7 Days of Island Hopping in Casco Bay
Begin your island-hopping adventure in Portland, Maine, your gateway to Casco Bay. The city’s bustling Old Port district is not only a hub of historic charm and local cuisine but also the launching point for your journey. Ferries to Casco Bay’s islands depart from the Casco Bay Lines terminal, conveniently located near Portland’s waterfront. With frequent departures and a year-round ferry, you’ll find it easy to explore the unique offerings of each island.
Day 1
Peaks Island
Photo Credit: Kirsten Alana Photography
Photo Provided by Inn on Peaks Island
Approximate travel time from Portland: 17 minutes one-way
Before you set sail, take time to settle-in and explore Portland’s Old Port, with its cobblestone streets and lively waterfront. Enjoy a morning coffee at a cozy local coffee shops + tea houses. Wander through charming boutiques, savoring the historic ambiance of this vibrant district. Outdoor dining options oceanside or in the middle of the action downtown offer fresh lobster dinners and seafood towers that capture the essence of Maine’s culinary heritage.
Upon arrival on Peaks Island, immerse yourself in the island’s small-town charm. Rent a bike or golf cart, taking in the scenic route. There are a few spots to grab a souvenir or an ice cream. There are two public beaches available for visitors to explore. A sand beach is located on the southwest part of the island, where you can kayak out to Catnip Island. Enjoy stunning views on Cairn Beach, located on the backshore. For lunch, join one of the only public lobsterbake’s in the region at Island Lobster Co. for some authentic Maine eats.
Head over to Inn on Peaks, where you can enjoy some local drink classics with a twist. Indulge in thoughtfully-crafted drinks like a refreshing blueberry float or a Casco Bay Spritz, a blend of Prosecco, elderflower, lemon, and mint. As the day winds down, catch the ferry back to Portland to continue soaking in the city’s vibrant atmosphere and nightlife.
Day 2
Great/Little Diamond Island
Approximate travel time from Portland: 15-25 minutes one-way (depending on route and cargo)
Start your day in Portland’s Arts District, where the rich cultural atmosphere sets the tone for your island adventure. Stroll through the district’s charming streets, marveling at the historic architecture and vibrant art galleries. Enjoy breakfast at a cozy, local café, savoring fresh pastries or a hearty breakfast to fuel your day. After soaking in the artsy vibe, make your way to the Casco Bay Lines terminal for your ferry ride to Great Diamond Island.
Upon arrival on Great Diamond Island, you’ll find a tranquil retreat from the city’s hustle and bustle. For a delightful lunch, head to the Diamonds Edge Restaurant and Inn on Diamond’s Cove, where you can enjoy fresh seafood and a relaxed, scenic dining experience. Afterward, take a leisurely to explore the island’s scenic trails, appreciating its unspoiled beauty.
Day 3
Long Island
Approximate travel time from Portland: 30-60 minutes one-way (depends on route and cargo)
Kick off your day with an early morning walk at one of Greater Portland’s hiking and walking trails. Just fifteen minutes south of Portland, for example, is the Scarborough Marsh where you can enjoy the tranquil beauty of Maine’s largest salt marsh. On your way back to Portland, grab a famous potato donut from The Holy Donut—a must-try local treat. And while you’re there make a quick stop at Len Libby Chocolatier for unique snacks and souvenirs. Stop and see their famous chocolate moose, Lenny, before heading to the ferry.
The ferry ride to Long Island can be up to an hour, giving you time to relax and enjoy the unfurling landscape as the ferry docks at other islands. Once you arrive, head to Byers & Sons Long Island Bakehouse, short walk from the ferry dock, for a hearty lunch featuring fresh, local ingredients. Taste-test pizza flavors and a variety of baked goods like brownies, cookies, and whoopie pies. Afterward, explore the island’s peaceful trails, beaches, and charming community, soaking in the island’s serene atmosphere.
Day 4
Chebeague Island
Approximate travel time from Portland: 60-90 minutes one-way (depends on route and cargo)
Start your day with a leisurely breakfast in Portland before setting off for Chebeague Island, one of Casco Bay’s largest and most captivating destinations. The ferry ride to Chebeague offers stunning views of the bay, setting the stage for a day of exploration and relaxation. As you approach the island, the landscape unfolds into a mix of sandy beaches, lush forests, and rolling meadows—a true retreat from the hustle and bustle of the mainland.
Once you arrive on Chebeague, begin your adventure with a stroll along the island’s quiet roads, where you’ll encounter historic homes and friendly locals who embody the island’s welcoming spirit. Make your way to the Chebeague Island Inn, a beautifully restored hotel that’s perfect for lunch or a refreshing drink on the porch, with panoramic views of the bay. The inn’s menu features fresh, locally sourced ingredients, offering a true taste of Maine’s coastal cuisine.
After lunch, explore the island’s natural beauty by visiting one of its secluded beaches or taking a hike along one of the many trails that crisscross the island. Whether you’re seeking a peaceful spot to read by the water or a scenic hike with breathtaking views.
Day 5
Bailey Island
Approximate travel time from Portland: 60 minutes one-way (drive time)
Start your day with a classic Maine road trip, beginning with a visit to Freeport, home of the iconic L.L.Bean flagship store. Spend your morning shopping for outdoor gear, local crafts, and unique souvenirs in Freeport’s charming village. Afterward, continue your journey up the scenic Harpswell Peninsula toward Bailey Island, a destination known for its breathtaking coastal views and rich maritime history.
Bailey Island is one of the few Casco Bay islands accessible by car, offering the perfect opportunity to explore at your own pace. Upon arrival, head to Cook’s Lobster & Ale House for a lunch that captures the essence of Maine’s local fare. Enjoy a lobster roll or fresh seafood while taking in the stunning views of the working harbor and the famous Cribstone Bridge, a marvel of engineering that connects Bailey Island to Orr’s Island.
Day 6-7
calendar Islands
As your island-hopping adventure draws to a close, there’s still so much more to explore in Casco Bay. We’ll even let you in on a local secret. Same call these scenic islands the Calendar islands, because when early explorers were still uncovering these paradises – some said there was an island for every day of the year. For the last few days of your trip, consider staying overnight on one of these thrilling island escapes to fully immerse yourself in the natural beauty of these coastal retreats in Maine.
Choose from any of the islands you’ve visited so far, or venture to new ones like Cliff Island, House Island, or Clapboard Island in Falmouth. Cliff Island, the smallest of Casco Bay’s year-round communities, offers a true off-the-beaten-path experience with its unspoiled landscapes and peaceful environment. No matter which island you choose, your final days in Casco Bay will be filled with the unforgettable charm and serene beauty that only these hidden gems can offer. Whether you spend your time exploring new trails, enjoying quiet moments by the water, or simply soaking in the breathtaking views, the Calendar Islands will leave you with lasting memories of Maine’s coastal paradise.
