
Portland Tall Ship Cruise on Casco Bay
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September 2026
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Who is going?
Adults
Age 13 and over
Children
Age 12 and under
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Free cancellation up to 24 hours before. Same price on Viator, Outty earns a commission.
Traveler rating
4.6/5
Based on 242 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.
Quick answer
Is Portland Tall Ship Cruise on Casco Bay worth booking?
Portland Tall Ship Cruise on Casco Bay is a 2-hour experience in Portland, United States, from $102 per person. It scores 69 out of 100 on the Outty Ranking, which we label “Solid Choice”, based on a 4.6/5 rating across 242 reviews. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.
- Outty Ranking
- 69 / 100
- Rating
- 4.6/5 (242)
- Duration
- 2 hours
- From
- $102 per person
What better way to see the delights of Portland than from the sea in one of the famous schooner tall ships. Join us for this mid morning cruise that will make your visit to Portland live long in the memory.
What you get
About this experience
What better way to see the delights of Portland than from the sea in one of the famous schooner tall ships. Join us for this mid morning cruise that will make your visit to Portland live long in the memory.
What's included
Included
- Schooners are equipped with life jackets for adults and children
- 2 Hour Cruise
Not included
- Food and Drink
What you'll see and do
Portland
Sail aboard Bagheera, Wendameen, or Timberwind for a two-hour cruise from Portland, Maine on Casco Bay. Sailing on our windjammers is the perfect way to experience the beauty of the Maine coast, complete with lighthouses, seals, seabirds and the rugged coastline
Pass by without stopping
Casco Bay
Pack a meal, bring your favorite wine or beer and sit back and relax as you slip through the cool waters of Maine. Or, if you feel inspired, join the crew to hoist the sails or take a turn at the ship's wheel. All ages are welcome! Whether you're nine years old or 99, sailing aboard our Maine schooners is a unique adventure. All of our wooden windjammers are listed on the National Register of Historic Places and were built in Maine. Certified by the U.S. Coast Guard, Bagheera was built in 1924 and can comfortably accommodate 35 guests.
Pass by without stopping
Where it starts and ends
Meeting point
Portland
Come to the dockhouse at 56 Commercial Street and give your name.
Hotel pickup
No pickup: everyone meets at the start point.
Ends at
Come to the dockhouse at 56 Commercial Street and give your name.
Options you can book
Portland Tall Ship Cruise on Casco Bay
Private Cruise- up to 6 People
Before you book
- Cancellation
- For a full refund, cancel at least 24 hours before the scheduled departure time.
- Languages
- en
- Ticket
- Mobile Only
- Runs on
- Every day
- Group size
- Up to 15 travelers per booking
- Operated by
- Wow A Tour
Know before you go
- Public transportation options are available nearby
- Suitable for all physical fitness levels
Photos






What travelers are saying
Outty’s summary of the themes that recur across 242 traveler reviews. Written by us, not quoted from reviewers.
Knowledge and storytelling
2 mentionsReviewers describe the commentary as informative rather than scripted.
Organization
2 mentionsPickup, timing, and logistics are described as running smoothly.
Traveler reviews
242 verified traveler reviews for Portland Tall Ship Cruise on Casco Bay. Ratings and reviews provided by Viator and Tripadvisor.
Lovely couples activity
Great sail and a friendly crew who were very knowledgeable and answered all of our questions!
via Tripadvisor
Welcome to Portland
On time departure, welcoming crew. Not much wind, but clearly not their fault - but a risk with sailing. Saw seals and porpoise. Lovely introduction to Portland on our first full day there.
via Tripadvisor
Very peaceful boat ride...
Very peaceful boat ride with beautiful views. The crew, boarding ticket staff was great. I had missed my early boat ride ( running late ) they worked with me to find another boat ride later the same day
via Viator
So much fun!
We started out in the morning with little breeze, but the crew was fabulous and we motored out and found the wind. As predicted, the winds picked up as mid-day approached and we had a great sail!
via Viator
The trip was amazing! We...
The trip was amazing! We were on the smaller of the 2 boats and had a great time! The crew was great! We were mostly interested in seeing lighthouses and this trip did not disappoint. We booked this through Viator, and that was a mistake. Their custom service is terrible. We kept trying to get out tickets online and couldn't. We had to download the app, then received a link in an email, which pretty much took us back to same page that showed that this is not the ticket, that we need to download the app to get the tickets. We went round and round on this for days. Finally on the morning of the cruise, about 2 hours before we were scheduled to sail, we called Viator customer support. We spent a lot of time on the phone and were told that they couldn't contact anyone with the ship company because they wouldn't be open for a couple more hours since they were on the west coast. Our trip is in Portland Maine on the east coast. This woman didn't have it together. Much like trying to get the tickets, this just kept going round and round. We finally just went to the location and asked if we were on the list, and we were, but the boat was sailing from a different dock. The cruise company tried to contact all the passengers, but we were never notified of the change. Luckily we had time to walk to the other dock and made it on the ship in plenty of time. The trip was amazing, Viator, not so much.
via Viator
Good to know
- Duration
- 2 hours
- Free cancellation
- Up to 24h before
- Minimum age to book
- All ages
- Availability
- Bookable today
- Runs on
- Every day
- Price range
- $102 to $785
- Hotel pickup
- No pickup, meet at start point
- Booked in 30 days
- 85
- Verdict
- Solid Choice
Why this scores 69
The Outty Ranking is a weighted composite. Here is how this experience performed on each component.
Portland Tall Ship Cruise on Casco Bay: questions travelers ask
Practical detail on this experience, plus the wider planning questions for Portland.
How much does Portland Tall Ship Cruise on Casco Bay cost?
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Prices start at $102 per person. The final price depends on the date, the time slot and the number of travelers, and peak weekends in Portland usually price higher than midweek mornings. Live pricing and remaining availability are confirmed on the booking screen before you pay.
How long does Portland Tall Ship Cruise on Casco Bay take?
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Plan for about 2 hours from start to finish, not counting travel to the meeting point. Most travelers leave another 30 minutes on either side so the rest of the day in Portland is not rushed.
Is Portland Tall Ship Cruise on Casco Bay worth it?
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It holds an Outty Ranking of 69 out of 100, which we label "Solid Choice". That score blends traveler sentiment (4.6/5 across 242 reviews), the depth of that review evidence, recent booking momentum, value for money against comparable last minute in Portland, and how flexible the cancellation terms are.
Can I cancel or reschedule Portland Tall Ship Cruise on Casco Bay?
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Yes. Cancel free up to 24 hours before the start time for a full refund. Inside that window the booking is non-refundable, and no-shows are not refunded.
Is Portland Tall Ship Cruise on Casco Bay suitable for kids and families?
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Yes, all ages are welcome. Families should still weigh the 2-hour running time, and strollers are easier on the earlier, quieter departures.
How far in advance should I book Portland Tall Ship Cruise on Casco Bay?
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Around 85 people booked this in the last 30 days, so popular slots go early. Two to three weeks ahead is comfortable in shoulder season, while summer weekends and holidays in Portland can sell out a month out. Same-day spots do open up when other travelers cancel, so it is worth checking if you are already in town.
What should I bring or wear?
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Bring photo ID, your booking confirmation on your phone, a refillable water bottle and comfortable shoes. Dress for the weather in Portland and add a light layer if any part of the 2-hour experience runs outdoors or after sunset.
Where does Portland Tall Ship Cruise on Casco Bay start and how do I get there?
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The exact meeting point and directions are on your voucher once you book, and they sit in central Portland within reach of public transport. Arrive 15 minutes early: late arrivals are treated as no-shows by most operators.
What are the best things to do in Portland?
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Portland sells lighthouse and lobster-boat tours in Casco Bay, Old Port food and brewery walks, seal and puffin cruises, and fall foliage runs up the Maine coast. On Outty we rank every Portland experience on the same 0 to 100 scale, and alongside this one the highest scorers right now include The Real Portland Tour: City and 3 Lighthouses Historical Tour with a Real Local, Portland, Maine: Hidden Histories Guided Walking Tour, A Walk Through Time Tour in Portland. The city page groups everything into most popular, highest reviewed, last minute and family-friendly so you can build a day around what actually delivers.
When is the best time to visit Portland?
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June to October, with peak foliage in early October. Booking patterns follow the same curve: prices and queues climb in peak weeks, while shoulder season gives you better availability on the top-ranked experiences and more room to change plans.
How many days do you need in Portland?
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Three full days covers the headline sights without sprinting. A workable rhythm is one anchor experience each morning, such as this one, an unhurried afternoon in a single neighborhood, then a food or nightlife booking in the evening. Five days lets you add a day trip outside the city.
Do I book through Outty or through the operator?
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Outty ranks and explains the experiences, then hands you to Viator to complete the booking with the operator directly. The price is the same as booking on Viator yourself, and Outty earns an affiliate commission on the referral, which is how the rankings stay free to read.
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