Cruising Stories

Cruising the Maine Coast - From Portland Harbor to Mount Desert Island

Local Knowledge is Key

New England

Our Maine boat adventure began before we even left the dock with a crash. No, not into another boat, but of our friend, tumbling down the ramp at low tide. I have to give her credit, she spilled not a single beer out of the overloaded cart into Portland Harbor, nor did she shed a single tear. Friends of ours had purchased a beautiful new 48-foot Sabre and invited us along as crew for the maiden voyage we're locals who know our native Maine waters. But our first order of business had to be getting medical attention for our stoic friend's quickly swelling shoulder. Two hours and X-rays later, we were all back on board sipping drinks, one broken humerus in a sling. Our wounded one, whom we dubbed One Wing, insisted that we stick to our itinerary and head Down East in the morning.

After a nice dockside dinner at DiMillo's Marina and a night's rest in the gracious staterooms, we awoke to squawking seagulls and a perfectly calm sea and sun. We set out on our 98-nautical-mile journey to Mount Desert Island and Southwest Harbor. It was a beautiful passage out Casco Bay by Halfway Rock and Seguin Island, with a lunch anchorage in magnificent Merchants Harbor, off Merchant Island south of Stonington and Deer Isle. Merchant Row is famous for its 40-plus islands, loaded with grand pines and sloping granite boulders that meet the brilliant blue sea. As we traveled farther Down East, the seals and porpoises became more plentiful, the pink and silver sparkling shores more splendid. This is true Maine, best seen by boat ideally, aboard a brand new 48-foot Maine-made Sabre (and even better if it belongs to friends).

Passing Bass Harbor Headlight to our port we circled past Cranberry Islands, Big and Little, and Bear Island Light, with a scenic detour into Northeast Harbor. After a harbor tour, we poked our bow into Somes Sound for a view of North America's only fjard (like a fjord). Our ultimate destination was Dysart's Great Bay Marine in picturesque Southwest Harbor where we would dock for the next two nights. In the fine company of Hinckley and Morris Yachts, made right here, we enjoyed Dysart's peaceful but well-equipped marina. Showers, WiFi, and Grumpy's restaurant for a bountiful homemade breakfast were all in sailors' reach. Jane and the Dysart's crew were super-helpful and friendly, suggesting walking paths, outings and places to dine. Our crew browsed the shops of Southwest Harbor - favorites included Moody Mermaid and Sawyer's Market. Strolling the quiet island streets toward Clark's Point, where the US Coast Guard is stationed, and Beal's Lobster Pound was a great leg stretcher. We did not take advantage of the Island Explorer, the free bus system of Acadia National Park, sponsored by LL Bean, that would have transported us to Bar Harbor. We preferred staying on the quieter side of Mount Desert Isle. Next time, we will have to hike Acadia Park (when no one has a broken arm) and play a civilized game of croquet before sunset cocktails at the 1883 Claremont Hotel, with its perfect vantage toward Somes Sound.

We were up with the sun and off the hook the next morning. After a scenic swing through Bass Harbor, a classic Maine fishing village, we cruised by the spectacular Blue Hills to our north. Entering the mile-wide Eggemoggin Reach, a boaters paradise and one of the prettiest channels anywhere, we glided along the 10-mile passage on smooth waters past The WoodenBoat School, then past idyllic Center Harbor on the mainland and Deer Isle to our port. Cruising under the huge Eggemoggin suspension bridge, which soars to 85 feet at its center, is impressive on any vessel. As we emerged from the reach around Pumpkin Island Light off Little Deer, we rounded the point of Cape Rosier, a cliffy shore with magnificent homes clinging to the hillside, to see amazing views of Camden Hills in far-off Penobscot Bay.

Our next port was Castine, the picturesque peninsula village where Maine Maritime Academy is based. This historic town is as charming as it has been challenged by occupations since the 1700s from Native Americans to the Dutch, French, and British, and now to the college kids studying oceanography and marine engineering. From Castine's Town Dock we walked to a sunny al fresco lunch at Dennett's Wharf Castine's waterfront gin joint. Clams, calamari, mussels and Maine seaweed salad never tasted so good, accompanied by a cold Maine microbrew and a view of the Bagaduce River. After lunch, we contributed to the sail loft ceiling's collection of dollar bills, a fun tradition that has benefited the families of 911, Hurricane Katrina and a local fireman.

Castine is a gem to explore, from the cute ice cream and craft shops, to the elm tree-lined streets, to the battle bunkers and forts perched by the sea. Dyce Head Light is private, but Witherle Woods is a wonderful public preserve of trails where we hiked to a bird's eye view of Penobscot Bay on Lookout Loop. Dinner in Castine at the Pentagoet Inn was extraordinary - this traditional 1894 inn serves local seafood, lovingly prepared. A gorgeous sunset on the boat concluded our perfect Castine day.Next morning, crystal clear calm waters brought us to Pond Island, a postcard-perfect uninhabited island in the heart of Penobscot Bay with a tidal pond at its center. We anchored and brought the dinghy to the beach, which was loaded with smooth skimming stones, driftwood, seashells and a few sand dollars found by none other than One Wing, her eagle-eye senses heightened.

Bucks Harbor was our next mooring. This beautiful horseshoe cove is well protected and poetic. Brooksville and nearby Brooklin inspired the literary works of E.B. White (Charlotte's Webb) and Robert McCloskey (One Morning in Maine, Blueberries for Sal, Make Way for Ducklings).

Bucks Harbor Marine provided us with a big secure mooring ball amid the clinking of sailboat masts and along the calm shores where a few cottages and the third-oldest yacht club in Maine sit. Bucks Harbor facilities include a large dinghy dock, refreshing outdoor showers, WiFi, provisions and a chance to walk on land. A short walk up a steep hill and we were on a quiet lane heading to town, which consists of a general store, church and Bucks Harbor Restaurant. What more do you need, right? Watching the sun set from the boat was a signature end to a sublime day at sea.

The next morning we cruised by the lighthouse on Pumpkin Island, heading for Stonington on the southern tip of Deer Isle, for Fourth of July festivities that promised an old-home-day parade, lobster bake and crustiest crab contest, and fireworks. But bang, something hit our hull, a log perhaps, and got the better of one boat prop  big bummer. With twin screws we weren't dead in the water, so we turned toward Belfast for repair.

To say the adventure started and ended with a bang is bad, sad form. So Stonington will remain on our boating bucket list, because there is so much more to explore by boat in this beautiful part of Maine.

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