We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Schooner Woodwind

Certificate of Excellence
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Get directions
Address: 80 Compromise St, Annapolis Marriott Waterfront Hotel, Annapolis, MD 21401-1810
Phone Number:
+1 410-263-7837
10:00 - 18:30
Open now
See all hours
Sun - Sat 10:00 - 18:30

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!

read more

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

Reviewed 8 October 2016
Bronxville, New York
Add Photo Write a Review

222 Reviews from our TripAdvisor Community

Traveller rating
Traveller type
Time of year
Showing 220: English reviews
Bronxville, New York
Level Contributor
16 reviews
3 attraction reviews
common_n_attraction_reviews_1bd8 4 helpful votes
Reviewed 8 October 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
146 reviews
48 attraction reviews
common_n_attraction_reviews_1bd8 43 helpful votes
Reviewed 18 September 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 18 September 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
109 reviews
25 attraction reviews
common_n_attraction_reviews_1bd8 61 helpful votes
Reviewed 13 September 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 10 September 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 25 August 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
9 reviews
3 attraction reviews
common_n_attraction_reviews_1bd8 9 helpful votes
Reviewed 22 August 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 A
Philadelphia, Pennsylvania
Level Contributor
50 reviews
15 attraction reviews
common_n_attraction_reviews_1bd8 16 helpful votes
Reviewed 19 August 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
61 reviews
16 attraction reviews
common_n_attraction_reviews_1bd8 26 helpful votes
Reviewed 18 August 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
16 reviews
4 attraction reviews
common_n_attraction_reviews_1bd8 2 helpful votes
Reviewed 18 August 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

Travellers who viewed Schooner Woodwind also viewed


Been to Schooner Woodwind? Share your experiences!

Write a Review Add Photos & Videos

Is This Your TripAdvisor Listing?

Own or manage this property? Claim your listing for free to respond to reviews, update your profile and much more.

Claim Your Listing

Questions & Answers

Here's what previous visitors have asked, with answers from representatives of Schooner Woodwind and other visitors
3 questions
Ask a question

See all questions (3)

Questions? Get answers from Schooner Woodwind staff and past visitors.
Posting guidelines
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?