Did you know that Casco Bay is home to an astonishing 785 islands and exposed ledges, despite spanning just 229 square miles of water? Often called the “Calendar Islands” because folklore suggested you could explore a different island every day of the year, this coastal gem offers an unparalleled maritime playground for visitors. With only 14 of these islands inhabited, Casco Bay presents a perfect blend of accessible attractions and untouched natural beauty waiting to be discovered.
Getting to Casco Bay, Maine
Casco Bay sits along Maine’s southern coast, with Portland serving as its primary gateway. Most visitors arrive via Portland International Jetport, which offers direct flights from major East Coast cities. Alternatively, Amtrak’s Downeaster train provides scenic rail service from Boston to Portland, making it an excellent option for those preferring to avoid air travel.
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From Portland, accessing the islands requires a short ferry ride. The Casco Bay Lines ferry service operates year-round, connecting Portland to the major inhabited islands including Peaks, Great Diamond, Little Diamond, Long, Chebeague, and Cliff Islands. During summer months, additional private water taxi services offer more flexible scheduling options for island-hopping adventures.
Best Time to Visit Casco Bay
Casco Bay experiences distinct seasonal changes, each offering a unique perspective on this coastal paradise. Summer (June-August) brings warm temperatures between 70-85°F, making it ideal for swimming, boating, and beach activities. This peak season offers the fullest range of tours, dining options, and island services, though accommodations should be booked well in advance.
Fall (September-October) transforms the islands with spectacular foliage while maintaining relatively mild temperatures. This shoulder season offers fewer crowds and reduced rates while still providing access to most attractions. Spring (May-early June) brings renewal to the bay with wildflowers and returning wildlife, though waters remain quite cold for swimming.
| Season | Temperature Range | Crowd Levels | Advantages | Considerations |
| Summer (Jun-Aug) | 70-85°F | High | Full services, warm water, extended daylight | Higher prices, advance booking needed |
| Fall (Sep-Oct) | 50-70°F | Moderate | Foliage, fewer tourists, lower rates | Cooler waters, some services reduced |
| Winter (Nov-Mar) | 20-40°F | Very Low | Authentic local experience, lowest rates | Limited services, cold conditions |
| Spring (Apr-May) | 45-65°F | Low | Wildflowers, wildlife, peaceful atmosphere | Cold water, variable weather |
Winter (November-March) offers a dramatically different experience with temperatures often below freezing. While many seasonal businesses close, year-round island communities provide an authentic glimpse into coastal Maine life. The reduced ferry schedule and weather considerations make winter visits best for those seeking solitude and a genuine local experience.
Top Attractions in Casco Bay
Portland Head Light
Commissioned by George Washington in 1791, Portland Head Light stands as Maine’s oldest lighthouse and one of the most photographed in America. Located in Fort Williams Park in Cape Elizabeth, this iconic beacon offers spectacular views of Casco Bay’s entrance. The adjacent museum, housed in the former keeper’s quarters, showcases the lighthouse’s rich history through artifacts and exhibits. The surrounding park provides picnic areas, walking trails, and historic fort ruins to explore.
Peaks Island
Just a 20-minute ferry ride from Portland, Peaks Island offers a perfect day trip or extended stay. Once known as the “Coney Island of Maine” for its amusement parks and entertainment venues, today’s Peaks Island presents a more relaxed atmosphere. Rent a bike from Brad’s Island Bike Rentals to circumnavigate the 4-mile perimeter, visit the Fifth Maine Regiment Museum, or relax on sandy beaches with stunning bay views.
Mailboat Run Cruise
Experience Casco Bay like a local aboard the historic Mailboat Run, the oldest operating boat mail delivery service in the United States. This working boat delivers mail and freight to the islands while offering passengers spectacular views and authentic island culture. The 2-3 hour narrated cruise visits several islands, providing a comprehensive introduction to Casco Bay’s maritime heritage.
Experience Casco Bay’s Maritime Heritage
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Fort Gorges
This Civil War-era granite fortress sits on Hog Island in Casco Bay, accessible only by private boat or kayak tour. Built between 1858 and 1864 but never garrisoned, Fort Gorges offers a fascinating glimpse into military history. Visitors can explore the parade ground, underground passages, and gun emplacements while enjoying panoramic views of Portland and the surrounding bay.
Eagle Island State Historic Site
Once the summer home of Arctic explorer Admiral Robert E. Peary, Eagle Island offers a fascinating museum dedicated to his North Pole expeditions. The island features trails through spruce forests, opportunities for wildlife viewing, and stunning panoramic vistas. Access is by private boat or tour service from Portland or Harpswell.
Island Hopping in Casco Bay
With hundreds of islands dotting Casco Bay, island hopping offers one of the most rewarding ways to experience this maritime wonderland. Each inhabited island has its own distinct character and attractions worth exploring.
Long Island
Home to approximately 200 year-round residents, Long Island offers beautiful beaches, including the popular Sandy Beach, and miles of walking trails through conservation areas. The island’s working harbor provides a glimpse into Maine’s lobstering tradition, while local establishments like Byers & Sons Market offer authentic island refreshments.
Great Diamond Island
Once a military outpost, Great Diamond Island now houses Diamond Cove, a private residential community built around the restored Fort McKinley. Visitors can dine at Diamond’s Edge Restaurant, explore historic military buildings, and enjoy the island’s peaceful walking paths. The absence of cars contributes to the tranquil atmosphere.
Chebeague Island
Casco Bay’s largest island, Chebeague (pronounced “sha-beeg”) offers a 9-hole golf course, sandy beaches, and the historic Chebeague Island Inn. The island’s rich maritime history is evident in its architecture and working waterfront. Bicycling remains the preferred method for exploring this 5-mile-long island.
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Cliff Island
The most remote of Casco Bay’s year-round islands, Cliff Island maintains a small community of about 60 residents. Its unspoiled beaches, nature preserves, and absence of tourist infrastructure appeal to those seeking an authentic Maine island experience. The Cliff Island Store & Café provides essential provisions and local flavor.
Water Activities in Casco Bay
Surrounded by water, Casco Bay naturally excels in aquatic adventures. From leisurely sailing excursions to active water sports, the bay offers activities for every interest and skill level.
Kayaking & Paddleboarding
Explore Casco Bay’s protected waters and hidden coves by kayak or paddleboard. Companies like Maine Island Kayak Co. and Portland Paddle offer guided tours suitable for beginners and experienced paddlers alike. Popular routes include circumnavigating Peaks Island, exploring the Fore River, and paddling to Fort Gorges for a unique perspective on this historic structure.
Sailing & Boating
Experience Casco Bay under sail aboard one of Portland’s historic schooners. The Maine Sailing Adventures and Portland Schooner Company offer daily sailing trips ranging from 2-hour harbor cruises to full-day excursions. For those preferring motorized exploration, numerous charter companies provide private boat rentals and guided tours of the bay’s highlights.
Fishing Charters
Casco Bay’s productive waters support diverse marine life, making it an excellent fishing destination. Species including striped bass, bluefish, mackerel, and groundfish can be targeted on half-day or full-day charters. Companies like Casco Bay Custom Charters provide all necessary equipment and expertise for a successful fishing adventure.
Dive Into Casco Bay Adventures
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Where to Eat in Casco Bay
Casco Bay’s culinary scene celebrates Maine’s maritime bounty with an emphasis on fresh seafood and locally-sourced ingredients. From upscale waterfront restaurants to casual island eateries, dining options abound throughout the region.
Portland Waterfront
Portland’s working waterfront hosts numerous acclaimed restaurants specializing in seafood and contemporary cuisine. Establishments like Eventide Oyster Co., Street & Co., and Scales offer innovative preparations of local seafood in atmospheric settings. For the quintessential Maine experience, Portland Lobster Company serves fresh lobster rolls on their waterfront deck with live music during summer months.
Island Dining
Each inhabited island offers unique dining experiences worth the ferry ride. The Inn on Peaks Island combines pub fare with water views, while Diamond’s Edge Restaurant on Great Diamond Island occupies a historic naval building with elegant seafood offerings. The Chebeague Island Inn presents refined coastal cuisine with ingredients from their kitchen garden and local purveyors.
Casual Eats
For casual dining, island markets and cafes provide authentic local flavor. The Peaks Café offers breakfast sandwiches and baked goods, while the Cliff Island Store & Café serves homemade soups and sandwiches. On the mainland, food trucks and casual seafood shacks like The Lobster Shack at Two Lights in Cape Elizabeth provide delicious, unfussy meals with spectacular views.
Where to Stay in Casco Bay
Accommodations in Casco Bay range from luxury waterfront hotels to charming island inns and vacation rentals. Your choice of lodging will significantly shape your Casco Bay experience, with each option offering distinct advantages.
Island Accommodations
For an immersive Casco Bay experience, consider staying on one of the inhabited islands. The historic Chebeague Island Inn offers refined accommodations with ocean views, a restaurant featuring local ingredients, and a 9-hole golf course. The Inn at Diamond Cove provides luxury accommodations in restored military officers’ quarters on Great Diamond Island, while the Inn on Peaks Island offers six comfortable rooms above their popular restaurant and bar.
Find Your Perfect Casco Bay Retreat
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Portland Waterfront Hotels
Portland offers numerous hotels with easy access to Casco Bay ferries and attractions. The Portland Harbor Hotel provides upscale accommodations in the heart of the Old Port district, while the Press Hotel offers boutique lodging in the former Portland Press Herald building. For harbor views, consider the Residence Inn Portland Downtown/Waterfront or the AC Hotel Portland Downtown/Waterfront.
Vacation Rentals
For families or extended stays, vacation rentals provide space and amenities not found in traditional accommodations. Numerous cottages, homes, and apartments are available on Peaks, Long, and Chebeague Islands, offering authentic island living experiences. Mainland options in Portland, South Portland, and Cape Elizabeth provide convenient access to both urban amenities and island ferries.
Practical Tips for Visiting Casco Bay
Transportation Tips
Casco Bay Lines ferries serve as the primary transportation to the islands, with schedules varying seasonally. During summer months, advance ticket purchases are recommended, especially for weekend travel. Most islands have limited or no car access, so plan accordingly. Bicycles can be transported on ferries for an additional fee and provide an excellent way to explore the larger islands.
Island Etiquette
When visiting the islands, remember you’re entering small communities where residents live year-round. Respect private property, stay on designated paths, and pack out all trash. Many islands have limited or no public restrooms, so plan accordingly. Support local businesses when possible, and be mindful that services may be limited, especially in off-peak seasons.
Weather Considerations
Casco Bay weather can change rapidly, with fog being particularly common during summer mornings. Pack layers regardless of season, and always bring rain gear and sun protection. Ferry cancellations due to severe weather are possible, so maintain flexibility in your plans and check the Casco Bay Lines website for service updates before traveling.
Are there public restrooms on the islands?
Public restroom facilities are limited on most islands. Peaks Island has public restrooms near the ferry landing and at the Fifth Maine Regiment Museum. On other islands, facilities may be available at restaurants or museums when open. Plan accordingly and always respect private property.
Can I bring my car to the islands?
Vehicle access is extremely limited. Only Peaks Island and Chebeague Island accommodate vehicles, and ferry reservations for cars must be made well in advance (often months ahead in summer). Most visitors explore the islands on foot or by bicycle, which can be brought on ferries for a small fee.
Are there grocery stores on the islands?
Most inhabited islands have small markets with basic provisions, though prices may be higher than mainland stores. Peaks Island has Hannigan’s Market, Long Island features Byers & Sons Market, and Cliff Island has the Cliff Island Store. For extended stays, consider bringing supplies from Portland’s markets.
Plan Your Casco Bay Adventure
From the historic lighthouses guarding its entrance to the peaceful island communities dotting its waters, Casco Bay offers a quintessential Maine experience that combines natural beauty, maritime heritage, and authentic coastal culture. Whether you’re kayaking around secluded islands, sampling fresh seafood at waterfront restaurants, or simply relaxing on an island beach, Casco Bay creates memories that linger long after your visit ends.
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With its perfect blend of accessibility and unspoiled beauty, Casco Bay invites you to discover why generations of visitors have fallen in love with this extraordinary corner of coastal Maine. Whether you have a weekend or a week, the islands, lighthouses, and welcoming communities of Casco Bay promise an authentic New England experience that will call you back season after season.
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