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Schooner Woodwind

80 Compromise St, Annapolis Marriott Waterfront Hotel, Annapolis, MD 21401-1810
+1 410-263-7837
Review Highlights
Very Nice

Although there wasn't much wind at all on the day we went out for the 11am sail, seeing the bay by... read more

Reviewed yesterday
Kim D
Middleton, Wisconsin, United States
via mobile
Very relaxing

As a B-day present to myself and hubby, we took the sunset cruise (2 hour trip) on the Schooner... read more

Reviewed 2 days ago
Teresa B
Bloomingburg, New York
Read all 235 reviews
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The classic, wooden 74' Schooner Woodwind sails multiple cruises daily (in season) for public and private charters. Up to 48 passengers on each of our twin schooners. Whether a couple, family, party or corporate, we can accommodate you. We also have a Boat & Breakfast available (in season) on Saturdays. Come Sail Away!
  • Excellent84%
  • Very good11%
  • Average2%
  • Poor1%
  • Terrible2%
Travelers talk about
“sunset cruise” (30 reviews)
“hour sail” (14 reviews)
Closes in 23 min
All hours
Hours Today: 10:00 AM - 6:30 PM
80 Compromise St, Annapolis Marriott Waterfront Hotel, Annapolis, MD 21401-1810
+1 410-263-7837
Write a Review
Reviews (235)
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1 - 10 of 233 reviews

Reviewed yesterday via mobile

Although there wasn't much wind at all on the day we went out for the 11am sail, seeing the bay by sailboat was a treat. Much quieter and more relaxing than a motorboat tour, and the crew took great care of us with snacks and...More

Thank Kim D
Reviewed 2 days ago

As a B-day present to myself and hubby, we took the sunset cruise (2 hour trip) on the Schooner. The sun didn't cooperate but the friendliness of the crew more than made up for it. As it was Monday night, we were treated to Dave...More

Thank Teresa B
Reviewed 1 week ago

What a wonderful way to see the Bay when you don't own a sailboat. We thoroughly enjoyed our sail. The captain and crew of Woodwind were relaxed, knowledgeable of the area, and very friendly. The captain was really good about letting the kids in the...More

Thank TXGreenGal
Reviewed 2 weeks ago via mobile

This was our second trip on the woodwind. We took the 11:00 sail before it got too hot. This is a great way to sail the Chesapeake the old fashioned way. Everyone got an opportunity to steer the boat which was great. We did not...More

Thank Dave S
Reviewed July 12, 2017

It rained for about an hour before our "sunset cruise" and was still sprinkling when we boarded the Woodwind. The captain quickly got us out to better weather and a beautiful sail. We sailed all around the bay and several people were able to steer...More

Thank Shannon S
Reviewed July 4, 2017 via mobile

So enjoy this! Have been on the ship several times. A must when out of towner's visit. Have always gotten Capt. Jen- she is great. When it's windy- what a ride!!!!! Calm is nice, too. Going for the July 4, 2017 fireworks ride...I'm too excited!!!...More

Thank Paula H
Reviewed July 2, 2017 via mobile

We enjoyed a Father's day Sunday in the schooner and it was a good experience overall. It is a cool and different activity to do in Annapolis. The staff is very friendly. Our only bad experience was getting sea sick but that has nothing to...More

Thank MelimarB
Reviewed June 11, 2017 via mobile

This is my second time riding on the Schooner Woodwind. I came previously on a bachelorette party, and enjoyed myself in both settings. The crew is accommodating and informative. The views are spectacular. It's a perfect price for the experience. Highly recommend the sunset sail!...More

1  Thank Sarah I
Reviewed May 29, 2017

My wife and I recently went on Woodwind for the sunset cruise and boat and breakfast. The sunset cruise was amazing, the staff was amazing, and the view of Annapolis from the boats path was breathtaking. The boat and breakfast was hosted by Captain Jen...More

1  Thank AW0710
Reviewed May 23, 2017

Perfect chance to stay cool and see the sights without doing the work. If you are a sailor this is a kiddie ride. If you are a sightseer it is only 2 hours but packed with much fun.

Thank fclarkeiv
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Questions & Answers
Kimbercat S
June 6, 2016|
AnswerShow all 2 answers
Response from Bill M | Property representative |
Guests have the opportunity to help raise the sails, steer the schooner, and ask questions. You also can just sit back and relax! Captain may have suggestions of where best to take a lesson locally. Weight is not an issue... More
September 2, 2015|
AnswerShow all 3 answers
Response from BethLeath | Property representative |
Thank you for your question. Yes we are sailing on Labor Day from 10am-12pm, 12:30-2:30pm, 3-5pm & 5:30-7:30pm. The cost is $44/adult, $42/senior (over 60) & $27/child (under 12). Please visit our website to purchase... More
July 1, 2015|
AnswerShow all 8 answers
Response from 2118burke | Reviewed this property |
There is another nice boat out of Annapolis - it's a Priate Ship - specifically for kids. They dress up and it's great for small children. The Windwood for the evening cruise was mostly adults so not sure about daytime... More