Portland, Maine: Coastal Windjammer Sailing Cruise

Top rated
4.7 out of 5 stars
4.7
51 reviews
Activity provider:
Portland Schooner Co.
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Portland, Maine: Coastal Windjammer Sailing Cruise
Top rated
4.7 out of 5 stars
4.7
51 reviews

Glide through the pristine waters of Casco Bay on Bagheera, Wendameen, or Timberwind sailing ships, and experience Maine's historic craftsmanship on this sailing 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 out of 5 stars
W
William – United States

Always a great day on a sailboat on a breezy day...

5 out of 5 stars
Y
Yogesh – United States

It was an excellent experience and the crew was amazing!

Select participants and date

Itinerary

  • Starting location:

    56 Commercial St

  • Casco Bay

    Sailing (2 hours)

  • Arrive back at:

    56 Commercial St

Main sites passed

For reference only. Itineraries are subject to change.

Highlights

  • Enjoy a peaceful coastal getaway on the tranquil waters of Casco Bay
  • Take in the beauty of a Portland, Maine from a unique vantage point
  • Experience a delightful cruise that promises fun for the entire family
  • Pack a picnic lunch along with your favorite soft drink, wine, or beer
  • Pack a picnic dinner along with your favorite soft drink, wine, or beer

Full description

Experience the beauty of Portland, Maine's rugged coastline on a historic windjammer sailing ship in Casco Bay. Sail by lighthouses, seals, and seabirds as you feel the wind in your hair. Learn how the wooden windjammer you are sailing on was built in Maine and is listed on the National Register of Historic Places.

Pack a meal, bring your favorite wine or beer, and sit back and relax as you slip through the pristine waters of Casco Bay. Let your skipper take charge and take in the marine wildlife and views surrounding you. See Portland from a unique vantage point.

Have fun with the whole family or with friends on a day out at sea, before heading back to port.

Includes

  • Windjammer cruise
  • Life jackets
  • Food and drinks (Bring Your Own)
  • Tips
  • Group Narration (our captain and crew are happy to answer questions about the harbor sights, wildlife, or sailing, but we do not narrate the sail)

Meeting point

Check in for your cruise on the Maine State Pier. Go past Gate 5 for the Casco Bay Ferry to the dock house on the right.

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Important information

Know before you go

  • There is an environmentally friendly marine composting toilet onboard

From $67 per person

Customer reviews

Overall rating

4.7 /5
4.7 out of 5 stars

based on 51 reviews

Review summary

  • Guide
    5/5
  • Transportation
    4.9/5
  • Value for money
    4.7/5

Customer photos

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5 out of 5 stars
W
William – United StatesJuly 18, 2025 – Verified booking
Always a great day on a sailboat on a breezy day...
5 out of 5 stars
Y
Yogesh – United StatesJune 1, 2025 – Verified booking
It was an excellent experience and the crew was amazing!
5 out of 5 stars
K
Kaitlyn – United StatesOctober 23, 2024 – Verified booking
We had a beautiful, relaxing sail. The captain & crew were very friendly and knowledgeable about the area. Each one made sure to talk to everyone on the boat and make sure we had a good time.

Product ID: 722259

Activity provider:
Portland Schooner Co.

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