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Schooner Woodwind

Certificate of Excellence
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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...

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 191 reviews
Visitor rating
  • 161
  • 20
    Very good
  • 4
  • 1
  • 5
Perfect day on the water

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... read more

5 of 5 starsReviewed 2 weeks ago
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191 Reviews from our TripAdvisor Community

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Date | Rating
  • English first
  • Portuguese first
  • Any
English first
Level Contributor
193 reviews
51 attraction reviews
common_n_attraction_reviews_1bd8 78 helpful votes
5 of 5 stars Reviewed 2 weeks ago

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 4 weeks ago

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
Level Contributor
44 reviews
6 attraction reviews
common_n_attraction_reviews_1bd8 25 helpful votes
5 of 5 stars Reviewed 4 weeks ago

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
21 reviews
10 attraction reviews
common_n_attraction_reviews_1bd8 6 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
184 reviews
41 attraction reviews
common_n_attraction_reviews_1bd8 48 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
15 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 32 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
19 reviews
common_n_attraction_reviews_1bd8 32 helpful votes
5 of 5 stars Reviewed September 23, 2015

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
New Hampshire
Level Contributor
277 reviews
157 attraction reviews
common_n_attraction_reviews_1bd8 144 helpful votes
5 of 5 stars Reviewed September 22, 2015

We took the sunset sail on Saturday and it was completely booked for BOTH schooners when we got there. We had purchased our tickets a few days earlier online, so all was good. We were on the Woodwind II with captain Mickey. The exciting thing about this particlar Schooner is that it was the one used in the movie "Wedding... More 

Thank tdtid
Philadelphia, Pennsylvania
Level Contributor
31 reviews
8 attraction reviews
common_n_attraction_reviews_1bd8 11 helpful votes
5 of 5 stars Reviewed September 18, 2015

Beautiful boat, great crew, wonderful afternoon sail. We took the 3pm sail and it was a beautiful day. Ken the captain was wonderful, both funny and informative. My husband was able to take the helm and other guests helped hoist the sails, fun time! They give you a water or a soft drink and a bag of chips. They also... More 

Thank AMPM78

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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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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?