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

(NOTE: This is NOT a narrated tour, but our crew is happy to answer any questions you have about the sites).

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

4.66

139 reviews

Total reviews and rating from Viator & Tripadvisor

106

It was a beautiful day...
Caroline T,
Aug 9, 2025
- Viator
4.00
It was a beautiful day sailing on Casco Bay. Too bad the winds weren’t cooperating enough to allow us to get closer to the Portland Head Light. Nonetheless, we enjoyed the unique tall ship experience and the views from the Bay. This is a non-narrated tour, so it’s up to you to ask questions if you are interested in learning about the sights. The crew is very friendly to answer them. While I never went below deck, sitting in the boat without a backrest got a little tiring after a while. Fortunately, the water was calm enough to stand up and walk around safely.
The crew was nice, but...
Susan V,
Aug 9, 2025
- Viator
2.00
The crew was nice, but offered no information about the area. They did say if we had questions to ask, but as a visitor, it would have been nice for them to share any information.
Really enjoyed sailing...
Tammy L,
Aug 8, 2025
- Viator
5.00
Really enjoyed sailing with this company . Didn’t have to listen to a play by play around the area! Very relaxing and enjoyable! We loved that we could bring our own food and drinks !
Fantastic experience!...
Ellen W,
Aug 5, 2025
- Viator
5.00
Fantastic experience! Easy sail around the bay on a gorgeous 100 year old sail boat, staff was super friendly and accommodating, byob made it all the more fun. Would absolutely do again!
Nice laid back sail...
Jacqueline D,
Aug 5, 2025
- Viator
5.00
Nice laid back sail around Casco Bay! It was a beautiful day but didn't have much wind so the Captain had to cheat a bit with the motor but it was still enjoyable.