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Schooner Woodwind

80 Compromise St, Annapolis Marriott Waterfront Hotel, Annapolis, MD 21401-1810
+1 410-263-7837
Review Highlights
Beautiful afternoon on the Bay

We took the 1230-230 cruise on a sunny autumn day. Captain and crew were friendly, experienced and... read more

Reviewed October 25, 2017
great way to experience sailing and the Chesapeake Bay

This was a great trip. I was thrilled that we were able to book so short notice. I called and... read more

Reviewed October 10, 2017
Read all 247 reviews
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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!
  • Excellent83%
  • Very good11%
  • Average2%
  • Poor1%
  • Terrible3%
Travelers talk about
“sunset cruise” (32 reviews)
“hour sail” (14 reviews)
Open Now
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Hours Today: 10:00 AM - 6:30 PM
80 Compromise St, Annapolis Marriott Waterfront Hotel, Annapolis, MD 21401-1810
+1 410-263-7837
Write a ReviewReviews (247)
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1 - 10 of 245 reviews

Reviewed October 25, 2017

We took the 1230-230 cruise on a sunny autumn day. Captain and crew were friendly, experienced and knowledgeable. About 40 guests onboard---all ages. Beverages and snacks provided.

Thank LSD11
Reviewed October 10, 2017

This was a great trip. I was thrilled that we were able to book so short notice. I called and left a voicemail around 9am. They called me back at 10am and were able to fit us in that afternoon (and during the sailboat show...More

Thank mquest
Reviewed September 26, 2017 via mobile

I am a seasoned boater and this was a first for myself and fiancé. What a wonderfully relaxing afternoon. We did the 3 pm tour and there was about 10 of us and crew was personable and knowledgeable. I got to steer the boat and...More

Thank Lisa B
Reviewed September 18, 2017

My husband and I booked a "specialty cruise" for Sunday, September 17. It was a participatory sporting for the sail boat, AND 21 other classic wooden boats. This regatta is an annual event in Annapolis, and we were fortunate that the weather [mostly] cooperated. The...More

Thank Deborah C
Reviewed September 17, 2017

This company refused to offer us a refund or even a different sail time when our son was sick and would be unable to sail the day we bought the tickets for. Only when we went to our bank to contest the charge did they...More

1  Thank ford4040
Reviewed September 10, 2017 via mobile

For nearly 20 years the Schooner Woodwind has been, literally, my happy place. Typically it's my husband and me, celebrating an anniversary and it's always amazing. But sometimes we bring small children or teenagers or out of town guests and it's still amazing. The crew...More

Thank kbdelapaz
Reviewed September 3, 2017

We took our family on the Sunset Sail a few weeks ago. It was lots of fun. The crew was very friendly and the sunset was amazing.

Thank lparker220
Reviewed September 3, 2017

I made the mistake of buying tickets six days in advance. 3 days before the trip, the weather report went from great to horrible. Hurricane Harvey was coming up this way and was going to dump a bunch of rain. I called them and explained...More

1  Thank stevear98
Bill M, Manager at Schooner Woodwind, responded to this reviewResponded September 6, 2017

Thank you for taking the time to provide your feedback, we hope that many future customers take the time to read your review as well as this response. You are absolutely correct that we do uphold our policy of sailing rain or shine unless the...More

Reviewed August 30, 2017

We went for my husband's birthday last Wednesday for a sailing race but due to no winds it was cancelled. However we had such a blast sailing into the sunset, it was just gorgeous. A perfect ride for a special occasion or if you are...More

Thank MyTicklefeet
Reviewed August 29, 2017 via mobile

My wife and I did the boat and breakfast. When I called to make the reservation I was told exactly what to expect. The sunset Cruise was beautiful. The crew was extremely helpful and attentive. They noticed I had an empty drink in my hand,...More

Thank MillerOD
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Ask a question
Questions & Answers
Kimbercat S
June 6, 2016|
AnswerShow all 2 answers
Response from Bill M | Property representative |
Guests have the opportunity to help raise the sails, steer the schooner, and ask questions. You also can just sit back and relax! Captain may have suggestions of where best to take a lesson locally. Weight is not an issue... More
September 2, 2015|
AnswerShow all 3 answers
Response from BethLeath | Property representative |
Thank you for your question. Yes we are sailing on Labor Day from 10am-12pm, 12:30-2:30pm, 3-5pm & 5:30-7:30pm. The cost is $44/adult, $42/senior (over 60) & $27/child (under 12). Please visit our website to purchase... More
July 1, 2015|
AnswerShow all 8 answers
Response from 2118burke | Reviewed this property |
There is another nice boat out of Annapolis - it's a Priate Ship - specifically for kids. They dress up and it's great for small children. The Windwood for the evening cruise was mostly adults so not sure about daytime... More