Windjammer Sail: Explore Casco Bay's Scenic Coastline

178 Ratings

Portland

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Sail Casco Bay on a historic Maine schooner. Enjoy lighthouses, seals, and seabirds. Bring your favorite drink and relax on this unique adventure.

Duration: 2 hours

Cancellation: 24 hours

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Highlights

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

What's Included

Life jackets

What's Not Included

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!

Additional Information

Join us for a delightful two-hour Windjammer Sail on Casco Bay in Portland, Maine — an ideal way to admire the stunning rugged coastline, featuring lighthouses, seals, and seabirds.
(NOTE: This is NOT a narrated tour, but our crew is more than happy to answer any questions about the sights).
Bring along a meal, your favorite wine or beer, and unwind as…

Location

56 Commercial St

Commercial Street

Please check your reservation to see the meeting point for your cruise. The Maine State Pier location: We are at the end of the Maine State Pier. Walk past Gate 5 of the Casco Bay Ferry to the dock house on the right-hand side to receive your tickets.

Cancellation Policy

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

Customer Ratings

4.6

(178 Ratings)

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K5859qrkarenp

Oct 13, 2025

First time on a Schooner - Best time ever! The Crew was very friendly and the Portland Harbor is beautiful! It was our first time on a Schooner and it didn’t disappoint!

Review provided by Tripadvisor

Altravelgal

Oct 10, 2025

A relaxing sail around the bay - This was a nice sailing experience! The captain and crew were very nice. If you have not experienced a schooner I would recommend this! They do just circle around the main part of the bay and although their website does highlight that you will see wildlife, it is highly unlikely to see any seals or get up close to the land on any part of the Bay tour.

Review provided by Tripadvisor

Sam

Oct 8, 2025

So nice - Very relaxing, the crew was really knowledgeable and friendly. Highly recommend this experience! We even for to see some seals which was the cherry on top.

Review provided by Tripadvisor

M6952makathleenp

Oct 5, 2025

Everything I hoped for! - It was everything I hoped for!!! The captain and crew were very friendly and knowledgeable and answered all of our questions. The boat was not too crowded. The sailing itself was so quiet and peaceful and being inside the bay meant the water wasn't too rough. Would highly recommend it!!

Review provided by Tripadvisor

Paul_y

Oct 4, 2025

Great view of Portland harbor - Crew did a great job of socializing with the riders and offering interesting information about the boat and their own path.

Review provided by Viator

Go764220

Oct 4, 2025

Relaxing cruise in the harbor - Beautiful and relaxing time on the water. It was a very mellow experience which made the setting even more enjoyable. The crew was friendly and accommodating and the boat was well maintained too.

Review provided by Tripadvisor

Donna_l

Oct 3, 2025

It is smooth sailing,... - It is smooth sailing, mild waves in the bay. And the crew, Noah, Lucas and Kyle made sure that the passengers were safe and comfortable. Impromptu history lessons were very much appreciated.

Review provided by Viator

Robert_g

Oct 3, 2025

Sailing the Portland Harbor. - Great tour of Portland harbor. Went out to near the Portland headlight (lighthouse). Good sailing day.

Review provided by Viator

Tan1950

Oct 3, 2025

Disappointing. - Disappointing. We just sailed back and forth in the harbor. I thought we would at least travel up and down the coast. Would not recommend.

Review provided by Tripadvisor

Pat_h

Oct 10, 2025

Not for kids!! - The crew was gracious and knowledgeable, but safety was lacking. It was an extremely windy day and they did not offer life jackets, which gave me pause for my six year old. Half way through, we caught a “rogue” wind gust which caused our boat to turn completely sideways and almost tip. One of the passengers went flying, breaking her arm and almost falling in. She was drenched and in distress, causing us to immediately return to shore. Had I not been holding tight onto my child, it would have been a terrifying situation. What was intended to be a two hour casual boat ride ended up being an extremely scary situation for my family. I would not recommend this for children whatsoever.

Review provided by Viator

Check Availability

From $67

up to 15 guests

1 - Adult