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Portland, Maine Family-friendly activities

Our most recommended Portland, Maine Family-friendly activities

Portland: Schooner Tall Ship Cruise on Casco Bay

1. Portland: Schooner Tall Ship Cruise on Casco Bay

Set sail on a two-hour cruise from Portland along the rugged coast of Casco Bay. Pack a meal and your favorite wine or beer, and sit back and relax as you slip through the peaceful waters of Maine. Enjoy views of lighthouses, seals, and other coastal wildlife aboard a famous schooner tall ship. Join the crew to hoist the sails or take a turn at the ship's wheel if you feel inspired. Whether you're nine years old or 99, sailing aboard a Maine schooner is a unique adventure. Learn more about the wooden windjammers which are all listed on the National Register of Historic Places and were built in Maine.

Portland: Self-Guided Sightseeing Driving Audio Tour

2. Portland: Self-Guided Sightseeing Driving Audio Tour

Travel through the neighborhoods of Portland on a self-guided driving tour. Learn about the city’s history and culture from an audio-guided app on your smartphone and get panoramic views from the Eastern Promenade.  Start by downloading the app, which will function as your personal tour guide, audio tour, and map all in one. Once downloaded, your Portland tour begins at the Visit Portland Center. Drive down Commercial Street and hear about the industrial beginnings of the city. Along the way, you’ll see the wonderfully preserved Victoria Mansion, dating back to 1858. That’s followed by the even older Danforth Inn, which goes all the way back to 1823. As you drive up the Western Promenade, you’ll hear about some famous folks who were laid to rest in Portland, including the poet Henry Wadsworth Longfellow (a statue of whom you’ll see next, in Longfellow Square). Go to the Art District (perfect for picking up a souvenir), followed by a church that was once destroyed by the British.  Continue toward the shore, passing the site of an observatory that once guided ships into Portland’s occasionally treacherous harbor. Spot a couple of picturesque lighthouses perfect for any photo collection. Explore the Eastern Promenade, a 68-acre seaside park sporting plenty of unforgettable ocean views. You’ll see the strange and controversial “baked beans” building, before passing through Old Port again for a second chance to stop at one of the neighborhood’s many restaurants and boutiques. Pass by a statue of Portland’s own John Ford. Cross the Casco Bay Bridge into South Portland, home to a quieter community than its buzzing northern neighbor. Finally, you’ll arrive at Fort Williams Park, full of beauty and history. The tour concludes here.

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Other Sightseeing Options in Portland, Maine

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What people are saying about Portland, Maine

Definitely not a sailor so when the boat tilts it’s a bit disconcerting until you realize that’s what sailing is supposed to be. We apparently had real good wind on our trip so got to go out past where most end up. Very cool activity, got to see three lighthouses, some very cool houses along the coast and the rugged coast line without the drone of an engine. Captain and the other crew were knowledgeable and very cool, a nice peaceful adventure, definitely worth it in my book

This was the perfect way to end our Maine trip. Staff was friendly and knowledgeable and the boat itself was stunning. Learned A lot of history about the boat. My partner and I Loved every minute of it . Take advantage of the byob.

Really enjoyed learning about Portland. Easy to use. The directions were easy to follow.

Very relaxing! Lots of nice views! The crew is knowledgeable and funny!

Great sailboat rode around Casco Bay! Beautiful. Wonderful crew!