Tours/Portland/Sunset Windjammer Cruise Along the Coast of Portland Maine
Viator · group up to 45 pax

Sunset Windjammer Cruise Along the Coast of Portland Maine

4.7(164)Portland1 hour
VIATOR4.8(101)TRIPADVISOR4.7(63)

Description

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.

Tour Options

Sunset Windjammer Cruise Along the Coast of Portland Maine

Itinerary

Pass by

Enjoy the beauty of the rugged coastline, complete with lighthouses and seals, as we slip through the pristine waters of Casco Bay.

Pass by

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

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.

Highlights

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

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!

Traveller Ratings

4.7
164 reviews
5
139
4
13
3
9
2
1
1
2

Important Information

  • Infants and small children can ride in a pram or stroller
  • Public transportation options are available nearby
  • Suitable for all physical fitness levels

Reviews(164)

M
Michaeline_N
July 20, 2026
Sailing into Sunset

What a great way to see Portland from the water! The crew was friendly, personable, and knowledgeable. They answered questions with enthusiasm when asked by guests. The ride was smooth and beautiful! We enjoyed seeing Portland Head Light from the water, as well as wildlife, such as seals and porpoises that came really close to our boat as we sailed. We had a great time and highly recommend this activity!

M
Michael_E
July 17, 2026
An Excellent Adventure!

Can be very windy and cooler ever if it's hot on land, great captain Dave and great crew! Don't forget to BYOB!

S
Steve_L
July 16, 2026
Great boat and great crew to sail with

Very enjoyable ride with a skilled and knowledgeable crew. Would highly recommend sailing with them.

M
MaryAnn_P
July 15, 2026
Beautiful sunset cruise off Portland Maine

The amount of time was perfect. Lots to look at, lots to experience. The captain was knowledgeable and fun. We were racing another ship to keep things exciting for the crew as well!

H
Hallie_E
July 11, 2026
Good times

It was really nice weather and the staff was great, but the boat was a little crowded. If there were maybe 10 less people it would have been 5 stars!

K
Karla_M
July 10, 2026
Sunset sailing

It’s a full boat. Hardly any room for moving or setting up a picnic. The staff were awesome. Beautiful sailing. Only wish we had less people on board.

S
Susan_E
July 10, 2026
Beautiful. Saw some...

Beautiful. Saw some seals. Very interesting watching them work the sails going out and returning. Great crew

J
jessical998
July 6, 2026
A must do

Such a great experience! We would go again in a heartbeat. The crew were all exceptional, knowledgeable about the area and so kind. We saw a seal and were told they often see other sea life but due to the heat wave they were not seeing as many. It was so relaxing and beautiful to get out on the harbor.

J
Jan_P
July 6, 2026
Beautiful views!

Beautiful boat ride. Great experience! The views were wonderful. Enjoyed the sailing experience, great photo opportunities.

T
Timothy_R
July 5, 2026
Summer Cruse

In July is pretty darn hot. Not a whole lot of relief, even if you're out on the Bay or the ocean. So if you're doing a summer cruise, come prepared. That being said, it was a wonderful relaxing couple of hours out on the ocean. It's a great way to wind down the day.

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