Set out on a journey to Maine’s enchanting islands, where the Atlantic’s rhythm touches shores of unparalleled beauty.
From the artist’s haven of Monhegan to the tranquil retreats of Chebeague and Vinalhaven, these ten islands offer a winning mix of serenity, natural splendor, and cultural heritage.
Discover hidden gems where mountains meet the sea, and the spirit of Maine is alive in every sunset and lighthouse beam! And if we leave you feeling inspired, consider joining us for one of our Day Tours in Portland, Maine, or Multi-Day Cycling Trips in Maine.
Campobello Island
Campobello Island, nestled in the Bay of Fundy, offers a serene escape with its rich history and natural beauty. While technically in Canada, its close ties to Maine and the story of its near-American past add to its intrigue.
The island is a hiker’s dream, with trails weaving through scenic landscapes, inviting visitors to explore its rugged beauty. The Roosevelt Campobello International Park, once the summer home of Franklin D. Roosevelt, stands as a testament to the island’s historical significance, offering glimpses into the past.
With attractions like the Mulholland Point Lighthouse and the chance to spot whales from its shores, Campobello Island merges natural wonders with historical charm, making it a unique destination for those seeking tranquility and a touch of adventure.
Campobello Island is part of the itinerary on our Bay of Fundy Multi-Sport Tour.
Islesboro Island
Islesboro Island, nestled off the coast of Maine, exudes an air of tranquility and exclusivity, accessible solely by ferry from Lincolnville. This slender island stretches 14 miles, akin to Manhattan’s length. It offers serene landscapes and ocean vistas at every turn. Despite its modest year-round populace of 500, which swells in summer, Islesboro retains a close-knit community vibe.
Attractions include the Islesboro Historical Society’s museum and the Grindle Point Sailor’s Museum and Lighthouse, enriching visitors with the island’s rich heritage and maritime lore. Islesboro’s natural beauty, enhanced by its limited but delightful dining options like The Dark Harbor Shop, makes it a quintessential Maine escape.
If you’d like to explore Islesboro Island on a guided tour, take our Sailboats and Summer Folk: Camden Bike Tour.
Frye Island
Frye Island offers a unique island experience within Sebago Lake, marked by its lush woodlands and a vibrant summer community. Frye Island’s lore includes the daring leap of Captain Frye, escaping adversaries with a bold swim to safety, a tale that echoes the island’s adventurous spirit. Established through a 1750 grant and later seceding to form its own town in 1998, Frye Island offers plenty of history and leisure opportunities.
The island’s landscape is dotted with homes overlooking Sebago Lake, accessible by a brief ferry ride, emphasizing its seclusion and allure. Frye Island epitomizes a laid-back lake lifestyle, making it a coveted destination for those seeking relaxation and adventure.
Peaks Island
Just a short ferry ride from Portland, Peaks Island maintains a distinct, relaxed atmosphere with a year-round population that cherishes its tight-knit community. Attractions like the whimsical Umbrella Cover Museum add to the island’s unique character, offering a glimpse into its playful spirit.
The island’s vibrancy is palpable during summer, with activities from biking to enjoying Reggae Sundays at Jones Landing encapsulating the perfect island getaway. Peaks Island serves not just as a retreat but as a lively hub within Casco Bay, offering a slice of island life that is both accessible and enchanting, a testament to Maine’s diverse island experiences.
You can cycle Peaks Island with Summer Feet by booking a place on our Pedal Peaks Island Tour.
Mount Desert Island
Mount Desert Island, a breathtaking expanse of 108 square miles, stands as the second largest island on the Eastern Seaboard and the crown jewel of Maine. It is home to the charming town of Bar Harbor and the majestic Acadia National Park. The island attracts over 2.5 million visitors annually, drawn by its natural splendor, where mountains kiss the sea, offering unparalleled vistas and outdoor adventures.
Acadia’s Cadillac Mountain offers awe-inspiring views, while Thunder Hole echoes the raw power of nature. Beyond the park’s 120 miles of hiking trails, Bar Harbor enchants with its eclectic mix of restaurants, galleries, and shops. Whether you’re an artist seeking inspiration or an adventurer chasing the next trail, Mount Desert Island provides an unforgettable backdrop for exploration and discovery.
Take our Maine’s Gold Coast Tour to discover the best Mount Desert Island has to offer!
Isle au Haut
Isle au Haut, an integral part of Acadia National Park, is a remote island that promises an authentic encounter with Maine’s wild landscapes. Accessible only by boat, this island offers a tranquil retreat for nature lovers and adventurers alike. With its rugged coastline, dense woodlands, and serene ocean vistas, Isle au Haut is a sanctuary where one can truly connect with the natural world.
The island’s trails wind through diverse ecosystems, leading hikers to secluded coves and quiet beaches untouched by time. For those seeking solace away from the bustling tourist spots, Isle au Haut provides a peaceful haven, embodying the untamed beauty of Maine’s islands. Whether it’s for a day trip or a more extended camping adventure, Isle au Haut invites visitors to immerse themselves in its pristine wilderness, offering a unique experience within Acadia National Park.
Chebeague Island
Chebeague Island, pronounced “shuh big,” is a testament to Maine’s enduring charm, stretching nearly five miles long and cradled within Casco Bay. This island, with its rich history of stone sloopers and granite trade, mirrors the state’s iconic imagery of rugged coastlines and towering pines. Today, Chebeague stands as a vibrant community, welcoming over 1,600 summer dwellers alongside its 360 year-round residents.
The island’s essence, captured in the simplicity of lawn games at the Chebeague Island Inn, bicycle rides along its shores, and leisurely beach days, invites visitors to step back in time. With activities that emphasize outdoor enjoyment and relaxation, Chebeague Island embodies the quintessential New England island life, making it a must-visit for those seeking to experience Maine’s unspoiled beauty.
Monhegan Island
Monhegan Island, a tiny, rocky enclave located ten miles off the mainland, is a bastion of unspoiled beauty and artistic inspiration. Known for its towering cliffs—the highest along the Maine coastline—Monhegan has captivated artists for over a century, fostering a vibrant colony where creativity flourishes. With no cars or paved roads, the island offers an escape to a simpler time, where the rhythm of the sea dictates life.
Its 12 miles of trails invite exploration, leading adventurers through wooded areas to breathtaking ocean vistas. Monhegan’s rich history, from its early days as a fishing camp to its role in the fur trade, adds depth to its allure. Today, the island continues to thrive on fishing while celebrating its artistic heritage, making it a haven for those seeking solitude and inspiration.
We enjoy the rugged beauty of Monhegan Island on our Penobscot Bay Multi-Sport Tour.
Squirrel Island
Squirrel Island, a quaint and secluded haven, offers a unique escape within Boothbay Harbor’s embrace. This mile-long sanctuary, shaped like its namesake, boasts a legacy as Maine’s oldest summer colony, cherished by generations of families. With over a hundred summer cottages, the island’s community thrives on tradition and simplicity, eschewing cars and bikes in favor of leisurely strolls along its paved sidewalks.
Visitors are encouraged to immerse themselves in the island’s serene lifestyle, exploring its post office, library, and canteen. Squirrel Island’s charm lies in its peacefulness and the opportunity it provides for quiet contemplation and reconnection with nature’s unadulterated beauty.
Vinalhaven Island
Nestled in Penobscot Bay, Vinalhaven Island emerges as a serene destination for those seeking respite from the hustle of modern life. Home to Maine’s largest year-round island community, Vinalhaven balances its working lobster fleet’s vitality with the tranquil allure of its natural preserves and swimming quarries.
Despite its popularity, the island maintains a laid-back atmosphere, inviting exploration of its rocky shores, tide pools, and sunset vistas. Outdoor enthusiasts will find solace in kayaking around the neighboring islets, hiking through the preserves, or bird watching. For a true taste of island life, a stop at Greet’s Eats for a lobster roll is essential. Vinalhaven’s understated charm and rich maritime culture earn it a place among New England’s most cherished hidden gems.
Maine’s islands offer a mosaic of experiences, from the artistic enclaves of Monhegan to the serene shores of Chebeague. Each island tells its own story, inviting travelers to discover Maine’s unparalleled natural beauty and rich maritime heritage.
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