Where do you go on a Maine Windjammer sailing cruise?
One of the unique aspects of a windjammer trip is that you don’t know where you’ll end up each evening. There’s no set itinerary, though in general the windjammers sail the Maine coastal waters between Boothbay and Bar Harbor. Each trip is different! While a seasoned windjammer guest may visit some of the same islands and coastal towns over the years, there are always more islands to explore and no two trips are ever the same.
One of my perks as the association manager for the MWA is that I occasionally get out of the office and on to a windjammer! I was lucky enough to set out on the Grace Bailey last week and I’ll tell you where we went. On our four-night trip we were treated to three and a half days of great sailing and five different anchorages – not to mention evenings full of music, lots of lobster and a touching birthday celebration.
We left Rockland on Friday morning in a beautiful steady southwest breeze. Sailing downeast toward Mt. Desert Island (home to Acadia National Park), we passed the Schooner Mary Day who was winding her way through the islands. With a brisk breeze behind us we were able to make 8-9 knots sailing through Penobscot Bay and into the Merchant Row archipelago. This archipelago is made up of dozens of islands that dot the waters of Maine’s coast and is popular for lobstering, kayaking, and sailing. Sailing through this area also takes one past Mark Island lighthouse, whose horn is one of Penobscot Bay’s most identifiable and reliable sounds.
Continuing on we headed into Blue Hill Bay and settled in Pretty Marsh harbor for the evening. Pretty Marsh is on the western coast of Mt Desert Island and borders on Acadia National Park.
Next morning, Captain Sam and crew got an early start raising the anchor and we motored over to Bass Harbor, another scenic cove off of Acadia National Park, where everyone could go for a walk ashore. Some of the guests hiked out to Bass Harbor Lighthouse, others took a short stroll along the country roads. The crew procured lobsters right from a lobster co-op – the lobsters probably didn’t come off the boat more than an hour earlier!
With lobsters in crate, we sailed over to the Deer Isle area to a small island unnamed on the chart. Now, I’ve been windjamming in various capacities for over 20 years, and I had never been to this secret spot before! This picturesque little island had a small hiking path through the trees or you could walk along the rocky shore to circumnavigate it. And it was surrounded by more beautiful islands – the view couldn’t be beat. That night, guests were invited to take a turn sailing in the little side boat.
The following morning we headed over to the town of Stonington on Deer Isle, This year-round coastal community has a large working waterfront where fishing has sustained generations of local families. Stonington also has a few small galleries, coffee shops, an ice cream stand and a miniature replica village which is fun to explore.
Leaving Stonington we had a leisurely sail over to Islesboro, one of the large islands in the middle of Penobscot Bay. Fourteen miles long with a year round population of 583 (according to the 2020 census), the island and its surrounding smaller ones offer sailors a paradise of snug anchorages. We hunkered down expecting some rains to sweep through but were pleasantly surprised that most of the storm seemed to go around us.
On Monday morning we had to head back to Rockland but Mother Nature had one more treat in store for us. Someone spotted a fin protruding from the waves and Captain Sam was able to motor us right over to it to discover this fine ocean sunfish (as known as a mola-mola).
With my belly full from that morning’s lobster quiche and happy to have seen such a unique creature so close, I begrudgingly went into my cabin to pack up. Just after we docked back in Rockland, we saw the Schooner Stephen Taber heading out for a four-night trip – I wonder where her journey will take her.
Categories: Maine Islands, Maine Windjammers, The Maine Coast
