I took my parents sailing with Woodwind over Labor Day weekend. The sun was still blazing hot for our 3pm sail but it was a perfect gorgeous day to be out on the water. Our captain Jen and her crew were very friendly, engaging and knowledgeable. They asked the patrons to help raise the sails and even steer the boat. As we sailed around Annapolis Harbor on the Chesapeake Bay, the captain pointed out different landmarks and some historical background. They have drinks on board to order, with a great selection of beer from local breweries. I'd recommend booking tickets at least few days early as I saw 3 out of the 4 sail time slots were marked as sold out. It'd also be a good idea to check weather forecast for the day you want to sail, as I heard they have a strict rain or shine policy. read more

Sailing on the Schooner Woodwind and watching the sunset was awesome! Everything about the experience, from purchasing the tickets, location, boarding, the captain, the ride, the snacks, the view- everything was nearly perfect. The tickets costs $37 per person which I thought was extremely reasonable and based on my experience, it was totally worth it. We purchased our tickets online one week prior to our departure. You have to make sure to buy your tickets in advance as they sell out pretty quickly. There are only 47 tickets per ride and based my my experience, they sell out. The boat initially seemed cramped. At first i thought, there was no way on earth that we could all fit on this boat and have a good time- so I was a bit disappointed and apprehensive. However once we were all on the boat it was not a worry. The boat was at 100% occupancy but it didn't feel overwhelming nor crowded. The captain was wonderful as were the crew. I don't think I can say the same about the music, which seemed like it was a combination of folk, pirate, and hymnals. I am open to all sorts of music but this kind was so -- not right. The views were spectacular! breathtaking! beautiful! and there was plenty of it. It did get a bit choppy at times but for me, the more the better- bring it on. I wouldn't recommend little children; for the safety of the kids and the sanity and experience for others on the boat. If there was a screaming kid on the boat I think I would have had thoughts of throwing the kid overboard. So note to all, leave the children at home. Very well run establishment. The ride was nearly flawless (minus the music). Everyone should experience sailing on the Woodwind. read more

Schooner Woodwind - Sailing the Bay - Boating Near Me - Annapolis, Maryland

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We did this tour on Saturday afternoon. It was a blast! Captain Mike and the crew were great, competent sailors with knowledge about the area. Comfortable and not cheesy. Great beer selection on board. We will definitely be back! Thanks! read more

This was our first time sailing, and our first time aboard the Schooner Woodwind. We were not dissapointed! The crew was amazing and very accomodating. The views of the Chesapeake are unmatched. And to top it all off, they have an amazing selection of craft beers onboard. We can't think of a better way to spend our anniversary :) Make sure you download the Foursquare app and "check-in" on your phone before you sail. They will give you a FREE koozy per check-in at the ticket booth which entitles you to one free craft beer per sailing. Have a wondeful time, just like we did! read more

Good experience for us since the weather was perfect. We did the sunset schedule so it wasn't frying us to bacon. My girlfriend was able to volunteer to steer the boat for a few minutes. They have a fun crew there. read more

Fun times on the Schooner on a beautiful August day!

We had a GREAT TIME and it was perfect weather! We went on the 11-1 cruise and it was packed - we were sitting butt to butt with each other, but at least we all got to sit. A few patrons get to volunteer to raise one of the sails, and during almost the entire cruise, patrons can take turns steering, which the kids on board seemed to love! They serve wine and beer / soda and a chip / pretzel / cookie. There wasn't a lot of narrative during the cruise (hard to hear across the whole boat) but if you had a question or wanted to chat, there were plenty of staff aboard to talk to and all were friendly. We plan to do this again - maybe the sunset cruise! read more

My wife and I stayed in Annapolis for a weekend and took the time to sail on the Schooner Woodwind II for the 2 hour afternoon trip. Boat was stunning, staff was extremely professional and personal. The skipper gave a tutorial on every step of raising the sails and getting under way! At first I was skeptical about the price of admission but once we got aboard it was evident that we were in for a treat. Totally worth the price! I highly recommend this trip if you've ever wanted to get out sailing. read more

We were packed like sardines. One large passenger needlessly kept walking back and forth in front of us stepping on our feet. The view was spectacular but not worth being trampled on. The staff was friendly but could have done a better job controlling the crowd. read more

It's $35 per ticket and I think it's worth it. Especially if you have friends from out of town or you're just looking for a 2 hr sailing excursion on a nice day - it's a good experience. The Woodwind Two is the boat they used in Wedding Crashers (not Woodwind One). read more

I took my kids last Monday for a 2 hour public cruise on the Chesapeake bay. I've always loved sailing and wanted to introduce my kids to it. We enjoyed it very much. There were about 30 passengers on board. The crew was very knowledgeable and attentive to our needs. My kids were able to help out with hoisting the sails, steering the boat, etc. All in all, an excellent experience. read more

Our captain, Jen, was awesome - fun, informative, accessible. The whole experience was wonderful - relaxing, entertaining, etc. Will definitely go back! read more

What a great time! Captain Mike Oh sails this 70'+ schooner like it's a dinghy. Views of Annapolis and the bay were beautiful. I recommend this for any visitor to the Annapolis area. read more

This was our third time out with these guys. We always have a good time. The crew is very friendly and engaging. They have quality craft beers on board which is a must for me. Great water views of Annapolis and the Bay Bridge. There is no better way to spend a couple hours on the Chesapeake than the schooner Winwood. read more

Yet another fantastic cruise with excellent customer service. Saturday was our 5th cruise with Woodwind & Woodwind II, and will not be our last. We got lucky with fantastic sailing weather - wind and sun. It was also the full-moon rise. We made it all the way out to the Bay Bridge! I can't say enough about how knowledgeable, helpful, and friendly the captains and crew always are. Looking forward to a multi-day sail one day! read more

I went with my family including two young sons and we all loved it. It was a great experience! Extremely friendly crew and Captain Jen was awesome. I highly recommend and will go back again for sure. read more

Great experience and beautiful evening. Was not over crowded, sat next to fun people and was blessed with an extraordinary sunset. The crew were very nice and helpful, sharing and pointing out various sights surrounding the bay. Will definitely return and bring out-of-town family to enjoy! Thanks for a great memory! read more

Been sailing with the Schooner woodwind folk for 12 years on and off and highly recommend it as a family activity or with folks visiting from out of town Friendly service great views a fun trip all round and you even get to steer the boat. Sam and family read more

As a local I thought we would try this tourist attraction. After purchasing our tickets in advance there was a terrible accident causing back ups all over the city. I called 3 times explaining that we were doing everything we could to get there. A ten minute ride turned into 40 minutes. We came running to the boat, 5 minutes past 530 to see it sailing away. No refund, no exchange. I understand no refund but to not be able to come on another cruise? Maybe a less crowded one. Seems a bit extreme. They did call back the next day, which is why I at least gave them 2 stars, however never again will I try this. I don't see it as worth the risk if there is something unforeseen that happens (terrible accident, weather, anything), they do not seem to feel the need to accommodate in any way. read more

As stated in other reviews the boats are overcrowded, to the point they feel unsafe at times. If you are near the end of the line you will get stuck in the middle of the boat, below the advertising tarp, with no breeze. The captain and crew do not seem to care that everyone has an enjoyable experience. Hated every bit of this experience. Would not recommend this company to anyone. read more

My wife and I embarked on our inaugural sailing adventure on the Woodwind last weekend. We chose the package that comes with a stay in the cabin overnight and breakfast the next morning. Overall the experience was new, fun and exciting. Our adventure started with the sunset cruise which is a roughly 2 hour sail into the Chesapeake Bay. During this time you can order drinks that for us were some local beer and wine options. Also, if you check in on Yelp you will get a coozie which gets you a free drink. The crew is extremely nice and accommodating. If you desire you may have the opportunity to drive the boat and hoist the sails. This was a great opportunity for us to see Annapolis from another vantage point on our first visit to the city. After docking we walked to dinner and came back to the boat around 11pm. The stay in the cabins is what you would expect for such tight living spaces. I will mention for those light sleepers out there like me there were many noises through the night and especially from one of our boat mates loud snoring. For me the most interesting part was to learn about sailing as I have almost zero experience. Discussing the filming of Wedding Crashers with the captain over breakfast the next morning was also a highlight due to such a unique history. Overall this will serve as a fun memory and one I would recommend to anyone visiting in the area, thanks! read more

They need a trash can lid. All of chip bags blew into the bay. Otherwise, completely epic experience.

Biggest downfall, is that if you don't arrive and stand in line at least 30 minutes prior, seating is difficult and the crew will not make any accommodations for you. If a couple of guests had scooted down or together just a little we would have been able to sit together (and there were just two of us). They do not offer any refunds or allow you to get on a different sailing. So we spent the entire cruise sitting by ourselves. Just disappointing and we were there 15 minutes prior to sailing as directed. read more

Sunset beer tasting sail - BY FAR my favorite thing to do in Annapolis. The crew is so amazing, and this was the boat used in Wedding Crashers! read more

VERY DISAPPOINTED that they would not allow us to exchange our tickets for another cruise despite the fact that it rained on July 4th and there were no fireworks. We called twice in advance to find out what our options were and were told that if the captain decided to sail, whether or not there were fireworks or rain, the boat would go out. Since it was advertised as a cruise to view the fireworks on July 4th, I felt they were not upholding their end of the deal. read more

Being out on the water was great - the crew was accommodating and entertaining, the sunset cruise went perfectly, and I got a couple free beers by checking in on Yelp before the cruise. Schooner Woodwind deserves 5 stars for the cruise. It was the service (or lack thereof) leading up to the cruise that I would rate at 0 stars, which did have an impact on my enjoyment of the cruise itself. Let me explain: I purchased 4 tickets for the sunset cruise, which very quickly sold out, and found out the night before the cruise that 2 of my guests would not be able to join me on the cruise. The website clearly states that there are no refunds, but I thought I would try my luck, so I called the company and left a voicemail around 7pm the night before the cruise, asking if they could list the tickets as available on the booking portion of their website, and if the tickets sold I would be off the hook, and if they didn't sell, I would still pay for the tickets. I never got a call back. When I showed up in Annapolis 2 hours before the sunset cruise, the woman at the ticket booth seemed to think that someone had called me back and discussed putting me in touch with the many people who had been calling them wanting to get on the cruise, even though it was sold out. Like I said, no one had actually returned my call. So with two hours left until the cruise, I asked the woman at the ticket booth to give my number to anyone else who may call looking for tickets for that night, and to change the sign outside the ticket booth from "SOLD OUT" to "2 tickets available" (I did note right before the cruise that she had changed one side of the sign, but not the other). In the end, I was not able to sell my two extra tickets. With four valid tickets in hand, my guest and I went back to the ticket counter to get our free beer coozies for checking in on Yelp before the cruise, and we got more hassle. We had 4 tickets, but only two check-ins on Yelp, so they would only give us 2 coozies (and therefore only 2 free beers) for our 4 tickets. So we stood there at the ticket booth and created 2 more Yelp accounts while the rest of the passengers boarded the cruise. Everyone had already boarded the cruise was waiting on us, so they just let us have the 4 coozies and 4 beers. And then we tried to have a good time. It would have been less frustrating/disheartening if they had just told us that they couldn't refund our money and tough luck, but instead they let us know about all the people who had been calling all day looking for tickets. We could have saved a lot of aggravation if the company had cared enough to put us in touch with one of the interested buyers. What company prefers two disgruntled customers to four happy customers? read more

Had a fantastic time on a Sunday afternoon sail. We will make this a regular activity when entertaining guests from out of state! Very reasonable price for the sail and for beverages on board. read more

Great. Crew was fun. If you ask you can steer the boat. Excellent value.

Wonderful experience. We lucked out on the weather, but really the crew was so nice and helpful that I don't see how we could have gone wrong. Captain Ken is really great, and he makes a big deal out of the kids--each one got to steer the boat. read more

The best experience in Annapolis! Once on board, you know that you are a part of the Woodwind family, and the views are breathtaking! This is an experience that is not to miss!!! read more

Took my mom for her birthday and this was a perfect afternoon. Not sure I would take my children (there were small children on board and they seemed bored after the first hour). But, the adults on board had a great time! We enjoyed our crew (Mike, Mike, Charlotte and Jenn). read more

I made the mistake of buying tickets six days in advance. 3 days before the trip, the weather report went from great to horrible. Hurricane Harvey was coming up this way and was going to dump a bunch of rain. I called them and explained that I'd be traveling with 6, 7, 83 and 85 year olds and had reservations about putting them on a boat in the pouring rain. I was bluntly told no changes allowed even due to weather. They had plenty of spaces available over the next few days. The day of the trip, I called 3 hours before departure time to get the status of the trip and was told that they just had a cruise come back and everyone had a great time sailing in the rain. Once again, no effort was made to accommodate my concerns or allow any changes. Once you buy a ticket, you either get on board for that trip or you're out of the money you spent. Yes, it was my fault for not paying close enough attention to the language on the ticket purchase page which says no changes, but this truly is a company that has no concern for its customers. According to the Weather Channel, it rained the entire time the trip was to take place. I don't regret making a responsible decision to keep my entire family out of that mess and I certainly won't regret sending this company any more money. read more

Very disappointing!!! I had a very expensive gift card ($124) that they would not honor when I called for a reservation. It came attached to their greeting card with a picture of the ship on the front, and unknown to me, I had to remove the gift card to read the very fine print on the back about expiration. Very disappointing policy and no loyalty to customers, especially since I'd been on 3 other expensive previous cruises. Buyer of Schooner Woodwind gift cards, beware!!! read more

Went out with a group of gals for part of a bachelorette weekend. A great sailing cruise! It was a little crowded for my liking but it was high summer. I wish we could have done a private one but that was not in the budget! Definitely worth doing! read more

Wonderful Sunset evening cruise. Helpful crew, easy ticketing & boarding. Delightful history talk and great selection of craft brews. Look forward to going again in the future. read more

What a fabulous experience! We picked an amazing day to be on the water and had the time of our lives. Captain Jen and her crew were fantastic - friendly, helpful and fun. The boat is beautiful and we enjoyed the chance to take the helm. Will definitely go again and bring a bigger crowd with us! read more

Such a great activity to do in Annapolis, $40 per person for 2 hours was well worth it and honestly, the most economical sail I could find in Annapolis! Great crew and captain made sure we had a great time! Only down fall is that it gets very crowded on the boat, so just make sure to be one of the first in line for boarding to make sure you get a good seat! Love love loved our time on the Schooner Woodwind! read more

Jen and the crew were amazing and courteous! I would do this again in a heartbeat! Highly reccomended for anyone!

We purchased our tickets for the sunset sail on this Schooner for Saturday, June 27, 2015. The weather forecast for the day was at 100% rain with strong thunderstorms. The weather advisory also asks that no boats be in the water because of unsafe conditions. Well just as the weather predicted, it rained cats and dogs all day. The Schooner's policy states that they will not refund any customer's money unless the captain cancels the sail. Despite the weather warnings and unsafe conditions, the Schooner refused to cancel the sail and took the boat out anyway. Passengers were forced to lose their money or sit on the wet boat with the rain pouring down on them as well as risk their lives with the possibility of lighting and thunderstorms. This lack of sensitivity and poor customer service is just outrageous! I used to rave about this Schooner but after today, it is clear that this company is more concerned about the almighty dollar than the safety and satisfaction of its customers. read more

***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 Watermark!!! read more