Schooner Woodwind Sailing Cruises — Attraction in Annapolis

I should be up front that I can only comment on the process of scheduling and embarking on a sail; I did not sail on the ship itself.

I had a sail set for the weekend of the Annapolis Boat Show, to depart at 5:45 p.m. Unfortunately, during the day of the sail, Annapolis, and all of the Chesapeake area, experienced a severe high tide that caused flooding in and around the area of the Annapolis City Dock. As a result, the Boat Show was canceled early, and when my party arrived around 5:00 p.m., we weren't exactly sure where to go.

The ticket contained instructions detailing which slip to look for, but as someone who has never been to the Annapolis Dock, it was very difficult for me to figure out where that slip was, as there was no address or directions. It was just "US Sail Boat Show - Dock F2". Which would probably have been enough, if anyone from the Boat Show had been able to help us, but they had all already left, or were busy trying the mitigate the flooding.

We tried calling Woodwind to clarify where we should be, but no one answered; their ticket office was closed for the weekend, and there were no alternate numbers provided.

I decided to check my email, to see if updates had been provided, and Woodwind had in fact sent an email noting the state of the boat show. However, to clarify they only gave vague directions, saying things like "the hotel closest to the yacht basin parking lot." As mentioned above, we were not at all familiar with Annapolis, so this could have been any of several buildings, and because large portions of the surrounding streets were flooded or closed off by police, checking on each of them was a difficult prospect. Without going into detail, we gave up trying to find the dock at about 5:50, when we were pretty sure the boat would have already left without us, as the follow-up e-mail explicitly noted that the boat was still sailing.

I feel like there was very poor support for this event. I am sure that hosting sails during the Boat Show complicates matters, but at no point in either the original ticket or the follow-up e-mail was sufficient detail given to make things easier. There are no addresses or step-by-step directions, which feels like it would be sort of expected for an event like this. And to boot, there was no way to talk with anyone on the Woodwind team, as their ticket office was closed and no other number listed. I would think that there would be a way to reach someone at the company whenever there is a sail scheduled, to help answer questions and provide information for unforeseen events.

Based on the above, I would advise being cautious about sailing on the Woodwind during a special event if you are not an Annapolis native, or at least familiar with the area. Their support was nonexistent, and does not feel like a professional business. I am sure the boat and sail themselves are wonderful, but getting to them, for me at least, was unpleasant and...

I’m writing this review to help future guests be aware and to share a recent disappointing experience I had regarding your ticketing process. Back in August, I purchased two tickets for the Sunset Sail. Unfortunately, the second guest was unable to attend. I arrived at the dock two hours early to explain the situation to Joe. I didn’t request a refund—knowing the tickets were non-refundable—but asked if the unused ticket could be honored on a standby basis for a future sail. Joe agreed and advised me to call a few days in advance when I was ready to rebook. Three weeks later, my parents were interested in experiencing the Sunset Sail after hearing how much I enjoyed it. I called Joe to redeem the standby ticket and to purchase an additional ticket for the second person. Before making the purchase, I asked specifically if both guests would be able to board. Joe assured me they would. However, on the day of the sail, my parents arrived early (around 4:45 PM), only to be told by Joe that only one confirmed ticket existed, and the second guest would have to wait to see if someone didn’t show up. By 5:20 PM, I received a message from my mother saying they would not be able to board because they had a standby ticket. I immediately called Joe for clarification. Instead of acknowledging the confusion or taking accountability, he referred me to the standby policy and offered vague excuses. As a consolation, he mentioned the both tickets could now be used on any future date—but unfortunately, the moment was already lost. Why would I have knowingly purchased only one ticket if I had been told in advance that the second person might not be able to board—especially for what I understand is your most popular sail? This experience not only wasted my parents’ time but also reflected poorly on your customer service approach. While the boat, crew, and scenery were truly fantastic during my own visit, this experience has left me disappointed. It’s not about the money—it’s about trust, communication, and how guests are treated. I hope you take this feedback seriously and use it to improve how such situations are handled...

TERRIBLE CUSTOMER SERVICE Really upset with our experience with these guys today. We planned a last minute trip to Annapolis and we were hoping to get on one of the boats as stand-by passengers. We went to the check in desk at 11 am to see how we could do this. We were told to show up 30 minutes prior to the time of the tour we wanted to take. As instructed, we came back at 3:30 to wait and see if there was availability for a 4 pm ride. At 4:02, we were told there were two tickets available. We paid, got on the boat and were really excited things worked out! At 4:15 right when we were about to leave the dock, two customers who had bought tickets earlier strolled in with Starbucks that they clearly just bought showing absolutely no urgency despite being 45 minutes late to the tour. After a bit of confusion, we were asked, in front of all of the other passengers, to get off the boat. My wife and I were mortified. All the other passengers were extremely displeased not only that they were leaving late, but that this company showed absolutely no respect. Their company policy seemed to not exist up to this point and the owner of the company was the one who personally had the moments of indecision then decision to boot us from the boat. They took the time of all their customers to embarrass us and lose loyalty to all but 2 very late arrivers. The situation was handled very poorly and we look forward to our Chesapeake tour on the...