Casco Bay Cruising Itinerary

Cruising Maine’s Islands of Casco Bay

New England

"If once you've slept on an island -- you'll never be quite the same."

So goes the idyllic poem by Rachel Field.

Nowhere is that truer than on a coastal island in Maine in summertime.

Casco Bay in Portland is dotted with more than 200 beautiful islands, some more inhabited than others, particularly Peaks and Long Island. The most populated are easily reached by Casco Bay Lines' ferries. We discovered three lesser-traveled islands, truly unique from one another and well worth visiting by boat.

Starting Point:

Kennebunkport, ME

Casco Bay Schooner | Marinalife
Casco Bay Schooner

Departing from our home port of Kennebunkport, my husband Greg and I cruised an hour, 20-nautical miles, in our 21' Key West to Casco Bay. Our two-day, island-hopping getaway was underway as we sped past Wood Island Light at Biddeford Pool, passed Two Lights State Park and rounded Cape Elizabeth to the iconic Portland Head Lighthouse's welcome with Ram Island Ledge Light Station to our starboard. As we entered the broad island-infused Casco Bay, lobster and fishing boats, ferries, and pleasure yachts plied in and out of bustling Portland Harbor. But we were bound north to the Diamond Islands, passing the imposing 1864 Fort Gorges granite garrison.

Leg 1: Portland to Great Diamond Island

Estimated Mileage: 3.9 NM

Great Diamond Island is a gem in the heart of Casco Bay, almost four miles outside Portland. This historic island has remnants of Fort McKinley, a coastal defense built in the 1890s to protect Portland's harbor. Arriving by boat, Diamond Cove has a pleasant, well-protected marina next to the Casco Bay Ferry dock, affectionately called Cocktail Cove by locals. Portland boaters come here to hang out for drinks and a bite at the restaurant. Having checked in at Diamond's Edge Restaurant, we were valeted by golf-cart up to the Inn at Diamond Cove. Carts and bikes are the preferred transportation around the island, which is mostly private for the 200 residents and hotel guests.

The Inn at Diamond Cove is in the beautifully renovated old brick army barracks of Fort McKinley atop the hill amid a campus of private homes. After checking into our modern, spacious room with views of the manicured parade grounds (but not the ocean from this high forested point), we biked to the beach and strolled to the old artillery spots that display remnants from the Spanish American War through World War II. After exploring, we opted to relax by the hotel's pool and hot tub in lieu of playing croquet, tennis, indoor bowling or basketball. We ordered tasty snacks and a cocktail from the Cabana Bar. Our peaceful balcony was a delightful spot to read before walking down to the waterfront for a wonderful seafood dinner at Diamond's Edge and nightcaps back at the hotel by the fire pit. Crown Jewel is another cool dining spot on the island. Decorated in cheery pink, it looks plucked from Bermuda.

Leg 2: Great Diamond Island to Eagle Island

Estimated Mileage: 6.43 NM

The next morning, we cast off for Eagle Island and cruised through picturesque miles threading between Long and Cliff Islands. Eagle Island is a dramatic outcropping on the northeastern edge of Casco Bay. The spectacular Maine State Park in Harpswell is for true explorers. Now a National Historic Landmark, Eagle Island was the home of Admiral Robert E. Perry, best known for claiming to be the first person to reach the North Pole in 1909. Grab a mooring by the western pier and dinghy in to tour his family's 1904 summer home, complete with artifacts from his bold expedition and even a polar bear! Admission is $6 for a self-guided house tour. Overnights are not permitted, so take in the ocean panorama from this prominent point before venturing along.

Leg 3: Eagle Island to Harpswell Neck

Estimated Mileage: 1.91 NM

Dolphin Cove Marina | Casco Bay| Marinalife
Dolphin Cove Marina

From Eagle Island, we took a short passage northeast past Upper Flag Island to Potts Harbor and Dolphin Marina on the southern tip of Harpswell Neck. Dolphin provides a dock slip at its expansive marina for restaurant guests. Lunch at Dolphin is special, with a commanding view down Casco Bay from the glass-lined, modern dining room and bar. The super-friendly Saxton family serves delicious, homemade and fresh seafood, as they have for more than 50 years. Don't miss the buttery blueberry muffins served with most entrées.

Leg 4: Harpswell Neck to Chebeague Island

Estimated Mileage: 4 NM

We headed west across Broad Sound to the northwest bight of Chebeague Island. If you pick up a mooring marked Chebeague Inn, the launch will retrieve you. Prepare to step back in time. Chebeague Island is Maine's newest town that became independent from Cumberland in 2007, but it's still bucolic and dates back to the 1700s. The beautiful wooded island offers several sand beaches and is home to a hearty year-round community of 350 islanders. Chebeague (pronounced sha-beeg) is the largest of the Calendar Islands, a reference to the number of islands equaling the days in the year in this region (slight hyperbole but a fun anecdote). Chebeague is actually a 17-island archipelago, and the Big Island is three miles long by one mile wide. The lovely 1880s-era Chebeague Island Inn is the crown atop a sweeping lawn that is perfect for a yachter's overnight with a view of their boat.

Beach near Sebasco | Casco Bay| Marinalife
Beach near Sebasco

From the dock, we were whisked up the hill in the courtesy van to the historic yellow hotel. A cozy stone fireplace in the living room led to a gracious veranda with sea views. After checking in to our second floor, timelessly elegant, waterfront guest room, we borrowed bikes and followed the rustic road to East Shore Beach. Two roads on the island, North and South, take you around to the historical society, the Slow Bell Cafeé, and past modest homes. The tight community of locals love to share their island history. Settlers in the 1740s farmed here, and lobsters were so abundant that they fertilized their gardens with this seafood delicacy. By the 1900s, Great Chebeague had five grand hotels, but now just one remains, accompanied by a grocery store, community center and school.

Back at Chebeague Island Inn, we sipped cocktails on the elegant old porch before a delightful dinner of local Bang Island mussels and Maine lobster in the classic wood-lined dining room. Sleeping at the Inn is serene, with ocean view windows open and white drapes fluttering in the sea breeze (no AC). In the morning, fresh brewed coffee on the veranda was heavenly before our boat trip back home.

If you love boating and sleeping on islands surrounded by the sea, then continue your Maine coastal tour onward Down East toward Boothbay Harbor. Stay at Ocean Point Inn & Resort, another historic inn with moorings, reasonable oceanfront lodging and a classic Maine restaurant. Penobscot Bay is loaded with beautiful islands and picturesque harbors in Camden, Rockport, Lincolnville and Rockland. Finally, Mount Desert Island, home to Acadia National Park and Bar Harbor, has two of our favorite harbors: Northeast and Southwest. After a Maine island excursion, you will never be quite the same.

Related Articles
No items found.

Want to Stay In the Loop?

Stay up to date with the latest articles, news and all things boating with a FREE subscription to Marinalife Magazine!

Thanks for subscribing!
Oops! Something went wrong while submitting the form.
Marinalife articles