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Schooner Woodwind

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Address: 80 Compromise Street, Annapolis Marriott Waterfront Hotel, Annapolis, MD 21401
Phone Number: +1 410-263-7837
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10:00 am - 6:30 pm
Closed now
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Sun - Sat 10:00 am - 6:30 pm

The classic, wooden 74' Schooner Woodwind sails multiple cruises daily (in...

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!

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TripAdvisor Reviewer Highlights

Read all 193 reviews
Visitor rating
  • 163
  • 20
    Very good
  • 4
  • 1
  • 5
Best sail of my 66 years!

How thrilling to go out on this beautiful sailboat and trust the Captain & crew (and the wind) to provide you with a 'gold medal memory.' We go out at least once a month and take... read more

5 of 5 starsReviewed yesterday
Annapolis, Maryland
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193 Reviews from our TripAdvisor Community

Date | Rating
  • English first
  • Portuguese first
  • Any
English first
Annapolis, Maryland
Level Contributor
10 reviews
5 attraction reviews
common_n_attraction_reviews_1bd8 4 helpful votes
5 of 5 stars Reviewed yesterday NEW

How thrilling to go out on this beautiful sailboat and trust the Captain & crew (and the wind) to provide you with a 'gold medal memory.' We go out at least once a month and take all out-of-town guests on this sail. It is exhilarating!

Thank Miscue2013
Level Contributor
6 reviews
5 of 5 stars Reviewed December 16, 2015

We live in Annapolis, yet the Schooner is something we do each year, with visiting guests or a date!

Thank Robin D
Level Contributor
197 reviews
51 attraction reviews
common_n_attraction_reviews_1bd8 85 helpful votes
5 of 5 stars Reviewed November 12, 2015

Took a late afternoon trip with one daughter and four grand-children. It was perfect condition for sailing on the Chesapeake Bay; warm sunny day and a nice wind. Almost went under the Bridge. One grand-children helped with sails and another one steering. We all enjoyed the complimentary soft drink and snack. The crew were very friendly and answered our questions.... More 

Thank PAC168
Washington DC, District of Columbia
Level Contributor
5 reviews
4 attraction reviews
common_n_attraction_reviews_1bd8 5 helpful votes
1 of 5 stars Reviewed October 29, 2015

I really enjoyed sailing on the Woodwind before my latest experience. I bought a ticket for the October Lighthouse Cruise. This would have been my eight cruise on the Woodwind and my third Lighthouse Cruise. Unfortunately three week before the cruise I was rushed to the hospital after having a seizure and was left temporarily unable to walk on my... More 

Thank Dean C
Bill M, Manager at Schooner Woodwind, responded to this review

I have since talked to Dean C. to deal with this complaint directly. We have given him a chance to sail with us again, and he was pleased with the invitation. More 

Level Contributor
44 reviews
6 attraction reviews
common_n_attraction_reviews_1bd8 26 helpful votes
5 of 5 stars Reviewed October 28, 2015

Had a beautiful sunny 70 degree day for this sail. Captain was very knowledgeable about the area and informative on the cruise. The two crew members were both very friendly and struck up conversations with many passengers. Offered a free water or soda and snack during the cruise and beer and wine available for purchase. Had the passengers who wanted... More 

Thank ocean_lovin_mom
Annapolis, Maryland
Level Contributor
132 reviews
73 attraction reviews
common_n_attraction_reviews_1bd8 73 helpful votes
5 of 5 stars Reviewed October 21, 2015

There are two Woodwind Schooners and they are identical Great Lake schooners that offer an incredible ride. They leave off the dock on the backside of the Marriott Hotel. The owners and crew offer the best way to get out on the water in Annapolis. Depending on the wind, you will either sail up the Severn River, or out into... More 

Thank Steve C
Queenstown, Maryland
Level Contributor
206 reviews
45 attraction reviews
common_n_attraction_reviews_1bd8 49 helpful votes
5 of 5 stars Reviewed October 3, 2015

Four of us went out on a windy and cloudy day. The conditions were ideal for an outstanding cruise on the Chesapeake Bay. The captain and the crew were entertaining and told us about the area and bout themselves making the trip even more fun. A good wind made for some exciting sailing. The ship is a beautiful wonderful experience.... More 

Thank Denver7889
Sumter, South Carolina
Level Contributor
20 reviews
14 attraction reviews
common_n_attraction_reviews_1bd8 1 helpful vote
4 of 5 stars Reviewed October 1, 2015

Recently took afternoon sailing trip on Schooner Woodwind and both the trip and crew were delightful.

Thank tneill2015
Arlington, Virginia
Level Contributor
73 reviews
15 attraction reviews
common_n_attraction_reviews_1bd8 33 helpful votes
5 of 5 stars Reviewed September 26, 2015

If you have ever moved across the water with only the wind as your energy source you will love this cruise. If, like me, you have never had this experience, you are in for a real treat. The captain uses her engine just for leaving and approaching the dock, and the rest of the time she, her crew and her... More 

Thank Brotherdickdca1981
Essex, New York
Level Contributor
20 reviews
common_n_attraction_reviews_1bd8 32 helpful votes
5 of 5 stars Reviewed September 23, 2015 via mobile

The staff was great, the boat was great, the ride was fun and the scenery wonderful. Can't wait to go back! You see the Naval Academy, the Bay Bridge and the beautiful Chesapeake Bay.

Thank KScottieG

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Questions & Answers

Here's what previous visitors have asked, with answers from representatives of Schooner Woodwind and other visitors
2 questions
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Plymouth, Minnesota

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Questions? Get answers from Schooner Woodwind staff and past visitors.
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Typical questions asked:
  • Will you pick up and drop off at my hotel?
  • I have a family of 7. Can your tour accommodate all of us together?
  • How should I dress for this tour?