Sailing the Maine Coast Rockland to Mount Desert Island

Sailing the Maine coast is by far the best way to see it! Better than driving, which we call the Route 1 Blues. And we’d add – the true Maine coast starts Midcoast, think Boothbay Harbor and beyond, for spectacular scenery. Shimmering rocky coast contrasts towering evergreen forests, framed by a mesmerizing blue sea. Along the interesting Maine shoreline are frequent Maine lighthouses plus the ever-present lobster boats zipping around bays, a plethora of birds and harbor seals, and a few other pleasure craft. Otherwise it’s serenity.

Captain Greg and I sailed out of the bustling port of Rockland, named for its burgeoning rock trade back in the day – the source of limestone and granite that built much of NYC and DC’s monuments. For our week, we had our sights on cruising the Maine coast, exploring passageways and thoroughfares from Penobscot Bay all the way to MDI – Mount Desert Island, home to Acadia National Park.

We boarded our 1990 Sabre (made in Maine) sailboat charter “Lucky Dog” in Rockland during Maine Lobster Fest. We luckily zipped through town just after the parade ended. After our 90-minute orientation of our charter vessel, everything from how the galley functions, to seacocks, installing the dingy engine, to sailing procedures and anchoring instructions. Soon we were cruising out of Rockland Harbor past the beautiful Rockland Breakwater Lighthouse. We were in good company with the US Coast Guard Cutter Eagle and a Tallship in Harbor for the Festival. The skies had cleared after a significant rain and thunderstorm, and the Bay was surprisingly calm – not enough wind so we motor-sailed. Already “Lucky Dog” seemed apropos as we learned our way around her decks and Greg navigated her with his pre-plotted itinerary.

Our 1^st port was North Haven as we cruised across beautiful Penobscot Bay, escorted on occasion by porpoise. The scene of granite shore rising up to the mountains of Camden was magnificent. Passing the granite monument marking Fiddlers Ledge, then Browns Headlight was a welcome sight, entering Fox Island Thorofare. We avoided ferries and numerous bright-colored lobster pots bobbing in sea swells, along with Lobstermen out checking these traps. Arriving in North Haven’s mooring field, we found a wand and mooring ball, and we were on the hook for our first night!

After getting settled onboard, we launched “Lucky Pup” the dingy, and tied up at the dock for a walk through the time-elapsed town of North Haven, which consists of a brew pub, the Landing lunch spot, and the charming Nebo Lodge up the hill where we dined on delicious lobster served in homemade pasta. The owner Angie introduced herself, it’s that kind of cozy, yet surprisingly sophisticated for a small island.

Back aboard our sailboat, a spectacular sunset over Penobscot was shrouded with mysterious fog. Our night’s sleep aboard “Lucky Dog” in the VBerth was peaceful, save for a fiddler playing on a distant schooner, and the occasional sway from a wave of a passing vessel.

Day 2 we awoke with the early Maine sun. After a fortifying percolator coffee, we headed for Deer Isle Thorofare en route to Little Cranberry Isle. We motored through light fog, a Sunday morning so the waters were eerily quiet, no lobstering allowed today. Captain Greg’s radar indicated rain and thunder, so we grabbed a vacant mooring in Stonington to wait it out. With partially improved weather, we plied the calm foggy waters, with too many seals to count popping up for a breath and then disappearing into the dark waters.

Boating in fog is challenging to your senses, eerie and disorienting at times, when you can’t find a navigational red nun or green can, then it pops up suddenly in front of you through the haze. Even more surprising is another vessel! Navigating fog is rewarding too, when you reach that elusive mark on your chart, and incredibly satisfying to make your planned destination – obviously!

A glimpse of grand Mount Desert Island appeared ahead; the rocky Cadillac Mountain was shrouded with a cloud skirt – a magnificent sight that then magically disappeared as we rounded Bass Harbor Light toward our mooring for the night at Little Cranberry Island. Our evening dinner at Isleford Dock Restaurant in a corner table facing the humble happy harbor of lobster boats and visiting sailboats, we had THE best Lobster Thermidor ever! Good news: this is the only dining spot on LCI – it is also the best. Next morning we walked around Lil Cranberry – a rustic island, which locals say is host to more mosquitos now than cranberries.

Day 3 we finally had wind, and sun! We raised sails and released our mooring ball (a choreographed technique Captain Greg and crew (ok, me) have mastered – not for the novice. We also finally had spectacular views of Mount Desert’s sparkly granite peaks, rolling green hills and bubbles (yes that’s what the hills are called). Lucky Dog sailed true, with gusts up to 20 mph. We tacked up toward Frenchmen’s Bay, then sailed back toward Northeast Harbor. I loved the amazing shoreline views of Otter Cliffs, admiring the grand “cottages” of Seal Harbor, waving to Martha Stewart and fellow billionaires’ mansions.

Lots of lobster pots and ferries, and wealthy summer yachters were our boating companions. We sailed into Northeast Harbor and radioed for our town dock’s slip, full of more mega-yachts. A refreshing marina shower and walk up the hill to “town” was a perfect afternoon. Lunch at Colonel’s provided a classic Maine meal – lobster grilled cheese and chowder. We browsed clothing shops, art galleries, and the Maritime Museum which was worth the $5 suggested donation to learn of the evolution of MDI from Abenakis to summer rusticators, to fishing and granite quarries. Pine Tree Market was ideal for provisions before we strolled back to our boat in the afternoon sun.

End of day 3, an extraordinary dinner back in town at Copita featured lobster arogosta for me, amazing lamb with root veggies for my captain Greg – with craft cocktails made by the proprietor/ bartender. Back on deck, we enjoyed echoes of cocktail banter aboard the 100’+ yachts. We slept well aboard cozy Lucky Dog.

Day 4 We departed Northeast Harbor, bound for Southwest, hugging Mount Desert’s shoreline, admiring the grand summer cottages of generational wealth. We poked our bow up into Somes Sound, arguably the only natural fjord in America. It is truly spectacular with granite cliffs and dense, dark green clinging pine trees, along the dramatic deep blue waterway – like Norway.

We passed kids sailing little prams in summer camp, as we rounded our boat into Southwest Harbor spying Hinkley boat facility in the distance. Everyone at Dysart Marina was super helpful. We swiftly fueled, pumped out, and filled fresh water, found our slip with dock hand assist, and checked in at reception – which was guarded by Marina, the amiable dock dog.

Strolling Southwest Harbor, there are just a few shops and galleries, but we learned the real grocery store is a mile outside downtown. So, we dined at EatAPita where the cuisine was excellent from a broad menu at this garden cafe. The Claremont Hotel, another option 20- minutes’ walk from the marina, is a classic Maine lodge completely renovated to chic elegance – so Instagramable from the oceanside pink pool umbrellas and croquet, to the cottagey spa, cozy wooden fitness cabin, and upscale waterview dining.

Day 5 after a morning walk to town for cappuccino and freshly baked breakfast sandwich at Clark Point Café, we departed the marina waving bye to crews polishing luxury yachts. We decided that the two of us sailing a 36-foot “do it yourself” was a greater adventure than being catered to on a floating five-star hotel yacht with a crew of ten. Not to mention we burned 5 gallons of fuel motor sailing from Rockland to MDI – versus the thousands of dollars we witnessed on the mega yachts’ tabs.

Glorious sunshine and 8-12 knot winds made for a perfect sail as Mount Desert’s grand granite hillsides faded to our stern. Dodging lobster pots (estimated at 3 million in the salty waters of Maine) is a full-time watch as we sailed to Black Island with its gorgeous silver shores and lofty pines, then we tacked toward Casco Bay Passage. Fish pens lined some of the remote waterways, another nod to Norway’s fish harvesting in open fresh water.

A game-day decision was made by Captain Greg with suddenly fluky winds, to sail up Eggemoggin Reach to Bucks Harbor, versus back through more exposed Merchants Row. How fitting, we held a beautiful 10-mile reach (sail-position) up this spectacular Reach in the company of several sailboats (but we won by trimming our sails says Captain). Gliding under the graceful suspension bridge brought us to Thrumb Cap Ledge, Pumpkin Light, and the entrance to idyllic Bucks Harbor – the summer home of Robert McCluskey, author of “Make way for ducklings” and “Blueberries for Sal”, along with “One morning in Maine.” Bucks Harbor Marine and the BH Yacht Club line the horseshoe bay waterfront. After a pleasant check-in at the marina HQ, we hiked up the hill to town – which consists of a small market and Bucks Restaurant – that’s it, that’s all folks. We’d provisioned our ice box with frozen dinners, now thawing on day 5, so delicious chili on board amid fellow yachters was our evening, topped with a gorgeous sunset on the bay melting into the verdant pine tree tops.

Day 6 we awoke to glorious sunshine, but our boat neighbor on his old cabin cruiser fired up his engines to charge – disrupting the tranquility of our coffee on deck. So we dropped the hook and headed out to calm, crystal-clear waters. Penobscot Bay was flat as a pond with stellar visibility, so we couldn’t lament our lack of wind as we motor-sailed by remote islands, which have been explored and settled for centuries by natives, and rusticators – well-to-do adventuring city folk. We scored a perfect anchorage amid Barred Islands’ Butter, Bartender and Escargot, in the shadows of Great Spruce Head. Our scenic picnic lunch was appropriately buttery Maine lobster bisque from the depths of our ice box. The wind picked up for our tack back across the Bay, getting busier with ferries and pleasure craft as we neared Camden and Rockland.

Our best marina greeting yet was Safe Harbor Rockland where a crew of four awaited Lucky Dog on the docks. This turned out to be our best marina facility too. Private modern restrooms awaited, with Wifi, laundry, coffee. My hot shower felt wonderful but wobbly after boating for a week. Can you say “Sea Legs?” A delicious Italian dinner at Rustica hit the spot in the charming seaport town of Rockland. Back on the dock, we watched the sunset by the fire table at Safe Harbor overlooking the bay… absolutely stellar!

Day 7 – our last day on board, started with pouring rain, like buckets on our boat, but we’d beaten Hurricane Debbie to Port and were happy to be on a face dock at such a sophisticated marina, so we could explore Rockland. What’s the saying, “I’d rather have a drink on the rocks on a dock, than be out at sea near the rocks with my drink back at the dock?!” Something like that. We spent much of our day dodging around Rockland, fueled by an amazing brunch at old Rockland Café – the best fish cakes for $4.99, and seafood stew loaded with local seafood, not potatoes & onions says the menu. Rockland’s brick-sidewalk Main Street offers art galleries galore and museums. A must-visit is Blue Ravine Gallery, don’t miss the rooftop garden and the cellar safe! More famous is The Farnsworth Museum – home to famous Wyeth family Maine artwork.

Borrowing Safe Harbor’s courtesy car, we road-tripped out to Samoset t – a lively seaside resort – to walk the mile-long breakwater of massive local stones to the Rockland Harbor Breakwater Light dating to 1827.

Everyone said go to Primo, so we did that evening to celebrate our successful Maine sail. Just a minute drive from town, this farm-to-table gem is celebrating 25 years with Chef-Owner Mellissa Kelly – James Beard recipient. Our meal and the setting were extraordinary. A fresh creative daily menu is served by an impeccable team – expectations met!

Last night aboard Lucky Dog was a bit wet and wild, as Storm Debbie blew through. Departing our new charter boat the next morning, the sun came out – a promise for another Maine coast sail next season. Sailing can be tricky, fluky, even rustic and “glampy” (rhymes with campy). But there is nothing that compares to seeing the incredible Maine coast from the sea, finding fabulous quiet harbors and ports, and being powered solely by the wind on a boat escorted by lobstermen and harbor seals.

Visit Maine for boat charters, outdoor adventure, beautiful resorts and the relaxed lifestyle of Vacationland.

More Luxury Vacation Guide Maine reviews:
Kennebunkport Maine
Boothbay Harbor Maine
Rockland Maine
Rockport’s Samoset Resort.
Camden Maine
Port Clyde Maine
Belfast Searsport Maine