Cancel

    Open app

    Search

    Schooner Woodwind

    4.3 (160 reviews)
    Open 10:00 am - 6:30 pm
    Updated 3 months ago

    Services - Schooner Woodwind

    Boat charters

    Schooner Woodwind Photos

    You might also consider

    Recommended Reviews - Schooner Woodwind

    Your trust is our priority, so businesses can't pay to alter or remove their reviews. Learn more about reviews.
    Yelp app icon
    Browse more easily on the app
    Review Feed Illustration

    Reviews With Photos

    Dana J.

    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.

    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.

    See all

    3 years ago

    Helpful 1
    Thanks 0
    Love this 0
    Oh no 1

    3 years ago

    Fantastic day on the water with Captain Jen and her crew! If you are in Annapolis, I highly suggest you take a sail with this team!!

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0

    3 years ago

    Captain Andy and Crewmembers Ed and Nellie were personable and skillful sailors. Made for an enjoyable afternoon on the Chesapeake Bay.

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0

    10 years ago

    Helpful 13
    Thanks 0
    Love this 8
    Oh no 0
    Photo of Kitti T.
    128
    43
    52

    11 years ago

    Helpful 2
    Thanks 0
    Love this 1
    Oh no 0
    Photo of Dylan S.
    18
    47
    21

    6 years ago

    Business owner information

    Photo of Jennifer K.

    Jennifer K.

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0

    8 years ago

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0

    7 years ago

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0

    6 years ago

    Business owner information

    Photo of Jennifer K.

    Jennifer K.

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0
    Photo of Brad B.
    151
    153
    16

    9 years ago

    Helpful 0
    Thanks 0
    Love this 2
    Oh no 0
    Photo of Jeff G.
    24
    31
    3

    6 years ago

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0

    9 years ago

    Helpful 4
    Thanks 0
    Love this 1
    Oh no 0

    4 years ago

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0

    4 years ago

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0
    Photo of Michelle S.
    147
    106
    36

    4 years ago

    Was a great time! The captain and crew were very attentive and informative. It was not too crowded with covid and I felt safe

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0

    5 years ago

    Business owner information

    Photo of Jennifer K.

    Jennifer K.

    Helpful 1
    Thanks 0
    Love this 0
    Oh no 0

    4 years ago

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0

    4 years ago

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0

    9 years ago

    Helpful 0
    Thanks 0
    Love this 1
    Oh no 0

    9 years ago

    Helpful 1
    Thanks 0
    Love this 0
    Oh no 0

    7 years ago

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0

    4 years ago

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0

    7 years ago

    Helpful 1
    Thanks 0
    Love this 1
    Oh no 0

    7 years ago

    Helpful 1
    Thanks 0
    Love this 0
    Oh no 0

    8 years ago

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0

    7 years ago

    Business owner information

    Photo of Jennifer K.

    Jennifer K.

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0
    Photo of Corky M.
    13
    17
    18

    8 years ago

    Helpful 1
    Thanks 0
    Love this 0
    Oh no 0

    17 years ago

    Helpful 5
    Thanks 0
    Love this 6
    Oh no 0

    19 years ago

    Helpful 4
    Thanks 0
    Love this 0
    Oh no 0

    13 years ago

    Helpful 3
    Thanks 0
    Love this 2
    Oh no 0
    Photo of Juliet A.
    1536
    1200
    1475

    13 years ago

    Helpful 2
    Thanks 0
    Love this 0
    Oh no 0

    16 years ago

    Helpful 2
    Thanks 0
    Love this 1
    Oh no 0

    9 years ago

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0

    12 years ago

    Helpful 1
    Thanks 0
    Love this 0
    Oh no 0

    10 years ago

    Helpful 1
    Thanks 0
    Love this 2
    Oh no 0

    15 years ago

    Helpful 1
    Thanks 0
    Love this 1
    Oh no 0

    8 years ago

    Helpful 1
    Thanks 0
    Love this 0
    Oh no 0

    13 years ago

    Helpful 0
    Thanks 0
    Love this 1
    Oh no 0
    Photo of Amanda M.
    88
    39
    41

    12 years ago

    Helpful 1
    Thanks 0
    Love this 0
    Oh no 0

    12 years ago

    Helpful 0
    Thanks 0
    Love this 1
    Oh no 0

    Page 2 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 91 reviews

    Read more highlights

    You might also consider

    Annapolis Electric Boat Rentals

    Annapolis Electric Boat Rentals

    4.7
    (42 reviews)

    I heard about Annapolis Electric Boat Rentals through another Eastport/Annapolis event. Greg and…read moreSherry were terrific to work with before and after I rented their boat online. At the dock, Greg gave me and my family a quick, but thorough review of the boat and its safety features. The boat itself was spotless, and silent during the cruise. Cruising Annapolis Harbor and Spa Creek was a delight. A wonderful day, and a great value on the water. Thank you Greg and Sherry!!! I will be back.

    On April 5, 2026, I made online reservation for a boat at 10 AM April 6, and was charged $423 at…read morethat time. At 8 AM the following day, I received a voicemail, an email, and a text message from the company stating that they were closed Monday and I should not have been allowed to make a reservation via their own website,. Obviously there would be a full refund, and they were very apologetic. I never received the refund and contacted them twice more during the next six days. Today I received an email from Benjamin. Tiederman stating that I would only be refunded 50%, which would not be received for another five days. This is fraud and theft, Along with basic incompetence and lack of ethics. I had to eventually submit a charge back to my credit card company, which will cost them extra money in fines instead of doing what they stated they would do. I've never left a negative review on any site so congratulations Annapolis electric boat rentals.

    Pirate Adventures on the Chesapeake

    Pirate Adventures on the Chesapeake

    4.9
    (110 reviews)

    Exceptional entertainment for children - the cast is great, funny and interactive. The storyline…read moreholds so well and keeps the kids engaged the whole way through, with many surprises and adventures on the way. One of the best family adventure in the US.

    Pirate Adventures on the Chesapeake was a really cool adventure for my kids. They loved all aspects…read moreof it! The adventure starts with a phone call. This isn't the type of adventure you can show up to on a whim. You have to schedule a visit in advance. I scheduled a date and time over the phone. They took my credit card info, a contact number and my kids' names. The first date I scheduled was cancelled due to inclement weather. Pirate Adventures called and cancelled the adventure about three hours prior to when it was supposed to start. I elected to reschedule right then. I was instructed to arrive a half hour before our adventure so the kids could get their faces painted and pick out a sash. We parked on the street a few blocks away not realizing they have a parking lot. We checked in, the kids were given name tags with their name and an alliterative adjective (ie Zig Zag Zora and Kung Fu Kieran) and then reported to the face painting and sash picking area. After face painting kids and adults boarded the boat and the Chesapeake part of the adventure began. The captain went over a few safety measures with the adults while his assistant went through guidelines with the kids. The adventure has a whole story with different parts involved that kept the seven kids on our adventure entertained. Ages ranged from probably three to fourteen. These parts included a map search, treasure hunt, key finding expedition, pirate fight and a final pirate bounty quest. For the adults, we just hung out under a shaded portion of the boat. I got up to interact with my kids a few times and to snap some pictures. Mostly I just enjoyed the boat ride. The whole adventure lasted almost two hours (counting face painting). If you have kids that love to pretend and don't mind riding a boat, Pirate Adventures on the Chesapeake might be right up their alley.

    SailTime - Annapolis

    SailTime - Annapolis

    4.7
    (10 reviews)

    I'm a member of the Flyer 9 PowerTime boat at SailTime Annapolis. I love SailTime! I evaluated…read moreseveral other options when I joined and SailTime had the best fleet options by far. The Annapolis location is especially great. There are regular social events, a great clubhouse, and incredible team to support everything. SailTime is remarkable at how quickly they address reported issues. Just yesterday I reported a few minor issues during my check off and they are already scheduled to be fixed tomorrow! Sailtime is really the best way to boat in my opinion. It's so nice to not have to worry about maintenance, winterizing, and all the other things that typically come with boat ownership. It's far cheaper than owning. Some things still could use improvement. Sailtime Plus, while extremely promising, isn't the most straightforward to use/book. I didn't hear back when I inquired about using it through the site. Building a better automated system for using SailTime Plus and checking availability at other locations would be awesome. I'd even plan trips around which locations had availability. There is one thing I would change if I ran SailTime. An additional charge pay-per-use option to have the boat prepped, stocked with sheets, refueled, docked, rinsed, and covers put back on. Not sure if there is enough interest in something like this to justify it but I'd definitely use and love it! Overall, I love my membership. I was worried I wouldn't feel like I got enough time on the boat but I don't feel like I've had any issues finding availability. I get plenty of use for my satisfaction. There are lots of days (especially weekdays) when the boat is completely unused. The other members are wonderful and take great care of the boat. I highly recommend joining!

    Just completed my ASA 104 with Sailtime Annapolis and Captain Gary. I can't say enough about the…read moreexperience. Everyone was superb, professional, organized, and really went out of there way to make the entire 3 day / 2 night course such a great time. Capt. Gary was the best: a patient teacher, knowledgeable sailor, a kind, humorous soul, and really instilled fun and learning into the course. The 40' boat was clean, well-equipped, and sailed great. My crew mates were excellent company. Accommodations were very comfortable -- a great sailing vessel. Upon returning to port (after slogging through a dreary, cold, rainy last day), Tammy had prepared delicious Crab Bisque and cookies! What service! Can't say enough about the experience!

    Schooner Woodwind - boating - Updated July 2026

    Loading...
    Loading...
    Loading...