Portland, Maine: Sunset Windjammer Cruise Along the Coast

Top rated
4.7 out of 5 stars
4.7
79 reviews
Activity provider:
Portland Schooner Co.
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Portland, Maine: Sunset Windjammer Cruise Along the Coast
Likely to sell out
Top rated
4.7 out of 5 stars
4.7
79 reviews

Glide through the pristine waters of Casco Bay on Bagheera, Wendameen, or Timberwind sailing ships, and experience Maine's historic craftsmanship on this boat tour in Portland.

About this activity

Free cancellation
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Duration 2 hours
Check availability to see starting times
Host or greeter
English

Highlighted reviews from other travelers

5
5 out of 5 stars
D
Dora – United States

Loved the peacefulness of the sail. Boat was amazing. Captain Jack and his 1st mate did an excellent job. Recommend bringing a picnic basket and a jacket.

5
5 out of 5 stars
K
Kathy – United States

It was very enjoyable. Crew was so knowledgeable and answered questions with a smile. We would do it again. . Thanks guys!

Select participants and date

Itinerary

  • Starting location:

    56 Commercial St

  • Casco Bay

    Sailing (2 hours)

  • Casco Bay

    Sunset

  • Arrive back at:

    56 Commercial St

Main sites passed

For reference only. Itineraries are subject to change.

Highlights

  • Watch the sunset as you enjoy a picnic dinner on a sailboat
  • Enjoy a peaceful, coastal experience on the calm waters of Casco Bay
  • Take in the beauty of Portland, Maine from the water
  • Experience a delightful cruise that promises fun for the entire family
  • Pack a picnic dinner along with your favorite soft drink, wine, or beer

Full description

Step onboard a historic schooner, some of which are over 100 years old, and set sail on Casco Bay in Portland, Maine. Help the boat crew hoist the sails or even get behind the wheel.

Step into history aboard a locally-built wooden windjammer, with three of these vessels listed on the National Register of Historic Places. Experience the beauty of the rugged coastline, complete with a beautiful sunset, lighthouses, seals, and seabirds.

Pack a meal, bring your favorite wine or beer, and sit back and relax as you slip through the pristine waters of Casco Bay.

Includes

  • Cruise
  • Life jackets
  • Food and drinks (you can bring your own)
  • Tips

Meeting point

Go to the Maine State Pier, past Gate 5 of the Casco Bay Cruise Lines to the end of the wharf. You will see a small dock house where you will check in 30 minutes before your departure.

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Likely to sell out

From $75 per person

Customer reviews

Overall rating

4.7 /5
4.7 out of 5 stars

based on 79 reviews

Review summary

  • Guide
    4.8/5
  • Transportation
    4.9/5
  • Value for money
    4.6/5

Customer photos

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5
5 out of 5 stars
D
Dora – United StatesJuly 2, 2025 – Verified booking
Loved the peacefulness of the sail. Boat was amazing. Captain Jack and his 1st mate did an excellent job. Recommend bringing a picnic basket and a jacket.
5
5 out of 5 stars
K
Kathy – United StatesJune 16, 2025 – Verified booking
It was very enjoyable. Crew was so knowledgeable and answered questions with a smile. We would do it again. . Thanks guys!
5
5 out of 5 stars
N
Nina – United StatesJune 8, 2025 – Verified booking
A beautiful way to spend our last sunset in Maine! When all the passengers started to gather at the pier, I began to worry that it was going to be difficult to truly enjoy the boat trip. I was wrong! It was so exciting to see the crew and volunteers raise the sails. The boat is just beautiful and the bay was so peaceful. An amazing activity for our family. I’m so happy we decided to do it. I would book this again in a heartbeat.

Product ID: 708217

Activity provider:
Portland Schooner Co.

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