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

Afternoon Windjammer Cruise Along the Coast of Portland Maine

4.6(214)Portland1 hour
VIATOR4.6(127)TRIPADVISOR4.7(87)

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). 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.

Tour Options

Afternoon Windjammer Cruise Along the Coast of Portland Maine
  • Duration: 2 hours

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.

Highlights

Life jackets

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!

Traveller Ratings

4.6
214 reviews
5
167
4
30
3
10
2
3
1
4

Important Information

  • 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

Reviews(214)

D
Dave M
July 20, 2026
A great sailing experience

Captain James and crew gave us a wonderful sailing experience on Casco Bay. When the sails are full and you glide across the water it is pure joy. We highly recommend.

E
Edison_M
July 19, 2026
Great afternoon activity

Great staff members, on time, very polite. Knowledgeable., easy access. Boat was very cleaned, well maintained.

T
Tour45513109897
July 19, 2026
Sailing in Casco Bay Maine

Is an excellent experience. As a family, we love sailing, and it was a pleasant, but on guide of leisurely tour. As it was a sailboat,so one is dependent on the wind. The wind was fair, but everybody worked to make it really a pleasant trip the crew the crew is pleasant and helpful. They were available to answer questions. It was a very good value!

B
Besiana_J
July 19, 2026
Amazing

unforgettable⭐⭐⭐⭐⭐ Absolutely amazing boat tour! The crew was outstanding—friendly, professional, and genuinely caring. They went above and beyond to make sure everyone was comfortable, safe, and having a great time. Their positive attitude and attention to every guest made the experience unforgettable. I highly recommend this tour to anyone looking for a memorable day on the water. Thank you for such a wonderful experience!

M
Michelle_O
July 18, 2026
Relaxing and scenic views of Portland Harbor

The guides were great. They were young brothers who knew a lot about sailing and the area. They were friendly and knowledgeable.

M
michaelyZ4438QM
July 18, 2026
Great time!

Great time! 2 hour ride, even saw porpoises. The staff were wonderful. It’s not a guided tour but you can ask questions. I enjoyed being able to sit and enjoy the trip. Definitely recommend.

L
lisadB3364LF
July 15, 2026
Thumbs Up

We had a lovely afternoon cruise. Our captain, Jonathan, was very informative and we learned a lot about windjammers. He was happy to answer all of our questions, as this was our first time on a windjammer. Would definitely book this cruise again.

E
Eric_T
July 14, 2026
We had a wonderful time. ...

We had a wonderful time. The crew was very nice and would answer any questions. The views were fantastic!

S
sammy1232018
July 12, 2026
A perfect evening

It was the perfect day for our sunset cruise. We were seated and left on time…the deck hands were lovely and if you were looking for a bit of activity one was encourage do help lifting the sails. My daughter purchased this as a birthday present for me while we were in Maine. I am so glad she did. The weather was perfect, as was the company! I’m looking for to trying another cruise with this company. Ooo you can bring snacks. Drinks of choice on board. No smoking though!!

R
Rochelle_R
July 11, 2026
Come sail away 🎵

My husband and I absolutely LOVED this adventure! It was such a great experience and was nice to get out on the ocean, with the cool breeze and sound of the ocean. The waters were calm, which made for a very smooth ride. The captain and his deck hands were amazing and had really good conversations with all of us; they were also great sports and took photos of us, when asked. We will definitely do it again, except next time, we'll take some wine and snacks!! 🍷🧀🥂🍪

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