make our way through the bustling Fox Island Thorofare and take in the impressive display of scattered summer manors along the islands shore.
The Fox Island Thoroughfare is a one-of-a-kind natural east-west passage between Vinalhaven and North Haven Islands, known historically as the Fox Islands. The western entrance to the Thorofare is just south of Pulpit Harbor, a destination in its own right. The Thorofare has the beauty of coastal Maine, stunning scenery, history, a working harbor, and with a myriad of coves, back waters, and anchorages, it’s a cruising destination in its own right.
It’s a 2-1/2 hour journey up to Butter Island, as we want to take advantage of the low tide, so we will do our bake around 2pm on the beach.
Butter Island, west of Deer Isle and north of Eagle Island, has long been a popular destination for cruising yachtsmen and local residents. There are lovely beaches to explore, abundant berries, and a 186-foot peak to climb. Like so many islands in Mine, Butter was settled by fishermen and farmers, beginning in 1785. In 1895, however the island caught the attention of George and Emory Harriman of Boston, who envisioned an “Arabic-like town of tents and cottages” for genteel Bostonians of good social standing.
Butter was renamed Dirigo, after Maine’s state motto, and a hotel was built to accommodate as many as 100 guests. The New England Tent Club provided comfortable quarters and vigorous activities for their enthusiastic guests, who arrived by steamer from Boston. The round trip costs $5.50 leaving Boston at 5pm and arriving at Dirigo at 7am, after a change in Rockland.
After we have stuffed ourselves with lobster, clams & mussels, we head up to Holbrook Island Harbor, which is near Castine for the night. This is a short 1 hour ride and so much to see and do here!
Holbrook and Nautilus Island form a beautiful harbor cradled in the northern tip of Cape Rosier just south of Castine. Not only is there good protection, but you will be treated to glimpses of the Camden Hills, Islesboro, Castine, and Dice Head Light. Although it offers less protection than neighboring harbors to the east, Weir Cove, on the southeast side of Cape Rosier, is a lovely anchorage in settled summer weather and a good harbor if the wind is from the north.
Horseshoe Cove is a slot on the eastern side of Cape Rosier, not far from the entrance to Eggemoggin Reach. On the chart, it looks impossible to enter. But once inside, this beautiful, unspoiled harbor has almost perfect protection. Large, granite-block moorings are set out by Seal Cove Boatyard. Hang on a vacant mooring and check with the yard.
Orcutt Harbor, on the east side of Cape Rosier, is just west of Bucks Harbor. The harbor is attractive, easy to enter, and well-protected except from the southwest. In a northerly it would be a wonderful refuge. Orcutt is little used by yachtsmen, who perhaps prefer the amenities and security of Buck Harbor next door.
Holbrook Island Sanctuary has a beautiful launch or landing site along with sand beaches, undeveloped shores, and a 120-acre island. The Sanctuary has two heavy guest moorings off the southeast flank of Holbrook Island, at the northern edge of the cable area shown on the chart. Use the southern entrance and beware of the rock farther to the north. The mile-long island is bordered by rocky ledges, sandy beaches, and mud flats. But with its approximately 115 acres of woods and fields, you wouldn’t know the island has a long human history. Settled just after the Revolutionary War by Captain Jesse Holbrook, the island’s tall pine forest provided the wood for sailing ships built in nearby Castine. The last owner of the island, Anita Harris, willed it to the state of Maine on condition that it be maintained “as a wildlife and natural area…devoted wholly to the preservation of nature.”
The many different and protected ecosystems of Holbrook Island Sanctuary are there for visitors to enjoy. So load up the kayak, find the launch, and set out to explore the scenic natural beauty of the area. After a leisurely time of sea kayaking, you’ll sleep soundly that night.
Smith Cove is a place for quiet paddling and birding, while the Bagaduce River has very fast currents challenging to even the most experienced paddlers. Ram Island, open to the public, is managed by the Conservation Trust of Brooksville, Castine, and Penobscot. On the north shore of Cape Rosier, due south of Ram Island, is a spot known locally as Tom Cod Cove, a lively and well-protected anchorage.
Thursday 30th August:
2 proposals for today, as we’ll need to be in Camden late afternoon on the dock.
Option One: After breakfast, get the jet skis and kayaks in the water and explore the sanctuary and brave the cool water and explore the Bagaduce River by jet ski. Or take a cruise up into Castine and explore the myriad of antique and artist shops. Or enjoy lunch here before making the 2-1/2 journey into Camden.
The current in the Bagaduce River is particularly fast at the Narrows at Jones Point, a few miles northeast of Castine. The Coast Pilot recommends passage only at slack water. The logical way to paddle the Bagaduce is with the current, starting up through the Narrows on a rising tide and returning after the tide begins to ebb. The Bagaduce River empties out past Castine, and the current is swift.
Upriver, the abatements of the ME 176 bridge, squeeze the Bagaduce, creating a reversing falls. Whitewater kayakers and canoeists sometimes practice in this narrow rapid, so sea kayakers may want to turn around below the bridge. The bridge is a dividing line for tidal current. When the tide is dropping, water is still pouring south under the bridge. Because there is no public portage around the bridge, if you decide to run under it, you may be stuck there for a while.
The Bagaduce River is a neutral embayment, meaning that it is an extension of Penobscot Bay rather than a river with a major source of fresh water. There are unusually large areas of mudflats and marsh.
OR
Option Two: The same, after breakfast take a 2 hour trip down the cost and proceed into Pulpit Harbor for the day before making the 1 hour journey into Camden.
PULPIT is a true harbor, nearly landlocked, on the northwest coast of North Haven Island. It is easy to get to, easy to enter, and stunningly beautiful. As you approach, a hidden entrance reveals itself, guarded by an osprey nest on Pulpit Rock. Once inside, the protection is excellent for a hundred boats or more. In the evening, the sun sets through the harbor entrance and over the Camden Hills. And Pulpit is only a two-hour sail from Camden or less than an hour from the Fox Islands
Pulpit’s beauty, accessibility, protection, and its size make this ground zero for Penobscot Bay cruising. It’s on the harbor list of nearly every boat that is cruising the bay for the first time, and yacht club cruises rarely pass it by. But if you want one of the best sunsets on the coast of Maine in a setting you will never forget, here’s a contender.
Friday 31st August:

Wake up to a great morning, maybe a short stroll into town before everyone makes the journey’s home.
CAMDEN is one of the jewels of Penobscot Bay. This beautiful harbor is home to a large fleet of picturesque windjammers and cruising boats of every kind. Curtis Island, with its lighthouse, guards the entrance. The steeples of the small town are white against the hills. A stream cascades down into the head of the harbor. There are excellent marine facilities, good restaurants and stores, entertainment, mountains, and lakes. All of these attractions have not escaped notice. The town was deluged during the 1992 filming of The Man Without a Face, starring Mel Gibson, and it is always busy during July and August. Still, Camden remains a pleasure for the cruising family. The inner harbor is extremely well protected but also crowded. You are likely to end up on a mooring in the outer harbor. Exposure there is to the south and southeast, and some nights are rolly. Shipbuilding was a major industry in Camden well before the Civil War. Holly M. Bean is the best known of the Camden builders. The Bean yard stood where Wayfarer Marine is today, and they built the world’s largest five-masted schooner and the first six-master in 1900. Among Camden’s many noted citizens, Captain Hanson Crokett Gregory claims an unusual spot in history. In 1847, with a sudden stroke of genius, he poked a hole in his biscuit to place it over one of the spokes of his ship’s wheel while he navigated, thereby inventing the donut hole. Lest Captain Gregory’s contribution to the good of mankind slip into historical obscurity, proud citizens of Camden have recently revived a long-lost tradition of celebrating the Hole in the Donut Festival in June.