Next Stop: Island-Hopping the Maine Coast
Maine’s rugged coastline is a masterpiece—home to hundreds of islands and harbors, each offering its own blend of natural beauty, rich history, and unspoiled charm. A Windjammer cruise is your gateway to the hidden gems of Penobscot Bay and beyond, from quiet nature preserves to vibrant island communities. And while you never know where your trip will take you, rest assured that there’s a multitude of wonderful anchorages that won’t disappoint.
Deer Isle and the Surrounding Archipelago
The first day of sailing might take you through the Deer Isle archipelago—a chain of more than 50 islands scattered just off the coast. Many are protected by organizations like the Maine Coast Heritage Trust and the Maine Island Trail Association, preserving their wild beauty for generations to come. These are secret slices of Maine, reachable only by boat. You’ll see kayakers, lobster boats, and windjammers—and not much else other than the rugged pine-covered shores and the eagles that sore above them.
Some of our favorite stops? Russ Island, McGlathery Island, and Camp Island—perfect for beachcombing, rock-skipping, and maybe even a lobster bake right on shore.
For a glimpse of an authentic Maine fishing village, windjammers often stop at the town of Stonington, located on Deer Isle itself. With a lobster fleet that lands more pounds than any other town in the state, Stonington is the heart of Maine’s lobster industry. But it’s also home to artists, nature lovers, and small business owners who give the town its eclectic, creative spirit. Stroll through and you’ll find art galleries, cozy cafés, and even the Stonington Opera House.
Isle au Haut: Remote & Radiant
At the southern end of the archipelago is Isle au Haut, one of the more remote stops on a Windjammer cruise. It was named by Samuel de Champlain in the 1600s. Today, it’s home to a year-round population of just 54, swelling to around 250 in summer as visitors seek out its trails and tranquil shores. Much of the island is part of Acadia National Park, offering dramatic vistas and rugged hiking routes. Meandering through town you’ll find the postcard-perfect post office and views of the island’s lighthouse.
Castine & Holbrook Island: History Meets Nature
Later in the trip, the captain might sail north up Penobscot Bay. You may drop anchor at Holbrook Island—a pristine nature preserve just off the coast of Castine. The island features peaceful hiking trails and serves as a nursery for harbor seals. Keep your eyes out for pups lounging on the rocks or darting through the water.
Nearby Castine is a town steeped in history. Long a gathering place for Native Americans, it later played a key role in colonial conflicts. You can still visit the ruins of Fort George, built during the Revolutionary War. Today, Castine is also home to the Maine Maritime Academy, giving this quiet coastal town a deep connection to seafaring heritage.
Buck’s Harbor: Quiet Beauty in South Brooksville
While not on an island, Buck’s Harbor in South Brooksville is a favorite anchorage for Windjammer captains and guests. This peaceful inlet offers a sense of serenity and seclusion, surrounded by the peninsula’s bluffs. The very protected waters have some of the warmest waters in the bay (sometimes 70 degrees!) so be sure to have the captain put down the swim ladder so you can take a plunge!
The nearby village gives a glimpse into traditional coastal life—quiet, welcoming, and utterly charming. You may recognize it if you ever read “One Morning in Maine” by Robert McClosky as a kid. Little Sal and Jane head to Condon’s Garage in this town to get their outboard motor fixed. Condon’s still stands!
North Haven & Burnt Island: Final Night Magic
On your final night, you might find yourself anchored at North Haven, one of the larger islands in Penobscot Bay. Its scenic trails, galleries, and friendly village atmosphere make it a wonderful place to unwind. You might visit North Haven Village with its local coffee shop, art spaces, and tight-knit community feel.
Or your captain may head for Pulpit Harbor, a favorite among Windjammer guests. The harbor is guarded by a rocky entrance and a towering osprey nest—one that’s been noted by explorers as far back as Champlain. Inside, calm waters and brilliant sunsets await.
Just off North Haven lies Burnt Island, part of the North Haven Conservation Partners’ protected lands. It’s a peaceful, scenic spot that’s often a trip favorite—perfect for a quiet walk or a lobster bake.
These are just a few of the island gems you might visit on a Maine Windjammer adventure. In our next blog post, we’ll reveal a few more!
Category: The Maine Coast
