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Two hours sailing aboard a historic wooden schooner — enjoy the rugged Casco Bay coastline with views of lighthouses and marine life.
Set sail for a two-hour cruise along the stunning coastline of Casco Bay aboard a historic wooden schooner. This is not a narrated tour, but the crew is available to address any questions about the sights you'll encounter. You can expect to see lighthouses, seals, and seabirds during your time on the water.
Suitable for all ages, this experience invites guests to bring their own meals and favorite beverages to enjoy as you glide through pristine waters. Each windjammer is a piece of Maine's maritime history, with three of them listed on the National Register of Historic Places. Remember to dress comfortably for the weather.
Places you'll visit
Reviews
I hadn't sailed in a long time, so going out on the ship was a delightful experience. The vessel is well-maintained and ideal for enjoying the views of Portland's harbor. The crew is friendly and eager to share the boat’s history. I highly recommend this if you're considering a trip like this.
We had an amazing time on the sunset cruise. It was a bit chilly, but we were well-prepared and kept warm. The crew provided excellent information about the sights. I highly recommend this experience to anyone nearby.
This was a lovely tour, although it could have been improved had the weather been nicer, as it was gray, cloudy, and lacked wind for sailing. Nature can be unpredictable. Nevertheless, the crew was fantastic and engaging, making us feel at home by assisting with hoisting the sails. I look forward to experiencing this tour again, perhaps in the spring.
The crew was excellent. Despite the strong winds, they took the time to explain the sailing process thoroughly and what we could expect.
An outstanding experience - the captain was fantastic! He had extensive knowledge and shared wonderful stories. I highly recommend this for anyone wanting to explore the Portland coastline.
The sunset views were stunning and I had a great time. I got to assist in lifting the main sail, and the crew was open to questions. There aren't any traditional seats; you sit on the top deck for an unobstructed view of the water. You can bring your own food and drinks, but be cautious on windy days, as the boat can lean a lot and the waves can rock it significantly. This experience may not be ideal for those prone to motion sickness. I really appreciated being on a genuine sailboat that is over 100 years old.
This was the most enjoyable sailing experience I've ever had. The crew was fantastic, and the atmosphere was incredibly relaxing. Time flew by; we wished it could have lasted longer. The price was excellent, especially considering the stunning views.
I arranged the sunset schooner cruise for October 26, 2025, and it was fantastic. The sunset was stunning, the wind conditions ideal, the skipper fit for his role, and the crew highly skilled. It was one of the standout moments during our 12-day Canada-New England cruise and a perfect way to end our journey before flying home from Boston. This experience is essential for creating cherished memories.
The boat was fantastic and the crew was friendly. The autumn scenery was breathtaking. Be prepared to sit on the center of the boat since there are no proper seats. Consider bringing a seat pad. They don't offer drinks or guided tours.
The cold was unbearable during the trip. I found the lack of seating quite uncomfortable. However, the views were lovely.
Reviews are paraphrased traveller feedback sourced from Viator. Original ratings and sentiment preserved.
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