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Schooner Woodwind

Closed Now: 9:00 am - 5:00 pm
Open today: 9:00 am - 5:00 pm

Schooner Woodwind
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Certificate of Excellence
Traveller Overview
  • Excellent85%
  • Very good10%
  • Average2%
  • Poor1%
  • Terrible2%
Travellers talk about
“sunset cruise”(36 reviews)
“beer and wine”(10 reviews)
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...more
Closed Now
Hours Today: 9:00 am - 5:00 pm
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Suggested duration: 2-3 hours
80 Compromise St, Annapolis Marriott Waterfront Hotel, Annapolis, MD 21401-1810
+1 410-263-7837
Reviews (273)
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All reviews sunset cruise captain and crew beer and wine wedding crashers bay bridge bag of chips wednesday evening amazing ride relaxing afternoon two hours great sailing perfect weather sailing experience hour trip lots of fun naval academy visiting annapolis
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21 - 30 of 271 reviews
Reviewed 19 June 2018 via mobile

Obviously grand weather enhances the experience, but rest assured that the crew of Woodwind will optimize your enjoyment. You are allowed—- and encouraged to take the helm for a few minutes, if so inclined. The views of Annapolis, the Naval Academy, and the Bay Bridge...More

Thank mhowar17
Reviewed 19 June 2018 via mobile

I had a wonderful sail with Captain Jen. Not only did we get close to the Bay Bridge but Captain Jen was a font of information about Annapolis and the Naval Academy. I highly recommend this fun adventure!

Thank nikkius2016
Reviewed 18 June 2018 via mobile

We always have a great time when we’re sailing with the Woodwind crew. It’s a great opportunity to get some beautiful photos, too!

Thank Vanessa F
Reviewed 11 May 2018

Picture a hot spring afternoon, reasonable winds and a fabulous schooner with a friendly crew then add two couples whose ladies both shared a birthday. What a fabulous experience, sailing out of Annapolis to the Bay bridge and back achieving 10.2 knots under full sail....More

Thank bedonboy
Reviewed 22 January 2018 via mobile

I had the opportunity to partake in two sailings with two groups of visiting friends. One was the Wednesday night race where not only did you participate in the two attraction schooners racing but also got to view the Wednesday night races of the Annapolis...More

Thank kevin12400
Reviewed 26 December 2017 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 10 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

1  Thank mquest
Reviewed 26 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 lisabN5049RG
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
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Questions & Answers
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Grady J
20 June 2018|
AnswerShow all 2 answers
Response from nikkius2016 | Reviewed this property |
You must be able to take a step up or down once on board. There are lots of crew members to help you!
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