Afternoon Windjammer Cruise Along the Coast of Portland Maine

Overview

Available languages

English

2 hours

Mobile ticket

Sail with us for a two-hour Windjammer Sail on Casco Bay in Portland, Maine — the perfect way to experience the beauty of the rugged coastline, complete with 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. All ages are welcome! Whether you are nine years old or 99, sailing aboard one of our Maine historic schooners is a unique adventure. All of our wooden windjammers were built in Maine and three are listed on the National Register of Historic Places.

Additional Info

Infants and small children can ride in a pram or stroller

Public transportation options are available nearby

Specialized infant seats are available

Suitable for all physical fitness levels

Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

What‘s Included

Life jackets

Food and Drink—But feel free to bring your own!

Group Narration - Our captain and crew are happy to answer questions about the harbor sights!

What To Expect

Casco Bay

Enjoy the beauty of the rugged coastline, complete with lighthouses and seals, as we slip through the pristine waters of Casco Bay.

•Admission Not Applicable

Options

Afternoon Windjammer Cruise Along the Coast of Portland Maine

Duration: 2 hours

Reviews

4.63

107 reviews

Total reviews and rating from Viator & Tripadvisor

Amazing experience....
Rosalis O,
Jul 15, 2025
- Viator
5.00
Amazing experience. Experienced crew, knowledgeable and amicable. They tour personnel was very attentive towards my back needs. Captain was very friendly as he shared many interesting stories. Thank you!
It was a great afternoon...
James J,
Jul 8, 2025
- Viator
5.00
It was a great afternoon of sailing! The crew and Captain were Great. Answered any question we had about the boat and sights we saw.
Great time
Rowena D,
Jul 7, 2025
- Viator
5.00
Fantastic experience. Great crew. Very knowledgeable about the area. Friendly and professional staff Loved how they let the cruises help with sails
Great Sail, Great Crew
Ignatios M,
Jul 6, 2025
- Viator
5.00
Excellent sail on a 101 year old Windjammer. Great and friendly crew and got to see almost the entire bay.
Timberwind provides memories of a lifetime.
James L,
Jul 3, 2025
- Viator
5.00
The experience of sailing the waters of Portland as they did centuries ago was truly amazing. Sailing the water was so relaxing to the soul. Taking in the beauty of the harbor and bay from aboard the Timberwind can not be topped. The Captain and his crew were professional and polite. The check in team were very helpful and polite also. We would recommend this to anyone visiting the area. Also, the sail was very smooth so we had no issues with motion sickness.