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Schooner Woodwind

80 Compromise St, Annapolis Marriott Waterfront Hotel, Annapolis, MD 21401-1810
+1 410-263-7837
Review Highlights
Great No Matter What The Weather

It rained for about an hour before our "sunset cruise" and was still sprinkling when we boarded the... read more

Reviewed 1 week ago
Shannon S

So enjoy this! Have been on the ship several times. A must when out of towner's visit. Have... read more

Reviewed 2 weeks ago
Paula H
Andrews AFB, MD
via mobile
Read all 231 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 good12%
  • Average2%
  • Poor1%
  • Terrible2%
Travellers talk about
“sunset cruise” (29 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
+1 410-263-7837
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Reviews (231)
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1 - 10 of 229 reviews

Reviewed 1 week ago

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

Thank Shannon S
Reviewed 2 weeks ago 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

Thank Paula H
Reviewed 2 weeks ago 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

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

1  Thank Sarah I
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

1  Thank AW0710
Reviewed 23 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.

Thank fclarkeiv
Reviewed 22 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

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

Thank vacaexpert777
Reviewed 4 May 2017

My husband and I had been wanting to go on a sail boat for a while now, we finally found a location and price we were happy with. The only issue was that the boat didn't go far, for a 2 hour sail we stayed...More

Thank FFXTravelers
Bill M, Manager at Schooner Woodwind, responded to this reviewResponded 5 May 2017

Hello FFXTravelers, Thank you for choosing the Schooner Woodwind for your first sailing experience. Sailing is a different experience with Mother Nature every time you step aboard. We offer a true sailing experience in the two hours that we have our guests on board. On...More

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....More

1  Thank EPBOL
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Questions & Answers
Kimbercat S
6 June 2016|
Answer Show 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|
Answer Show 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|
Answer Show 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