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    Schooner Woodwind

    4.3 (159 reviews)
    Closed 10:00 am - 6:30 pm
    Updated 2 months ago

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    Woodwind returning.

    what fun! a must- do if you're visiting Annapolis. Trips are 2 hours, see some cool sights, and you can take the helm (or hoist a sail) if you'd like. The crew and Captain were SO accommodating.

    A 21 year tradition continues! .... each year on or near our wedding anniversary we take a cruise aboard the sailboat we were married on. Yesterday was our day to celebrate sharing life's journey together! The winds were blowing perfectly which lead to a fantastic afternoon sailing adventure! Looking forward to many more years of cruising with my beautiful bride aboard Schooner Woodwind: Annapolis Sailing Cruises ... Founded and operated by the Kaye Family since July 1993 ... The Schooner Woodwind is a first class business that provides outstanding service and an exceptional sailing experience. We might be slightly bias but if you are visiting Annapolis we wholeheartedly recommend Schooner Woodwind: Annapolis Sailing Cruises! Check them out on the web at: https://schoonerwoodwind.com/

    Sails going up
    Pat B.

    Incredible 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.

    Maggie H.

    It's always a wonderful experience sailing with Schooner Woodwind and being able to watch the Blue Angels from the water was extra special! Captain Jen and the crew were engaging and kind.

    Standing beside boat at dock before setting off
    Helen T.

    Went on a two hour 11am tour Sunday Memorial weekend, booked a week in advance. I was a little concerned about getting the reservation in time since the bookings open a week in advance, but I was able to get two tickets with several openings remaining within an hour after reservations opened. The four person crew was communicative during the sailing portions, asking for volunteers to help raise and lower the sails, and chatty/friendly while we sailed around the harbor. There were 20-25 other people on the boat with several children, and I appreciated that the crew especially engaged with them (letting them steer the ship). We motored in and out of the dock, but otherwise sailed for the majority of the time on the boat. Ticket came with a free drink. It was my first time on a sailboat, and I enjoyed the chitchat with the staff and the tour the captain gave of the sights. Great experience - worth the $60+ ticket for an Annapolis summer morning! Remember to wear sunscreen. (They also offer life jackets for those interested.)

    Beautiful ship and great crew! Was a wonderful first time sailing experience will definitely want to do again! Highly recommend! They sail through November in October would be beautiful to see the autumn foliage from the sailboat!

    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.

    The view from the sailboat
    Grace R.

    This was nice. Followed social distancing measures at line up and on boat. Thing is we thought we were buying a tour. Turn out this was just a sail ride and we made several circles lol. Very quiet should have some sort of music on board. Bought a bottle of champagne for $28 which was good. Can also tip crew online.

    Colton D.

    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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    3 years ago

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    Jennifer K.

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    9 months ago

    Nice relaxing sunset sail. 2 hours fly by with a tour of the bay and interesting facts about the area and its history.

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    8 months ago

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    1 year ago

    This is wonderful sailing experience. A definite must do while visiting Annapolis. The crew, boat and tour were all exceptional.

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    Jennifer K.

    Love that you mentioned us as a "must do". Thank you!

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    9 months ago

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    3 years ago

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    11 months ago

    Great crew, great boat, and great evening on the water! Who knew that our boat was the one they used in The Wedding Crashers?!!!

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    4 years ago

    Awesome end to our vacation in Annapolis. Very friendly captain and crew, we had an amazing time.

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    7 years ago

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    Jennifer K.

    Thanks so much for the great review! Glad you had a blast.

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    6 years ago

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    4 years ago

    Perfect night with the perfect crew! Mickey, Ed and Sophia were so accommodating and knowledgeable. Highly recommend the sunset sail!

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    3 years ago

    Too much talking. If no wind they just motor around Naval Academy. Barely got to mouth of Severn in two hours.

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    Page 1 of 4

    Ask the Community - Schooner Woodwind

    Review Highlights - Schooner Woodwind

    Our Captain Jen and her crew took great care of us and made sure we had the perfect sail.

    Mentioned in 90 reviews

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    Schooner Woodwind - boating - Updated May 2026

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