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Dorchester Center, MA 02124

Experience Portland's coast from Casco Bay aboard a historic Maine-built windjammer on this 2-hour tall ship cruise for $101.62 per person, with flexible snacks and drinks.
The Portland Tall Ship Cruise on Casco Bay offers an authentic maritime adventure right from Portland, USA. Priced at $101.62 per person for an approximately 2-hour voyage, this tour is a wonderful way to see the Maine coast from a unique perspective. The tour departs from the Maine State Pier and features Maine-built windjammers that are listed on the National Register of Historic Places, including the 1924-built Bagheera which can comfortably host up to 35 guests. With an average booking window of 45 days in advance, this experience attracts a steady number of water lovers seeking scenic views, seals, and a taste of maritime history.
Open to all ages, the tour stands out for its relaxed pace and flexible approach—guests are encouraged to bring their own snacks, drinks, and alcoholic beverages to enjoy during the cruise. This makes it a perfect outing for families, friends, or anyone looking for a tranquil escape on the water. While the 2-hour duration allows ample time to take in sights like lighthouses, seabirds, and the rugged coastline, it’s worth noting that the trip can be most enjoyed in good weather, as cancellations due to poor conditions are fully refundable.


This tall ship cruise offers a refreshing angle on Portland and Casco Bay that most land-based sightseeing misses. Once aboard, the focus shifts to the sea breezes and scenic horizons, with the crew providing insight into maritime life and local landmarks. The historic Maine-built schooners stand as a testament to the region’s shipbuilding legacy, adding a layer of authenticity to the experience.
The relaxed schedule means you aren’t rushed, so you can unwind while passing by lighthouses, seals, and observing seabirds in their natural habitat. The guide navigates smoothly, especially during calmer waters, providing points of view that highlight Portland’s rugged coastline and the beauty of Casco Bay.
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Every vessel used in this cruise is a wooden schooner with deep roots in Maine history. The Bagheera, built in 1924, is a highlight of the fleet, offering a sense of sailing heritage that adds to the tour’s appeal. These ships are certified by the U.S. Coast Guard and are home to life jackets for both adults and children, ensuring safety alongside tradition.
Guests can opt to actively participate by hoisting sails or steering the ship—a feature especially praised by those who want a bit of hands-on sailing experience. This participation is simply arranged by informing the crew beforehand, making it a flexible activity for those curious about maritime skills.

Starting at the Maine State Pier, the tour involves boarding a historic windjammer where guests find a comfortable seat or participate in sailing activities. During the cruise, the crew is known for being knowledgeable and friendly, eager to share stories about the vessel and the scenic sites. The lack of a narrated tour means the focus remains on visual enjoyment and interactive sailing, which many find refreshing.
Guests are encouraged to bring their own food and drinks—wine, beer, or snacks—to make the trip more personalized. The two hours pass quickly as the sail glides through the cool waters of Casco Bay, with plenty of opportunities for photo stops and seal sightings.

The meeting point is at Maine State Pier, which is accessible via public transportation, making logistics straightforward. The tour keeps the group size to a maximum of 45 travelers, maintaining an intimate atmosphere. This smaller group size enhances the personalized experience and allows for more interaction with the crew.

Reviews highlight the friendly and professional nature of the crew, with many praising their knowledge, storytelling, and willingness to engage with guests. The captain and crew are experienced in handling the vessel under varying conditions, with some reviews noting exhilarating moments such as heeling, where the boat leans sharply into the wind, providing a thrilling ride.

Because food and drinks are not included, guests should plan to bring their own snacks and beverages, including alcohol if desired. Comfortable clothing and jackets are recommended, especially since the sails can sometimes generate wind-chill. The seating on the wooden cabin roof adds to the charm but might be less comfortable on colder days, so packing a jacket or blanket is advisable.

The tour boasts an overall 4.6-star rating based on 225 reviews, with many travelers describing it as a peaceful, scenic, and fun experience. The professional crew, beautiful scenery, and authentic vessels receive high praise. Some reviewers mention overcrowding and lack of amenities for purchase as minor drawbacks, but these do not generally detract from the overall positive impression.
A few reviews note the importance of correct parking information, highlighting the need for guests to verify parking costs and options in advance. Others point out that the cruise itself is excellently handled with smooth sailing and a relaxed pace perfect for a family outing or romantic escape.

Booking typically requires around 45 days in advance, and the tour offers full free cancellation up to 24 hours before departure. The tour operates in good weather, with full refunds if canceled due to poor conditions. Because it’s a short and flexible experience, it suits those with limited time but a desire for a quality maritime adventure.
This tour provides a genuine sailing experience aboard historic Maine schooners, pairing scenic views with a relaxed, interactive voyage. The friendly crew and authentic vessels foster a sense of connection to Maine’s nautical traditions. Bringing your own food and drinks allows for a personalized outing, whether as a family activity, romantic date, or solo escape.
While it’s best enjoyed in good weather, the easy logistics and small group size make this cruise accessible and intimate. The overall high ratings reflect the experience’s quality, making it a top choice for those interested in sea views, seals, and Maine maritime history.
“Fun experience! The history of the boat was really cool, the bay was pretty, and the staff were knowledgeable and friendly.”
How long is the Portland Tall Ship Cruise?
The cruise lasts approximately 2 hours, providing ample time to enjoy the scenery and participate in sailing activities.
Can I bring my own food and drinks?
Yes, guests are encouraged to bring their own snacks, beverages, and alcohol to enjoy during the cruise.
Where does the tour start?
The tour departs from Maine State Pier in Portland.
Is the tour suitable for children?
Absolutely, this family-friendly trip is suitable for kids and adults, with options for participation in sailing.
What is the vessel like?
You’ll sail aboard a Maine-built wooden schooner listed on the National Register of Historic Places. The vessels are certified and equipped with life jackets.
What is the cancellation policy?
You can cancel free of charge up to 24 hours before the scheduled departure. Cancellations within 24 hours are non-refundable.