The Best Maine Islands to Explore Off Portland’s Coast

Maine’s stunning natural beauty and rich history attract tourists from all over the world. While the mainland offers plenty of attractions and amenities, it’s also worth exploring the nearby islands, which are truly breathtaking. In this local travel guide, we will highlight some gems of the islands around Portland, Maine. Whether you’re a local or a visitor, this guide will help you make the most of your Maine islands adventure!

Little Diamond Island

Little Diamond Island features a yacht club, hiking trails, and a beach. This island was used in the 1800s to quarantine immigrants with contagious diseases. Today, it is an exclusive residential island with beautiful views and stunning homes. You can take a stroll around the island or enjoy a picnic on the beach. Find the perfect picture-perfect spot and capture lasting memories of your experience.

Peaks Island

Located just 3 miles from Portland, Peaks Island is the most visited island on Casco Bay. This island has a unique vibe with its colorful houses, art galleries, and shops. Rent a bike, take a walk or hop on a free shuttle around the island and explore its hidden spots. From the Battery Steele World War II relic to the brave Atlantic waters off of “The Point”, this island offers something for everyone.

Long Island

Long Island is about 6 miles from Portland. This island features a sandy beach, a lighthouse, and a winery. Take a tour of the Seven Islands Farm, visit the marine museum, or simply soak up the sun and enjoy the pristine beaches. It’s easy to find tranquility and peace on Long Island away from the bustle of city life.

maine islandsGreat Diamond Island

Great Diamond Island was once a military fort and served as a hospital during the Civil War. You can take a self-guided tour of the fort or visit the museum, which has an exhibit on the history of White’s Cove and its shipbuilding industry. The island also presents a wonderful getaway to couples looking for a romantic experience. 

Come celebrate Flappy Hour with Sail Portland Maine! We offer unique chartered sails out to the stunning Crown Jewel restaurant aboard the beautiful Calista Ann, our motored picnic boat. Round trip fare includes a guaranteed reservation at the restaurant and an hour of dining (or 1.5 hours for brunch). All our charters depart from Fore Points Marina, located conveniently in downtown Portland. Reservations for the Flappy Hour sails fill up quickly, so book your trip with us today!

Chebeague Island

Chebeague Island is the biggest island in Casco Bay, at almost 4 miles long. This island features stunning coastal views, a golf course, and a beautiful inn. The island has preserved natural beauty, charming shops, and galleries for visitors to enjoy unique pieces of art. You can rent a bike or car to explore the island’s beaches, forests, and wildlife.

Explore Maine’s Islands with Sail Portland Maine 

Exploring the beautiful islands off Portland, Maine’s coast is an experience that travelers should not miss. Traveling around on Sail Portland Maine can be a fun, unique way to do so. These islands offer a unique, peaceful, and adventurous getaway, rich in American history. The sights, sounds, and experiences will leave a lasting impression, making you want to return for many years to come. So why wait? Book a chartered cruise on Casco Bay with Sail Portland Maine today to explore all that these beautiful islands have to offer.