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Schooner Woodwind

Closed Now: 10:00 am - 6:30 pm
Open today: 10:00 am - 6:30 pm

Schooner Woodwind
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Certificate of Excellence
Traveller Overview
  • Excellent84%
  • Very good11%
  • Average2%
  • Poor1%
  • Terrible2%
Travellers talk about
“sunset cruise”(35 reviews)
“hour sail”(14 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: 10:00 am - 6:30 pm
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80 Compromise St, Annapolis Marriott Waterfront Hotel, Annapolis, MD 21401-1810
+1 410-263-7837
Reviews (272)
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All reviews sunset cruise captain and crew hour sail beer and wine wedding crashers bay bridge bag of chips amazing ride wednesday night relaxing afternoon two hours great sailing perfect weather sailing experience lots of fun naval academy visiting annapolis
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1 - 10 of 270 reviews
Reviewed 1 week ago

My husband, mom, and I had a great time sailing on an overcast Wednesday evening. The crew was friendly, interactive, and answered all of our questions. There were only five of us out that day, so we got the benefit of a more intimate setting....More

Thank Stephaniegeeze
Reviewed 2 weeks ago via mobile

Day trip spent in Annapolis, Md. my husband and I and six friends. We did the sunset cruise with a full moon. It was perfect. Captain and crew so friendly and attentive. Plan ahead with your calendar (for full moon) and then book according with...More

Thank Ohtotravelforever
Reviewed 4 September 2018

Although it was cloudy and we didn't actually see a sunset, the ride was great, crew was informative of the area, and kept our glasses full

Thank deb j
Reviewed 30 August 2018 via mobile

Great way to beat the heat! Crew was friendly and encouraged guests to assist and steer. We only had 8 guests on the vessel. Very reasonably priced. You receive a soft drink and a snack included!

Thank lorij50
Reviewed 29 August 2018

The crew of the Woodwind were welcoming, engaging and hospitable. They made the voyage a great deal of fun, allowing our younger sons to steer the boat and had our older daughter help pull down the mainsail. The boat is well equipped with restrooms and...More

Thank BurningYurt
Reviewed 11 August 2018

The skipper on our cruise started sailing when she was four years old. Her confidence, knowledge, and respect from the three-person crew show it. The paying guests get to help raise the sails, but the crew run the vessel, trim the sails, and "answer up"...More

Thank Russell R
Reviewed 8 August 2018 via mobile

My fiancé and I travelled to Annapolis for a few days just to enjoy the food, scenery, and bars. We had planned the trip prior to our engagement but there could not have been a better way to celebrate than this sunset cruise. We went...More

Thank brogalb
Reviewed 27 July 2018 via mobile

Planned an afternoon sail/tour, the boat conveniently leaves from the center of town located next to dinning, pubs. All within walking distance of the academy. Captain and crew do a great job making an tour fun and a bit adventurist, drinks and craft beers offered...More

Thank David J
Reviewed 22 July 2018 via mobile

We enjoyed our ride on this sailboat. The bay was beautiful. My son was able to steer the boat for a time. Worth our time and reasonable fee.

Thank Excursion234316
Reviewed 21 July 2018

If you are going to be in Annapolis, a must is taking the Schooner Woodwind out on the Chesapeake! Captain Jenn and her crew were just the best! Hwe knowledge about the waterways was amazing and you felt confident in her abilities at all times!...More

Thank Donna P
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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