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Schooner Woodwind

Certificate of Excellence
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Address: 80 Compromise St, Annapolis Marriott Waterfront Hotel, Annapolis, MD 21401-1810
Phone Number:
+1 410-263-7837
10:00 am - 6:30 pm
Open 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 226 reviews
Visitor rating
  • 184
  • 27
    Very good
  • 6
  • 1
  • 6
Warm sunny Sunday in Annapolis with the chance to be casually on the water

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... read more

Reviewed yesterday
Cleveland, Ohio
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226 Reviews from our TripAdvisor Community

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Showing 224: English reviews
Cleveland, Ohio
Level Contributor
8 reviews
4 attraction reviews
Reviewed yesterday NEW

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
Philadelphia, Pennsylvania
Level Contributor
17 reviews
4 attraction reviews
common_n_attraction_reviews_1bd8 5 helpful votes
Reviewed 2 days ago NEW

Decided to book a sunset sail. Tickets were bought a few days in advance.. It was a very cool and cloudy evening. The sail was delightful even though the weather was not. The crew was extremely accommodating and knowledgeable which made for a lovely evening. It must be really enjoyable when the weather is more coopertive. 😢👍⚓️

Thank cesloan2
Level Contributor
37 reviews
15 attraction reviews
common_n_attraction_reviews_1bd8 7 helpful votes
Reviewed 1 week ago via mobile

Great tour out on the water and enjoyable day. A little expensive but overall makes for a fun day out on the water in Annapolis(which is the way you need to see annapolis). Fun crew and they give you alcohol, what could be better

Thank vacaexpert777
Fairfax, Virginia
Level Contributor
307 reviews
85 attraction reviews
common_n_attraction_reviews_1bd8 98 helpful votes
Reviewed 3 weeks ago

My husband and I had been wanting to go on a sail boat for a while now, we finally found a location and price we were happy with. The only issue was that the boat didn't go far, for a 2 hour sail we stayed right outside of the docking/port area we could still see the loading docks. So this... More 

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

Hello FFXTravelers, Thank you for choosing the Schooner Woodwind for your first sailing experience. Sailing is a different experience with Mother Nature every time you step aboard. We offer a true sailing experience in the two hours that we have our guests on board. On some trips, our sailboats travel a greater distance than other trips due to wind speed.... More 

Bronxville, New York
Level Contributor
16 reviews
3 attraction reviews
common_n_attraction_reviews_1bd8 4 helpful votes
Reviewed October 8, 2016

I've done this twice now in my two visits to Annapolis. Enjoyed a beautiful sunset sail both times. In July, the boat was full, but everyone had a place to sit. In October, there was plenty of room to move about, if that's your thing. Complimentary water or soda and a snack. Beers, wines, and champagne also available.

1 Thank EPBOL
Level Contributor
151 reviews
48 attraction reviews
common_n_attraction_reviews_1bd8 43 helpful votes
Reviewed September 18, 2016

Beautiful afternoon trip on one of two tall masted schooners. The crew were very fun and professional. They took us out on the bay for about an hour and a half. Very family friendly event. Beautiful views of Annapolis harbor and the bay.

1 Thank FunlovingJohn
2 reviews
Reviewed September 18, 2016 via mobile

As stated in other reviews the boats are overcrowded, to the point they feel unsafe at times. If you are near the end of the line you will get stuck in the middle of the boat, below the advertising tarp, with no breeze. The captain and crew do not seem to care that everyone has an enjoyable experience. Hated every... More 

Thank John P
BethLeath, Manager at Schooner Woodwind, responded to this review

I am so sorry to hear that you hated the cruise. I looked at the comment cards that were handed back to us by over 90% of the guests on the boat and cruise you were on. No one else had the same experience as you. In fact, people wrote glowing remarks. Like, "This is our second cruise and we... More 

Kent, UK
Level Contributor
113 reviews
27 attraction reviews
common_n_attraction_reviews_1bd8 62 helpful votes
Reviewed September 13, 2016

We took the 5.30pm Sun Set tour on Woodwind. There was little wind but we still had a look into creeks and secret places around Chesapeake Bay near Annapolis. As the sun went down we returned to Annapolis to get beautiful pictures. Interesting history from all the crew, a few people had a go pulling ropes. It was a relaxing... More 

Thank hanskraay
Level Contributor
17 reviews
6 attraction reviews
common_n_attraction_reviews_1bd8 6 helpful votes
Reviewed September 10, 2016

This is a super way to view the Chesapeake. Though there was no wind the captain/owner made it such a fun and interesting trip. He knows everything about sailing, people that live on the bay, history of the bay, and is super fun. His crew was very nice and helpful, they involve you in raising the sails if you like,... More 

Thank natemorrison
Chantilly, Virginia
Level Contributor
49 reviews
21 attraction reviews
common_n_attraction_reviews_1bd8 13 helpful votes
Reviewed August 25, 2016

The crew on the Schooner Woodwind is very professional and fun to sail with. Our trip was on the 1:30 PM sail for 2 hours on the Chesapeake Bay. Luckily we had good wind and the weather was perfect for a day on the water. I would definitely sail with this company again when I go back to Annapolis.

Thank 123lovetravel2013

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Questions & Answers

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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?