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Schooner Woodwind

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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
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 222 reviews
Visitor rating
  • 182
  • 26
    Very good
  • 5
  • 1
  • 6
An Annapolis Must!

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... read more

5 of 5 bubblesReviewed 2 weeks ago
Bronxville, New York
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222 Reviews from our TripAdvisor Community

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Showing 220: English reviews
Bronxville, New York
Level Contributor
16 reviews
3 attraction reviews
common_n_attraction_reviews_1bd8 3 helpful votes
5 of 5 bubbles Reviewed 2 weeks ago

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.

Level Contributor
128 reviews
42 attraction reviews
common_n_attraction_reviews_1bd8 40 helpful votes
4 of 5 bubbles Reviewed 5 weeks ago

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.

Thank FunlovingJohn
2 reviews
1 of 5 bubbles Reviewed September 17, 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
90 reviews
19 attraction reviews
common_n_attraction_reviews_1bd8 53 helpful votes
5 of 5 bubbles Reviewed September 12, 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
18 reviews
6 attraction reviews
common_n_attraction_reviews_1bd8 11 helpful votes
5 of 5 bubbles 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
5 of 5 bubbles Reviewed August 24, 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
Level Contributor
7 reviews
3 attraction reviews
common_n_attraction_reviews_1bd8 9 helpful votes
4 of 5 bubbles Reviewed August 21, 2016 via mobile

We sailed on a Saturday from 11am-1pm. It was a very hot day, and I got the tan lines to prove it! The crew made it fun, and the fiance got to help put the sails up! They also let members steer the boat, and saw some young kids do so. The sail itself was relaxing, but there wasn't much... More 

Thank Jennifer M
Philadelphia, Pennsylvania
Level Contributor
35 reviews
9 attraction reviews
common_n_attraction_reviews_1bd8 7 helpful votes
4 of 5 bubbles Reviewed August 19, 2016 via mobile

Our company held a conference in the area and chose Schooner for a dinner cruise. It was a lovely sail boat, and the crew was very accommodating. Food and drinks were also very good. Only problem was that once you get out into the open water there really isn't a way to walk around safely without feeling like you might... More 

Thank Rjon316
Norristown, Pennsylvania
Level Contributor
39 reviews
12 attraction reviews
common_n_attraction_reviews_1bd8 23 helpful votes
5 of 5 bubbles Reviewed August 18, 2016 via mobile

It was our third trip on the boat from the Wedding Crashers movie, again it was thrilling with lots of wind on the way out, we lost the wind about halfway back, it instantly became too hot, the captain would not turn the engine on until we where almost back, that was the only drawback! We can't wait until our... More 

Thank Eightbootsies
Level Contributor
11 reviews
3 attraction reviews
common_n_attraction_reviews_1bd8 1 helpful vote
5 of 5 bubbles Reviewed August 17, 2016 via mobile

Absolutely loved sailing on the Woodwind!! It was so fun and relaxing! We got to do a beer tasting while on board the night I went. The views were amazing. The staff did an excellent job. Taking my family there in a couple weeks too!! Tip: don't sit by the wheel ... Sit on the front right of the boat... More 

Thank Erica P

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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?