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

Sunset Windjammer Cruise Along the Coast of Portland Maine

Outty Ranking 75 4.7 · 218 traveler reviews2 hoursFrom $77
Instant mobile ticketSpots available today

Outty Ranking

75/100

Strongly Recommended. Our proprietary evaluation. How we score

Traveler rating

4.7/5

Based on 218 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.

Quick answer

Is Sunset Windjammer Cruise Along the Coast of Portland Maine worth booking?

Sunset Windjammer Cruise Along the Coast of Portland Maine is a 2-hour experience in Portland, United States, from $77 per person. It scores 75 out of 100 on the Outty Ranking, which we label “Strongly Recommended”, based on a 4.7/5 rating across 218 reviews. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.

Outty Ranking
75 / 100
Rating
4.7/5 (218)
Duration
2 hours
From
$77 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). All ages are welcome, whether you are nine years old or 99, sailing aboard one of our Maine historic schooners is a unique adventure. 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 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). All ages are welcome, whether you are nine years old or 99, sailing aboard one of our Maine historic schooners is a unique adventure. 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 of our wooden windjammers were built in Maine and three are listed on the National Register of Historic Places.

    What's included

    Included

    • Environmentally friendly marine composting toilet
    • Life jackets for adults and children
    • 2 Hour Cruise

    Not included

    • Food and drink—But feel free to bring your own!
    • Gratuities
    • 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

    2. See the gorgeous skyline of Portland, Maine's largest city which was established in 1786. Observe Portland's working waterfront as fishing boats depart and return to the wharves that form the heart of Portland and are home to local businesses that have been passed down for generations.

      Pass by without stopping

    3. Fort Gorges

      Notice the massive granite blocks that form the iconic military fort, Fort Gorges, which was built from 1858 to 1864. These striking stone blocks that are now interwoven with nature are quite beautiful to witness.

      Pass by without stopping

    Where it starts and ends

    Meeting point

    Portland

    Please check your reservation to see the meeting point for your cruise. 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. 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.
    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
    • Suitable for all physical fitness levels

    Photos

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

    What travelers are saying

    Outty’s summary of the themes that recur across 216 traveler reviews. Written by us, not quoted from reviewers.

    Photo opportunities

    3 mentions

    The views and photo stops come up again and again.

    Traveler reviews

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

    5 star
    181
    4 star
    16
    3 star
    14
    2 star
    2
    1 star
    3
    Sort
    779abigailz · October 2026

    Excellent Time!

    The crew was so knowledgeable and nice. We enjoyed every second!

    via Tripadvisor

    Jessica_D · October 2026

    Book this sunset cruise!

    This was the best sunset cruise! The crew was so friendly. They offered an opportunity to help hoist the sails for those that wanted a full sailing experience. We had ample space. There’s a bathroom on board and you could bring your own beverage and snacks. Views were amazing in October.

    via Viator

    Maria_P · October 2026

    Loved it!

    I recommend this to everyone, its a great way to experience a bit of Portland. It was relaxing and beautiful.

    via Viator

    Susan_F · October 2026

    Windjammer Cruise

    Traveling in a windjammer is fun, but we would have enjoyed it more had our captain gave us more information about what we are seeing on the water and along the coastline. He only spoke when we asked questions. The ride couldhave been more fun is he had a narrative.

    via Viator

    ELIZABETH_B · October 2026

    Perfect Evening with Great Views

    The staff were great, particularly Tyler and Mya. The evening was beautiful. We lucked out with the weather and the sunset was incredible. We traveled early October.

    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
    76
    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 75

    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)75
    Booking momentum (14% weight)70
    Value for money (12% weight)67
    Listing quality (10% weight)85
    Local standing (8% weight)50
    Booking flexibility (8% weight)100

    Sunset 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 Sunset Windjammer Cruise Along the Coast of Portland Maine cost?

    +

    Prices start at $77 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 Sunset 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 Sunset Windjammer Cruise Along the Coast of Portland Maine worth it?

    +

    It holds an Outty Ranking of 75 out of 100, which we label "Strongly Recommended". That score blends traveler sentiment (4.7/5 across 218 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 Sunset 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 Sunset 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 Sunset Windjammer Cruise Along the Coast of Portland Maine?

    +

    Around 76 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 Sunset 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 Sunset Windjammer Cruise Along the Coast of Portland Maine?

    +

    Included: Environmentally friendly marine composting toilet; Life jackets for adults and children; and 2 Hour Cruise. Not included: Food and drink—But feel free to bring your own!; Gratuities; 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 Sunset Windjammer Cruise Along the Coast of Portland Maine?

    +

    Please check your reservation to see the meeting point for your cruise. 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 is not included, so plan your own transport and arrive 15 minutes early.

    Will I get instant confirmation and a mobile ticket for Sunset 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 Sunset 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. If accessibility is critical, contact the operator after booking to confirm arrangements for your date.

    What happens to Sunset 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 Sunset Windjammer Cruise Along the Coast of Portland Maine?

    +

    Across 218 reviews averaging 4.7 out of 5, recurring themes include photo opportunities. The views and photo stops come up again and again.

    Ready to lock in your spot?

    Pick a date, choose your group, and see the exact price for Sunset Windjammer Cruise Along the Coast of Portland Maine.

    Pick your date