Sailing Maine Rockland to Acadia

Sailing the Maine coast is by far the best way to see it! You can see so much more of the coast than you possibly could driving. If you think you will get off the Turnpike and drive Route 1 to see the Maine Coast you will be sorely disapointed. For us, the “real” Maine coast starts in the Midcoast Region, 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. Serenity at its finest.

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’s sail, we had our sights on cruising “Downeast”, exploring passageways and thoroughfares from Penobscot Bay, thru the famed Merchants Row up to Mount Desert Island (MDI for those in the know), 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 hometown parade ended. Our 90-minute orientation of our charter vessel covered 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 to raise our sails 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 across the bay toward the island of North Haven, escorted on occasion by porpoise popping their slick heads up.

The scene of granite shores rising up to the mountains of Camden was magnificent. Passing the granite monument marking Fiddlers Ledge, then Browns Headlight, was a welcome sight, entering the famed 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, I secured the pennant, 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 timeless 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 on Chef’s 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 Bay was shrouded with mysterious fog. Our night’s sleep aboard “Lucky Dog” in the VBerth was peaceful, save for a fiddler playing on a charter schooner across the harbor, and the occasional sway from a wave of a passing vessel.

Day 2 we awoke with the early Maine sun. After figuring out the old-fashioned coffee percolator, which made surprisingly delicious coffee, we headed for Deer Isle Thorofare en route to Little Cranberry Isle. We motored through light fog on this eerily quiet Sunday, no lobstering allowed today. Captain Greg’s radar indicated rain and thunder was imminent, so we grabbed a vacant mooring in Stonington for an on-board picnic lunch 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, downright disorienting at times, when you can’t find a navigational red nun or green can, then it appears 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 few hours of motor sailing and 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 the resplendent Isleford Dock Restaurant at a corner table facing the humble happy harbor of lobster boats and visiting sailboats, we had THE best Lobster Thermidor ever! This is THE dining spot on the island. 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 quick 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 exciting gusts up to 20 mph. We tacked up toward Frenchmen’s Bay, then sailed back to 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’ summer 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, to today. 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 dock-mates; banter aboard the 100’+ yachts. We slept well aboard cozy Lucky Dog.

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

We passed kids sailing little prams in “summer camp”, as we rounded our boat into Southwest Harbor spying The Hinkley Yacht 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 the amiable marina dock dog, named aptly “Marina”.

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 lush croquet courts, 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 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) was 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.

A game-day decision was made by Captain Greg. Instead of tacking into the wind through Merchants Row, the breeze was better for a 22 mile reach up through beautiful Eggemoggin Reach to Bucks Harbor. We were accompanied by several sailboats (but we won by trimming our sails says Captain) during this spectacular reach. 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 quiet 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 yummy homemade stew on board amid fellow yachters was our evening, topped with a gorgeous sunset on the bay melting into the verdant pine treetops. Of note, Buck Harbor Marina had been closed least a season, but with new owners and new mooring balls for 2024, they are back in business!

Day 6 we awoke to glorious sunshine, but our boat neighbor on his old cabin cruiser fired up his engines to charge his batteries – 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 greater depths of our ice box. Afternoon winds 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 back 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, fortified 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 Resort – 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 – a James Beard recipient. Our meal and the setting were extraordinary. A fresh creative daily menu is served by an impeccable team – expectations were high and they were met and exceeded!

Last night aboard Lucky Dog was a bit wet and wild, as Storm Debbie blew through. Lucky Dog was a bit of a leaky dog, jokes on us! 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:
Boothbay Harbor Maine
Rockland Maine
Rockport’s Samoset Resort.
Camden Maine
Port Clyde Maine
Belfast Searsport Maine