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Key Info

56 Commercial St.


Beaches, Parks and Gardens, Neighborhood/Area, Hiking, Recreation, Swimming/Pools, Shopping Type
Half Day to Full Day Time to Spend


  • 5.0Value
  • 0.0Food Scene
  • 5.0Atmosphere

Though beaches are few and far between in Portland, shorelines abound in the nearby Casco Bay Islands. The Casco Bay Islands are a group of islands located off the coast of Portland, six of which are accessible by ferry year-round. Each island has its own personality, history, attractions and activities.

Cliff Island, one of the smallest Casco Bay Islands, is home to only 60 residents year-round and is the only year-round island that features unpaved roads and as such, cars are seldom used. Meanwhile, Great Diamond, which was home to historic Fort McKinley, is lauded for its quintessential Maine landscape and boasts shallow, rocky shorelines backed by lush forests. Cars aren't allowed, so walking, biking or getting around on golf carts are the modes of transportation. You'll find plenty of beaches on this isle, specifically the stunning Diamond Cove, as well as a small museum, a bowling alley and tennis courts. You can make a weekend of it and stay at the Inn at Diamond Cove, which has a host of activities and excellent dining options.  

Chebeague Island is lauded for similarly attractive terrain, but retains a more storied history. The island is most famous for its stone sloopers – men that transported construction materials for 19th-century ships and many of the country's most notable structures, including the granite for the Washington Monument. Meanwhile, those unwilling to go too off the grid will enjoy amenity-packed Peaks Island, which features cafes, shops, museums and galleries in addition to beaches.

Recent travelers loved visiting the Casco Bay Islands. The pleasant ride along the bay's calm waters, the stunning ferry views, the lively narration (offered depending on ferry attendance) and the overall accessibility made this a memorable experience for many. Most travelers visit Peaks Island because it's the closest to Portland – only a 17-minute boat ride – however, others do recommend visiting other islands if you have the time. Travelers said those heading to Peaks Island should be aware that golf carts, the island's main source of transportation, are booked fast so you'll want to reserve one as soon as you get off the ferry. The Mailboat Run, the Casco Bay Line ferry that takes visitors along the daily route that drops off mail and freight to all the islands, is another popular tour option for travelers. Those passengers were quick to note, however, that the duration of the route varies greatly on the amount of products that need to be delivered to the islands.

Casco Bay Lines ferries are the most popular means of transportation for getting to the Casco Bay Islands. The company runs various types of tours seasonally, as well as single destination services. The Diamond Pass Run goes to Long Island, Peaks Island and Little and Great Diamond Island. The Mailboat Run travels to all the islands of Casco Bay except Bailey Island, which only sees tours during specific times of the year. All tour times vary depending on the island traveled to; Peaks Island is 17 minutes one way, while the Mailboat Run is about three-and-a-half hours round trip. It's important to note that some ferry routes do not allow passengers to get off at the islands, including the Mailboat Run. Fees and hours also depend on the island you're traveling to and the tour type. For more information about getting to the Casco Bay Islands, visit the Casco Bay Lines website.

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Time to Spend
#2 Old Port

Old Port is without a doubt the beating heart of Portland. This downtown neighborhood is considered the city's center and bustles with things to do left and right, all the while gracefully maintaining its historical facade. The area is lined with cobblestone streets and 19th-century warehouses, and with the wharf just steps away on Commercial Street, the city's heydays as a world-renowned port town are easily felt. Tourists can benefit from ferries and cruise experiences as well as the delectable catches that dock there daily.

Away from the waterfront, travelers will find plenty of options to sustain and entertain. Some of the city's most popular restaurants can be found in Old Port. Duckfat, Fore Street and Eventide Oyster Co., some of Portland's best dining spots, are within a three-block radius of one another. Though dining and shopping is spread out through the neighborhood, Congress Street is a great starting point; restaurants, boutiques, local art galleries and theaters line this thoroughfare. The edge of the Old Port neighborhood is also considered the beginning of the Arts District, which houses plenty of notable attractions, including the Portland Museum of Art, the Children's Museum & Theatre of Maine and the Portland Stage Company, to name a few.

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