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The Best of Maine's Island Life

Southern Maine boasts a collection of captivating islands that offer a perfect summer escape. With their picturesque landscapes, charming coastal towns, and mouthwatering cuisine, these islands provide an idyllic getaway for travelers seeking relaxation and adventure. Here are the best islands in Southern Maine to explore during the summer season.


1. Peaks Island


Just a short ferry ride from Portland, Peaks Island is a hidden gem that captures the essence of coastal Maine. With its laid-back atmosphere and captivating views, this island is perfect for a day trip or a longer getaway.


Must-See Locations:

  • Battery Steele: Explore the remnants of an old military fortification at Battery Steele. Climb on the massive concrete structures and take in panoramic views of Casco Bay.

  • Umbrella Cover Museum: Delight in the whimsical charm of the Umbrella Cover Museum, a one-of-a-kind institution that celebrates the beauty and diversity of umbrella covers.

  • Lion's Club Beach: Soak up the sun and enjoy a relaxing day at this picturesque sandy beach. Take a dip in the refreshing ocean waters or have a picnic with stunning waterfront views.

Restaurant Recommendations:

  • The Cockeyed Gull: Indulge in delicious seafood dishes, including lobster rolls and fish and chips, at this waterfront restaurant. Enjoy the lively atmosphere and stunning sunset views.

  • The Peaks Café: Savor homemade comfort food and delectable baked goods at this cozy café. Don't miss their famous blueberry pancakes, made with fresh Maine blueberries.

Fun Activities:

  • Golf Cart Tour: Explore the island's charming neighborhoods and scenic spots on a golf cart tour. Rent a cart and leisurely cruise around, enjoying the island's unique character.

  • Artist Studios: Peaks Island is home to numerous artists and craftsmen. Visit their studios and galleries to discover beautiful artwork, pottery, jewelry, and more.

  • Hiking and Biking: Take a leisurely stroll or bike ride along the island's winding roads, capturing the breathtaking coastal views at every turn.

2. Chebeague Island


Situated in Casco Bay, Chebeague Island offers a serene coastal experience with its unspoiled landscapes, sandy beaches, and charming community.


Must-See Locations:

  • Chandler's Cove: This scenic cove offers a tranquil setting for a peaceful beach day. Take a walk along the sandy shores, soak in the sun, and enjoy the cool ocean breeze.

  • Chebeague Island Inn: Visit this historic inn, dating back to the late 1800s, and revel in its timeless elegance. Take a guided tour, admire the stunning architecture, or savor a meal with a view at their on-site restaurant.

Restaurant Recommendations:

  • The Chebeague Island Inn Restaurant: Indulge in a fine dining experience at this renowned restaurant. Relish their seasonal menus featuring locally sourced ingredients, all while enjoying breathtaking views of the water.

  • Niblic: This charming café and bakery offers delectable pastries, sandwiches, and coffee. Grab a bite to eat, and don't forget to try their famous blueberry muffins.

Fun Activities:

  • Kayaking and Paddleboarding: Explore the island's coastline by renting a kayak or paddleboard. Glide through the calm waters, discovering hidden coves and marine life.

  • Island Bike Tour: Embark on a guided bike tour around the island, immersing yourself in its natural beauty and rich history. Learn about the island's past, visit notable landmarks, and enjoy the scenic views along the way.

3. Long Island


Located off the coast of Portland, Long Island offers a peaceful retreat with its pristine beaches, wooded trails, and charming community.


Must-See Locations:

  • Sandy Point Beach: Relax on the soft sandy beach, swim in the refreshing waters, or take a leisurely stroll along the shore. Enjoy panoramic views of the ocean and neighboring islands.

  • Long Island Community Library: Pay a visit to this quaint library, housed in a historic building dating back to the late 1800s. Browse through their collection, enjoy some quiet reading time, or participate in community events.

Restaurant Recommendations:

  • The Island Lobster Company: Feast on fresh, locally caught seafood at this rustic waterfront eatery. Delight in their lobster rolls, clam chowder, and other seafood delicacies while savoring the ocean views.

  • Island Market and Supply: This cozy market offers a variety of groceries, snacks, and prepared foods. Grab a delicious sandwich or picnic supplies to enjoy during your island exploration.

Fun Activities:

  • Nature Trails: Discover the island's natural beauty by hiking its scenic trails. Immerse yourself in the peaceful surroundings, observe wildlife, and enjoy panoramic views from various vantage points.

  • Beachcombing: Long Island is known for its picturesque beaches and abundant marine treasures. Take a leisurely stroll along the shore, collecting seashells, sea glass, and other fascinating beachcombing finds.



4. Great Diamond Island


Nestled off the coast of Portland, Great Diamond Island is a hidden gem in coastal Maine that offers a serene and picturesque getaway. With its pristine beaches, rich history, and breathtaking landscapes, this island is a perfect destination for those seeking tranquility and natural beauty. Let's dive into the delights that Great Diamond Island has to offer.


Must-See Locations:

  • Diamond Cove: Discover the island's historic heart at Diamond Cove. Explore the well-preserved military fortifications and enjoy scenic views of the harbor. Don't miss the Diamond Cove Music Festival, which showcases local talent in a charming outdoor setting.

  • Diamond Cove Beach: Unwind on the sandy shores of Diamond Cove Beach. Relax with a good book, take a refreshing swim in the crystal-clear waters, or simply bask in the sun while soaking up the island's peaceful ambiance.

Restaurant Recommendations:

  • Diamond's Edge Restaurant: Indulge in a delightful dining experience at Diamond's Edge Restaurant. Known for its creative and locally sourced cuisine, this waterfront eatery offers stunning views and a memorable culinary journey.

  • Crown Jewel: Located in a picturesque setting, this restaurant offers a fine dining experience that showcases the best of coastal Maine's flavors. From fresh seafood delicacies to expertly crafted dishes featuring local ingredients, the Crowned Jewel Restaurant delights the palate with its diverse and delectable menu.

Fun Activities:

  • Bike Rentals: Rent a bike and embark on a leisurely ride around the island. Cruise along scenic coastal roads, breathe in the fresh ocean air, and relish the peaceful surroundings.

  • Art Gallery Visits: Great Diamond Island is home to several art galleries, showcasing the works of local artists. Immerse yourself in the island's creative spirit by visiting these galleries and appreciating the diverse range of artistic expressions.



4. Isleboro

Located in the waters of Penobscot Bay, Isleboro is a serene and enchanting island that embodies the coastal charm of Maine. With its pristine beaches, lush landscapes, and welcoming community, Isleboro offers a tranquil retreat for those seeking relaxation and natural beauty. Let's explore the wonders of Isleboro together.


Must-See Locations:

  • Pendleton Point: Visit Pendleton Point, a scenic spot that offers panoramic views of the surrounding islands and the sparkling ocean. Take a leisurely walk along the trails, breathe in the fresh sea breeze, and capture stunning photographs of the coastline.

  • Turtle Head Preserve: Immerse yourself in nature's tranquility at the Turtle Head Preserve. This 330-acre preserve features well-maintained trails, beautiful forests, and captivating wildlife. Enjoy a peaceful hike, birdwatching, or simply find a serene spot to connect with nature.

Restaurant Recommendations:

  • The Islesboro Inn: Indulge in a delightful dining experience at The Islesboro Inn. This charming restaurant offers a menu that highlights fresh local ingredients, providing a taste of Maine's culinary delights. Enjoy your meal while taking in the picturesque views of the bay.

Fun Activities:

  • Biking: Explore the island's scenic beauty on two wheels. Rent a bike and pedal along the quiet roads, passing by charming homes, rolling fields, and breathtaking waterfront vistas.

  • Kayaking: Discover the coastal wonders surrounding Isleboro by renting a kayak. Paddle along the calm waters, explore hidden coves, and admire the rugged coastline.



These islands in Southern Maine provide an escape from the hustle and bustle of everyday life, offering a chance to unwind and immerse yourself in the coastal charm. From breathtaking views to delicious seafood and outdoor activities, these destinations have it all. So, plan your summer getaway to explore the beauty of Southern Maine's islands and create unforgettable memories along the way.


Note: Please check the availability and any restrictions of restaurants, activities, and transportation before your visit, as they may be subject to change. Stay informed and prioritize your safety and the safety of others.

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