Review Highlights
“The captain and crew of the Woodwind were friendly and fun but still maintained a safe boating experience.” in 76 reviews
“We sailed through Annapolis Harbor, past the Naval Academy, up the Severn River, and into the Chesapeake Bay.” in 13 reviews
“We got to take a hold of the boat wheel and guide it with a little help from the captain on board.” in 32 reviews
Location & Hours
Annapolis, MD 21401
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Amenities and More
About the Business
Business owner information
Captain Jennifer K.
Think about adding a sailing cruise experience when dining in downtown Annapolis. Perfect to do before or after a lunch or dinner! Raise the sails, steer the boat or sit back and relax on our sailing tour. This is not your typical tourist attraction, we really sail and turn the engine off! Woodwind specializes in 2-hour public sailing cruises, up to four times daily from the Annapolis Waterfront Hotel. We also have special events like dinner cruises, foodie cruises, and lunch cruises. On many weekends we offer wine tastings and weeknights we offer a variety of cruises. Monday's sunset sail are History focused, Tuesday nights we have beer tastings and Wednesdays are race night. We also specialize in private charters for corporate groups, company picnics, family gatherings, birthdays, reunions and cocktail parties. We also feature an interactive and challenging team building program where "guest" crew learn how to sail and race our schooners with their colleagues.
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Overall rating
132 reviews
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- Terry A.Milford, DE011Apr 15, 2024
A day spent on either Woodwind Schooner is always the best. But this Sunday it was a specialty music sail with Tony Lucca with perfect sailing weather with sun, blue skies and wind to make it even better. Captain Jen at the wheel and a great crew of Delaney, Michael & Jacob made it a perfect experience for all.
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Oh no 0 - Sep 2, 2023Updated review
If you need a different idea for date day look no further than the schooner woodwind. 2-hour sales out on the Chesapeake Bay out of downtown Annapolis with all the comforts of boat ownership without any of the headaches. Well worth every penny, especially if the weather is nice
The cruise super nice and they serve drinks on board both alcoholic and not. It's a fair price for what you get and the capstone for any day date in Annapolis.
Highly recommended as we have been three or four times now and look forward to it annually. The owner and her staff could not be more friendly.
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Jennifer K.
Sep 6, 2023
Thank you so much for the wonderful review! I love your comment about boat ownership, "all the comforts of boat ownership without any of the headaches". Someone did the math the other day and said if they owned a 30-foot sailboat, and paid $3000 for dockage, that is equivalent to going out 30 times on the Woodwind with a couple of drinks and gratuity. That's almost once a week for the whole season.
Thanks for your support after all these years- Captain Jen.Jun 23, 2019Previous reviewWe loved this totally; our second time and our first since 2017.
A large part of what made it excellent was nothing that the captain or crew could control - the weather. Sunshine, blue skies and a fresh breeze made it just a perfect day to sail. Just the right mix of seamanship and comedy from the experienced crew helped, with some basic tour guide info added for good measure.
As my Facebook post said, all of the pleasures of sailing without the cost of boat ownership or boat insurance. Well worth the time and money to spend two hours away from the shops, restaurants and whatnot of Annapolis. - Jun 11, 2023
We had a fantastic time on the Schooner.
This is a sailboat so you will be exposed to conditions like the sun, etc. The weather for our sunset ride was perfect.
We were seated next to the captain who was very nice and knowledgeable. However, this isn't a boat ride where the captain gives history or points out landmarks, etc. It's a ride, not a tour.
I would love to go back for a specialty cruise-they have beer cruises, history ones, etc that sound like fun.
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Pat B.Los Gatos, CA34205Jun 16, 2023Incredible sail with great owner Captain Jen. We are sailors and will sail for a week here but wanted some local knowledge so we signed up for the tour. We had all kinds of weather and had all 5 sails up. Customers get to help with the sails and steer should they want to. Jen gafe is lots of information on where to sail and places to eat for our week here.
The boats are awesome and very impeccably maintained.
I highly recommend the trip.
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Omar S.Miami, FL061May 8, 2023What an amazing experience!!
Captain Jennifer and her Crew were very accommodating, friendly and true professionals.
You're allowed to volunteer and join in on raising the sails or sit back and relax and take in the Chesapeake Bay.
Highly Recommend It...A+++Helpful 0Thanks 0Love this 0Oh no 0- Jul 16, 2022
While in town visiting friends, they surprised us with a sunset cruise. The breeze was perfect and the beers were ice cold. Our staff was funny and educational as they answered all sorts of questions from the other guests. Also had the pleasure of helping raise the sail which makes for a good story.
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Tiffany B.Dallas, TX3929Jun 25, 2023We had such an amazing time on our trip! Even though our trip was cut a little short due to lightning in the area, I felt like the captain had our best interest at heart by delaying our departure. I would highly recommend this experience to anybody. The staff on the boat is also amazing.
Helpful 0Thanks 0Love this 0Oh no 0- Kim H.Manassas, VA1112Jul 19, 2023
I scheduled this for my companies Executive Team and it was amazing. We sailed the 4:00 - 6:00 PM Private. The process of scheduling, ordering food, sailing was TOP NOTCH. Our Captain Jen and her crew took great care of us and made sure we had the perfect sail. I would highly recommend this from a personal sail to a team/company sail.
KIMHelpful 0Thanks 0Love this 0Oh no 0 - Dr V.Owings Mills, MD0137Sep 11, 2023
Enjoyed sailing around the bay with this crew. Relaxing 2 hours on the water. Everyone was friendly. Passenger participation was a nice touch.
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