
Afternoon Windjammer Cruise Along the Coast of Portland Maine
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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
4.7/5
Based on 262 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.
Quick answer
Is Afternoon Windjammer Cruise Along the Coast of Portland Maine worth booking?
Afternoon Windjammer Cruise Along the Coast of Portland Maine is a 2-hour experience in Portland, United States, from $69 per person. It scores 77 out of 100 on the Outty Ranking, which we label “Strongly Recommended”, based on a 4.7/5 rating across 262 reviews. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.
- Outty Ranking
- 77 / 100
- Rating
- 4.7/5 (262)
- Duration
- 2 hours
- From
- $69 per person
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 narrat
What you get
About this experience
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.
What's included
Included
- Life jackets
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!
What you'll see and do
Casco Bay
Enjoy the beauty of the rugged coastline, complete with lighthouses and seals, as we slip through the pristine waters of Casco Bay.
Pass by without stopping
Where it starts and ends
Meeting point
Portland
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.
Hotel pickup
No pickup: everyone meets at the start point.
Ends at
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.
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
- Portland Schooner Co.
Know before you go
- 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
Photos






What travelers are saying
Outty’s summary of the themes that recur across 257 traveler reviews. Written by us, not quoted from reviewers.
Knowledge and storytelling
3 mentionsReviewers describe the commentary as informative rather than scripted.
The guide
2 mentionsTravelers single out the guide as the reason the experience works.
Traveler reviews
257 verified traveler reviews for Afternoon Windjammer Cruise Along the Coast of Portland Maine. Ratings and reviews provided by Viator and Tripadvisor.
Fabulous Tour of Portland Harbor
It is the best tour on the water in Portland! Gorgeous boat, skilled and friendly crew, beauty all around. You really see the harbor, all the way out to Portland Headlight! It is so peaceful and beautiful, seeing nature and homes and the islands close up. Suggestion: if you want more of a learning experience ( rather than a peaceful, quieter experience), sit near the captain in the stern. He very generously answers questions. But without a microphone, only those around him hear what he says. Also, the 3 crew members also answer questions. We really enjoyed just observing and experiencing the peace of being on the water.
via Viator
Sunset Sailing Review
Overall, this was a nice experience and really enjoyed being out on the water and taking in the views of Casco Bay. Our original booking was the Sunset Lighthouse Cruise which was canceled without an explanation so not sure what happen, however the company tried calling me several times throughout the day and thankfully finally received the call around 3–4 PM, only a few hours before our scheduled 6:30 PM cruise, so thankfully was still able to make it! Once getting on the boat, the views were beautiful, and it was relaxing to be out on the water. However, we did ended up seeing one lighthouse and few seal encounters but didn’t get to explore as much of the bay as I had expected. We also left the shore a bit little later than the other sail boat and returned approximately few minutes earlier than expected. There were also some sailing difficulties along the way that seemed to delay us but glad the crew gpt it figured out. I’m glad we went and did enjoy the experience, but I wish we had been able to see more of Casco Bay. I would recommend it for the views and the experience of being out on the water with company. Hoping to visit again and hopefully get to experience the Sunset Lighthouse Cruise!!
via Tripadvisor
Schooner
Clean boat friendly staff Relaxing cruise Although nothing was said from the captain or the two other sailors, it was enjoyable. Wish they would’ve provided some history or other facts about the schooner or Portland. He did say he was not going to talk. And he did not!
via Viator
Casco Bay's hundreds of...
Casco Bay's hundreds of rock islands are awesome and seeing many of them on such a beautiful old ship was special.
via Viator
Beautiful afternoon sail
Wonderful afternoon sail on the bay on an authentic old sail boat. There is no set tour route due to changing wind and sea conditions. As such there is no narrated guide to places and things along the way. The crew will however answer questions about whatever you ask and are very knowledgeable between hoisting and adjusting sails. There are no drinks or snacks so bring your own if you want any of that. Overall a great way to see Portland from the sea and we'll worth the price.
via Tripadvisor
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
- Hotel pickup
- No pickup, meet at start point
- Booked in 30 days
- 92
- Verdict
- Strongly Recommended
Why this scores 77
The Outty Ranking is a weighted composite. Here is how this experience performed on each component.
Afternoon Windjammer Cruise Along the Coast of Portland Maine: questions travelers ask
Practical detail on this experience, plus the wider planning questions for Portland.
How much does Afternoon Windjammer Cruise Along the Coast of Portland Maine cost?
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Prices start at $69 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 Afternoon Windjammer Cruise Along the Coast of Portland Maine 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 Afternoon Windjammer Cruise Along the Coast of Portland Maine worth it?
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It holds an Outty Ranking of 77 out of 100, which we label "Strongly Recommended". That score blends traveler sentiment (4.7/5 across 262 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 Afternoon Windjammer Cruise Along the Coast of Portland Maine?
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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 Afternoon Windjammer Cruise Along the Coast of Portland Maine 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 Afternoon Windjammer Cruise Along the Coast of Portland Maine?
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Around 92 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 Afternoon Windjammer Cruise Along the Coast of Portland Maine 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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