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Casco Bay
Casco Bay

Casco Bay

Portland, Maine

The Basics

Keep an eye out for birds, seals, and the occasional whale while you hike along the coast, sail through the harbor, or hop on the ferry to visit Casco Bay’s seven accessible islands.

Most bay tours leave from nearby Portland, Maine’s capital city, and sometimes include a city tour along with a coastal sightseeing excursion. You can also opt for a private charter vessel in order to see Casco Bay’s lighthouses and historic forts at your own pace.

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Portland Tall Ship Cruise on Casco Bay
Portland Tall Ship Cruise on Casco Bay
star-4.5
$75.16 per adult
Traveler Favorite
Great sailing in Casco Bay!
October 19, 2021 we ventured out and took a trip on Casco Bay. We can’t brag enough on the crew of the Timberwind! Sean, Chuck, Feona and Sarah were fantastic! They are all very knowledgeable about the area and the sailing vessel. We learned so much and enjoyed the trip out to the area by Portland Head Light Lighthouse. We had great wind and the crew worked hard - we even helped a little when raising the sails. We highly recommend this trip.
Rodney_W, Oct 2021

Recent reviews from experiences in Portland

star-5
Wonderful
Lawrence_W, Oct 2021
Portland Tall Ship Cruise on Casco Bay
The beautiful day and wonderful crew made this a great trip. Watching the sails raising and filling with the wind was exciting
star-5
Good time
Michael_H, Sep 2021
Portland Tall Ship Cruise on Casco Bay
This was a lot of fun, great way to see Portland harbor and surrounding area. Crew were great, would do again.
star-5
A great way to see Portland
christen_t, Sep 2021
Portland Tall Ship Cruise on Casco Bay
The boat trip was wonderful! The captain and crew were very kind and professional. The weather was perfect.
star-4
Great day on the water!
Linda_S, Sep 2021
Portland Tall Ship Cruise on Casco Bay
The weather was perfect and the staff was very knowledgeable. had a difficult time finding them because the confirmation and tickets did not identify them as part of Portland schooner company. It listed as Wow a Tour and there were no identifying signs with this tour name. Once we found everyone, it was terrific.
star-5
Hoist the sails
Keith_M, Sep 2021
Portland Tall Ship Cruise on Casco Bay
Sunny weather..great crew and captain. Everyone on the ship ( crew and customers) were enjoying each other’s company. Totally recommend this adventure.
star-5
Great sailing experience!
Doreen_D, Aug 2021
Portland Tall Ship Cruise on Casco Bay
Captain and crew were great. The ride was fun. We we're able to help bring up the sail, which made for a different experience. I would highly recommend this cruise.
star-4
Relaxing sail
Greg_G, Aug 2021
Portland Tall Ship Cruise on Casco Bay
Sailing, helping to raise the sail. Would have liked more information on landmarks and history. Enjoyed meeting some of the other people.
star-5
Great time
Charles_S, Aug 2021
Portland Tall Ship Cruise on Casco Bay
Fun time. Professional crew. Even though mother nature did not cooperate, still a good time. Will definitely do again.
star-5
No wind
Terry_K, Aug 2021
Portland Tall Ship Cruise on Casco Bay
It was a good experience. We learned about the ship from the captain and crew. Unfortunately there was very little wind so we mostly motored not sailed. It was fun but I wish the crew would have pointed out points of interest as we traveled by.
star-4
Great cruise... Don't trust Karen...
Tabitha_C, Oct 2021
Portland Tall Ship Cruise on Casco Bay
It was an amazing experience once we got on the boat. Karen almost made us miss it all. Had a noon cruise and when we called for better directions to the dock house, when on our way, Karen said we had missed our 11am and she could bump us to 130.(Later I checked all emails... We received an email at 4am the day of the cruise changing our noon cruise to 11am!) She then gave us directions to the wrong boat where she greeted us and after she left the crew sent us to the other pier where our boat actually was. Karen was there to give us the tickets and instead of apologizing for the inconvenience she said "at least you got your walking in!" And laughed. My mother, post stroke, didn't need the extra walking. Thanks Karen. You're an inconsiderate brat. Do better. The 3 crew members made the actual cruise magical! Highly recommend. Just beware of ANY and ALL directions from Karen!
star-5
Great Trip!
Sharon_C, Jul 2021
Portland Tall Ship Cruise on Casco Bay
Loved the entire trip. The crew was great, interesting, informative and entertaining. Registration was easy. The only difficulty was finding the location of the ship. Some signs with arrows by the Casco Bay Lines Terminal could have been helpful. But all around a great trip! Looking forward to next time.
star-5
Outstanding crew and historic ship
DrWilliam_B, Jul 2021
Portland Tall Ship Cruise on Casco Bay
Outstanding crew, schedule and historic ship 👍👏 We will do it again in the near future. Hats off. Thank you

Things to Know Before You Go

  • Casco Bay is a must-see for nature and history lovers.

  • With relatively calm water conditions and multiple islands to explore, Casco Bay is a great destination for families with kids.

  • Remember to bring comfortable shoes and sun protection.

  • It’s a good idea to dress in layers, as the weather can change quickly in this coastal region.

  • Ferries from Portland to the islands in Casco Bay are accessible to wheelchairs and strollers.

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How to Get There

Casco Bay is located just north of Portland, Maine. Ferries operate daily between Portland and the islands of Casco Bay, and private charter vessels travel through the harbor as well.

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When to Get There

You can visit Casco Bay year-round, but summer is a lovely time, when the days are usually sunny and warm. Head out onto the water at dusk to see colorful sunsets over the bay.

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The Casco Bay Islands

Don’t miss Peaks Island, which is home to beaches, restaurants, and an art community, while Long Island is known for its hiking trails and conservation areas. Bailey Island is also a good hiking spot, while Diamond Cove (located on Great Diamond Island) is home to Fort McKinley—a structure designed to defend Portland Harbor during the Spanish-American War.

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