Afternoon Windjammer Cruise Along the Coast of Portland Maine
Portland, United States

Afternoon Windjammer Cruise Along the Coast of Portland Maine

Outty Ranking 78 4.7 · 305 traveler reviews2 hoursFrom $69
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Outty Ranking

78/100

Strongly Recommended. Our proprietary evaluation. How we score

Traveler rating

4.7/5

Based on 305 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 78 out of 100 on the Outty Ranking, which we label “Strongly Recommended”, based on a 4.7/5 rating across 305 reviews. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.

Outty Ranking
78 / 100
Rating
4.7/5 (305)
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 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 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

    1. 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 30 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

    Afternoon Windjammer Cruise Along the Coast of Portland Maine, photo 2Afternoon Windjammer Cruise Along the Coast of Portland Maine, photo 3Afternoon Windjammer Cruise Along the Coast of Portland Maine, photo 4Afternoon Windjammer Cruise Along the Coast of Portland Maine, photo 5Afternoon Windjammer Cruise Along the Coast of Portland Maine, photo 6Afternoon Windjammer Cruise Along the Coast of Portland Maine, photo 7

    What travelers are saying

    Outty’s summary of the themes that recur across 295 traveler reviews. Written by us, not quoted from reviewers.

    Photo opportunities

    2 mentions

    The views and photo stops come up again and again.

    Traveler reviews

    295 verified traveler reviews for Afternoon Windjammer Cruise Along the Coast of Portland Maine. Ratings and reviews provided by Viator and Tripadvisor.

    5 star
    234
    4 star
    38
    3 star
    14
    2 star
    5
    1 star
    4
    Sort
    Christine_H · October 2026

    Peaceful Tide

    This was a relaxing experience. The crew was friendly and helpful but not requiring our attention. This allowed us to relax and enjoy the beautiful scenery.

    via Viator

    S1435QIandreaw · October 2026

    Wonderful

    It was a lovely experience! The captain and crew were lovely and we even helped hoist the sails. Casco Bay is lovely.

    via Tripadvisor

    BaltoMan52 · October 2026

    Better Options Available

    If you are wanting to sail around Casco Bay and you have even a minimal amount of sailing experience, this is not for you. We went on a beautiful Saturday afternoon with about an 8-10 knot breeze. The crew did raise the sails, but the engine never went off, the ship never deviated from its straight line course,and the noise from the engine was annoying. This was essentially a powerboat cruise with the sails up. Also, i think they overbook. I am 74 and don't expect an easy chair on a sailboat. But there were so many people there was not any room for me to even put my butt on the deckhouse. I had to sit on the deck or stand. There is no narrative from the captain or crew (which is stated on their website). But if this is your first time in Casco Bay you will appreciate hearing about the history of and way of life around the islands. Finally, this is not a 2 hour cruise. The last 20-25 minutes was spent about 1/4 mile from the dock while the crew dropped and furled the sails. There are better options if you want to cruise around Casco Bay.

    via Tripadvisor

    254kevg · October 2026

    A Sunny 1st Afternoon Sail with a Great Captain and Crew

    My wife and I had a great experience on the Bagheera Schooner. The first afternoon sail at 12 noon was a perfect time. The captain and crew of 2 were very welcoming, personable, and love what they do. Though it is not a guided tour the crew engage with everyone throughout. Dress in layers and know that if the sails are up you may be on the shady side of the boat and it gets chilly. They had blankets to offer but try to dress accordingly. Access from the Maine State Pier is relatively easy but know you may have to navigate ferry passengers and traffic. Highly recommend the Windjammer Cruise.

    via Tripadvisor

    Mylina_E · October 2026

    Trip was wonderful. Very...

    Trip was wonderful. Very smooth sailing and the captain and crew were helpful answering questions about things

    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
    Hotel pickup
    No pickup, meet at start point
    Booked in 30 days
    107
    Verdict
    Strongly Recommended

    Who runs this experience

    Operated by Portland Schooner Co., who run 8 experiences we rank across 1 city, with an average Outty Ranking of 64.8.

    See everything Portland Schooner Co. runs

    Why this scores 78

    The Outty Ranking is a weighted composite. Here is how this experience performed on each component.

    Traveler sentiment (30% weight)79
    Review evidence (18% weight)79
    Booking momentum (14% weight)76
    Value for money (12% weight)74
    Listing quality (10% weight)85
    Local standing (8% weight)50
    Booking flexibility (8% weight)100

    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?

    +

    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?

    +

    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?

    +

    It holds an Outty Ranking of 78 out of 100, which we label "Strongly Recommended". That score blends traveler sentiment (4.7/5 across 305 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?

    +

    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?

    +

    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?

    +

    Around 107 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?

    +

    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?

    +

    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?

    +

    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?

    +

    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?

    +

    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?

    +

    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.

    What is included in Afternoon Windjammer Cruise Along the Coast of Portland Maine?

    +

    Included: Life jackets. Not included: Food and Drink—But feel free to bring your own!; and Group Narration - Our captain and crew are happy to answer questions about the harbor sigh. Always check the voucher for the final list before you travel.

    Where is the meeting point for Afternoon Windjammer Cruise Along the Coast of Portland Maine?

    +

    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. Hotel pickup is not included, so plan your own transport and arrive 15 minutes early.

    What languages is Afternoon Windjammer Cruise Along the Coast of Portland Maine offered in?

    +

    It runs in English. Pick your language when choosing a date and time, as not every departure runs in every language.

    Will I get instant confirmation and a mobile ticket for Afternoon Windjammer Cruise Along the Coast of Portland Maine?

    +

    Confirmation is sent by the operator after booking, usually within 48 hours; if it is not confirmed you are not charged. Mobile tickets are accepted, so you can show the voucher on your phone.

    Is Afternoon Windjammer Cruise Along the Coast of Portland Maine wheelchair or stroller accessible?

    +

    The operator notes: Infants and small children can ride in a pram or stroller; and Specialized infant seats are available. If accessibility is critical, contact the operator after booking to confirm arrangements for your date.

    What happens to Afternoon Windjammer Cruise Along the Coast of Portland Maine if the weather is bad?

    +

    This experience depends on good weather. If it is canceled because of poor weather, you are offered a different date or a full refund.

    What do travelers say about Afternoon Windjammer Cruise Along the Coast of Portland Maine?

    +

    Across 305 reviews averaging 4.7 out of 5, recurring themes include photo opportunities. The views and photo stops come up again and again.

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