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Schooner Woodwind

80 Compromise St, Annapolis Marriott Waterfront Hotel, Annapolis, MD 21401-1810
+1 410-263-7837
Review Highlights
Harbor Cruise

Lovely Cruise! We were looking for a way to get out on the water while visiting Annapolis for the... read more

Reviewed 3 weeks ago
Kim D
Middleton, Wisconsin, United States
via mobile
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 25 October 2017
Read all 248 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%
Travellers talk about
“sunset cruise” (32 reviews)
“hour sail” (14 reviews)
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Hours Today: 10:00 - 18:30
80 Compromise St, Annapolis Marriott Waterfront Hotel, Annapolis, MD 21401-1810
Write a ReviewReviews (248)
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1 - 10 of 246 reviews

Reviewed 3 weeks ago via mobile

Lovely Cruise! We were looking for a way to get out on the water while visiting Annapolis for the first time as a USNA family. This was perfect for us! The younger boys loved getting to steer the boat and the peace and quiet of...More

Thank Kim D
Reviewed 25 October 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 9 October 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 25 September 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 18 September 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 17 September 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 9 September 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 3 September 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 2 September 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 5 September 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 30 August 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
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Ask a question
Questions & Answers
Kimbercat S
6 June 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
2 September 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
1 July 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