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Schooner Woodwind

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

Schooner Woodwind
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Traveller Overview
  • Excellent85%
  • Very good10%
  • Average2%
  • Poor1%
  • Terrible2%
Travellers talk about
“sunset cruise”(37 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
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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
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Reviews (273)
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All reviews sunset cruise captain and crew beer and wine bay bridge wedding crashers bag of chips wednesday evening amazing ride beautiful evening two hours great sailing hour trip perfect weather sailing experience naval academy lots of fun visiting annapolis
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41 - 50 of 271 reviews
Reviewed 6 August 2017

What a wonderful way to see the Bay when you don't own a sailboat. We thoroughly enjoyed our sail. The captain and crew of Woodwind were relaxed, knowledgeable of the area, and very friendly. The captain was really good about letting the kids in the...More

Date of experience: August 2017
Thank TXGreenGal
Reviewed 30 July 2017 via mobile

This was our second trip on the woodwind. We took the 11:00 sail before it got too hot. This is a great way to sail the Chesapeake the old fashioned way. Everyone got an opportunity to steer the boat which was great. We did not...More

Date of experience: July 2017
Thank Dave S
Reviewed 12 July 2017

It rained for about an hour before our "sunset cruise" and was still sprinkling when we boarded the Woodwind. The captain quickly got us out to better weather and a beautiful sail. We sailed all around the bay and several people were able to steer...More

Date of experience: July 2017
Thank Shannon S
Reviewed 4 July 2017 via mobile

So enjoy this! Have been on the ship several times. A must when out of towner's visit. Have always gotten Capt. Jen- she is great. When it's windy- what a ride!!!!! Calm is nice, too. Going for the July 4, 2017 fireworks ride...I'm too excited!!!...More

Date of experience: July 2017
Thank Paula H
Reviewed 2 July 2017 via mobile

We enjoyed a Father's day Sunday in the schooner and it was a good experience overall. It is a cool and different activity to do in Annapolis. The staff is very friendly. Our only bad experience was getting sea sick but that has nothing to...More

Date of experience: June 2017
Thank MelimarB
Reviewed 11 June 2017 via mobile

This is my second time riding on the Schooner Woodwind. I came previously on a bachelorette party, and enjoyed myself in both settings. The crew is accommodating and informative. The views are spectacular. It's a perfect price for the experience. Highly recommend the sunset sail!...More

Date of experience: June 2017
1  Thank 249sarahi
Reviewed 29 May 2017

My wife and I recently went on Woodwind for the sunset cruise and boat and breakfast. The sunset cruise was amazing, the staff was amazing, and the view of Annapolis from the boats path was breathtaking. The boat and breakfast was hosted by Captain Jen...More

Date of experience: May 2017
1  Thank AW0710
Reviewed 24 May 2017

Perfect chance to stay cool and see the sights without doing the work. If you are a sailor this is a kiddie ride. If you are a sightseer it is only 2 hours but packed with much fun.

Date of experience: May 2017
Thank fclarkeiv
Reviewed 23 May 2017

Decided to book a sunset sail. Tickets were bought a few days in advance.. It was a very cool and cloudy evening. The sail was delightful even though the weather was not. The crew was extremely accommodating and knowledgeable which made for a lovely evening....More

Date of experience: May 2017
Thank cesloan2
Reviewed 17 May 2017 via mobile

Great tour out on the water and enjoyable day. A little expensive but overall makes for a fun day out on the water in Annapolis(which is the way you need to see annapolis). Fun crew and they give you alcohol, what could be better

Date of experience: April 2017
Thank vacaexpert777
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Questions & Answers
Ask a question
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