Reviewers frequently praise the friendly, knowledgeable crew and the vessel's comfortable handling in various conditions. Common highlights include interactive sailing opportunities, onboard bars, and scenic views of the Chesapeake Bay. However, several low-star reviews criticize the strict no-refund policy for bad weather, noting the lack of shelter or rescheduling options. Additionally, some customers reported feeling ignored by staff during group events or facing unexpected issues with service animals.
Data from Google, last updated October 25, 2026.
Reviews from Google, shown as published (original wording, unedited).
Friendly and informative crew. Solid craft.
Thank you for sailing Schooner Woodwind! We appreciate your review, and we hope you will come back for another enjoyable cruise!
This was our 2nd cruise on the Woodwind and it was again just beautiful. The captain and crew were very friendly, and very knowledgeable about the area and, of course sailing. It will always be on our to do list when in Annapolis!
Thank you for coming back! We are so happy that you enjoyed your cruise and our wonderful staff. We look for to again sailing with you when you are back in Annapolis!
Perfect evening sail! The the capt and crew were fantastic, very knowledgeable and interactive, plus great bartenders!
We are so happy you enjoyed your sail and our awesome staff! We hope you can join us again in the near future!
Incredible day sailing on this Schooner. Friendly staff.
Thanks for sharing your photos! We hope you can soon come back for another incredible day of sailing and for more fun photos!
Always an amazing experience! Crew is so friendly and informative, eager to get guest involved and making sure everyone has a good time. Highly recommend this one of a kind experience on the Bay!
Thank you for coming back to enjoy another amazing sailing experience ! We are so glad that you enjoyed our remarkable crew and we look forward to seeing you on another future sail!
What a great experience! We had some weather—wind and rain. It’s worthy to note that the boat was comfortable and properly managed in the wind. It was a GREAT ride. It was smooth, not bumpy or requiring extreme lean/keel. If you sail in the rain, bring proper rain gear! You will be wet even with all the world’s ponchos! The crew was PHENOMENAL. Would sail or hang out with these guys any day!!!
We are happy you could have such a great time despite the weather. We agree that our crew and captains are the best. We hope you can join us all again, and maybe in better weather conditions (but windy days are fun)!
Fun schooner boat ride! Friendly staff. Bar available onboard. Take a jacket...it's very breezy out on the water. Had a great time!!
So glad to hear you had a great time! Thanks for the great review. Hope to sail with you again
Fun experience. Crew was excellent. Sunset was beautiful and perfectly timed by the Captain/crew.
Glad to hear you had a good time aboard the Woodwind and an amazing sunset! Hope to see you again.
While the wind did not cooperate the sunny day offered just enough breeze to enjoy a nice couple hours on the water.
Thank you so much for sailing with Schooner Woodwind. We hope the winds are up during your next sail !
We had a fantastic time sailing with the crew and guests! It was a very relaxing evening. The crew was a lot of fun! Top notch customer service! And a beautiful sunset to top it off!
We are so glad you were able to relax and have fun on your sail! A beautiful sunset is "icing on the cake"! We hope that you can soon sail with us again!